Oakland Vacation Rentals, Homes, & More

Oakland (196) Filter Cancel

1-50 of 196 Oakland Rentals

| View All
Sort:
1  2  3  4  View All
Oakland Maryland Vacation Rentals - Cottage
1 / 24

Oakland Cottage
2 Bedrooms / 1 Bathroom / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$125

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$125 - $173
Per month:$3,750 - $5,190
Pets allowed:Yes
Internet:Yes

Now 3rd Night FREE! Reserve Today! Fox Den Lake House is an affordable, year- round, 2- bedroom, 1- bath vacation rental home with views of Deep Creek Lake from every room. Walk across the road to rent a boat or take a quick stroll down the street for some ice cream and nice...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 29

Oakland Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

from

$300

/ night

Email Owner
Bedrooms:5
Bathrooms:4.5
Sleeps:14
Type:Home
Per night:$300 - $648
Per month:$9,000 - $19,440
Pets allowed:No
Internet:Yes

20% Discount for the Week of 7/19 thru 7/26/15! This exceptional home fronting Deep Creek Lake with a private dock, community pool, and so much more will make the perfect vacation spot! When you first see this home, you will say WOW! Walk under the cute covered front...

See more

Close x

Exterior
1 / 10

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

(5)“ Excellent ”5 Reviews

from

$742

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$742 - $1,106
Per month:$22,260 - $33,180
Pets allowed:No
Internet:No

Community: MountainsideBedding: King, King, King, King, KingValhalla "Hall of the Gods" is a spectacular 5 bedroom home that sits atop a beautiful mountain side. Step inside this wondrous home with large beams encompassing the great room and hardwoods that spread throughout the...

See more

Close x

Exterior
1 / 16

Oakland Cottage
3 Bedrooms / 4 Bathrooms / Sleeps 10
Cottage / 3 Bedrooms / Sleeps 10

(6)“ Excellent ”6 Reviews

from

$347

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Cottage
Per night:$347 - $662
Per month:$10,410 - $19,860
Pets allowed:Yes
Internet:No

Community: StockslagerBedding: King, Double & Double, Double, Double Sleeper SofaAngler's Cove is the perfect cottage for your lake vacation. Situated in the western end of the lake, Angler's Cove has access to a 2 mile walking trail that goes along the waterside for your morning...

See more

Close x

1 / 23

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(10)“ Excellent ”10 Reviews

from

$442

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$442 - $887
Per month:$13,260 - $26,610
Pets allowed:Yes
Internet:No

With a name like 180 Degrees, you should already know that this home features THE BEST views of Deep Creek Lake that are available. Located of off Glendale road, this immaculately furnished home offers unbeatable lakefront, a dock slip, and outdoor hot tub, the gas grill, a ...

See more

Close x

1 / 10

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

(7)“ Excellent ”7 Reviews

from

$473

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$473 - $691
Per month:$14,190 - $20,730
Pets allowed:No
Internet:No

Just high enough to host some of Deep Creek's finest views courtesy of your private balcony; just close enough to walk - not drive - to boating, dining, and shopping; and just private enough to feel that you are safely tucked away at the wood's edge - this gorgeous condominium...

See more

Close x

Exterior
1 / 16

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(10)“ Excellent ”10 Reviews

from

$312

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$312 - $437
Per month:$9,360 - $13,110
Pets allowed:No
Internet:No

Community: BlakesleeBedding: King, King, Queen, Queen Sleeper Sofa, Queen Sleeper SofaCome and relax at San~Stress, located in the wonderful community of Blakeslee. This property is adorned with hardwood floors, tongue and groove ceilings, and plenty of space for the whole ...

See more

Close x

1 / 15

Oakland Home
8 Bedrooms / 7 Bathrooms / Sleeps 26
Home / 8 Bedrooms / Sleeps 26

(7)“ Excellent ”7 Reviews

from

$462

/ night

Email Owner
Bedrooms:8
Bathrooms:7
Sleeps:26
Type:Home
Per night:$462 - $862
Per week:$3,234 - $6,031
Pets allowed:Yes
Internet:Yes

Avoid the ordinary! Thrilling Blueberry Hill is the pinnacle of vacation perfection. Ideally located, this charming pet friendly chalet is within a short stroll to restaurants, and within 3 miles of the state park, movie theaters, and other lake activities. Relax in lakefront...

See more

Close x

1 / 13

Oakland Home
6 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 6 Bedrooms / Sleeps 14

(8)“ Very Good ”8 Reviews

from

$348

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:14
Type:Home
Per night:$348 - $677
Per week:$2,434 - $4,737
Pets allowed:Yes
Internet:Yes

Anytime is the perfect time to vacation at this striking pet friendly mountain chalet! Sunbathe and water ski in the warm summer months, crunch through carpets of multi- colored leaves in the glorious fall months, ski in a true winter wonderland filled with pristine snow and watch...

See more

Close x

1 / 13

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(9)“ Excellent ”9 Reviews

from

$302

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$302 - $728
Per week:$2,109 - $5,091
Pets allowed:No
Internet:Yes

Let yourself be transported by Lake Shore Dreams to a place where the pace is a little slower, the stars shine brighter and air is crisp and clear. You’ll awake feeling completely refreshed and ready to tackle the many activities that are at your fingertips. Enjoy boating, swimming...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
4 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

(3)“ Excellent ”3 Reviews

from

$262

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$262 - $545
Per week:$1,834 - $3,809
Pets allowed:No
Internet:Yes

Tucked at the end of quiet Lakeforest Drive, Glistening Waters lives up to its name. A nice level lakefront greets you as you walk out the front door. Trees surround the area to provide privacy and serenity. Inside, you will find fresh décor and quality furnishings to make you ...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 13
Home / 5 Bedrooms / Sleeps 13

(1)“ Excellent ”1 Review

from

$308

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:13
Type:Home
Per night:$308 - $686
Per week:$2,152 - $4,801
Pets allowed:Yes
Internet:Yes

This beautiful pet friendly log chalet offers the charm and esthetic appeal of yesteryear with all the contemporary amenities to pamper you. Superb lakefront, just 50 yards from the deck, offers a grass covered yard with just a speckling of trees and a panoramic view. Your family...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
4 Bedrooms / 4 Bathrooms / Sleeps 11
Home / 4 Bedrooms / Sleeps 11

from

$243

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:11
Type:Home
Per night:$243 - $318
Per week:$1,701 - $2,220
Pets allowed:No
Internet:No

Providence at Penn Cove will make the perfect destination for an unforgettable Deep Creek getaway! The beautifully landscaped backyard with a small pond and fire pit is a great spot to relax or venture out to the lake access and head out on the water! Inside the home offers comfortable...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(6)“ Excellent ”6 Reviews

from

$361

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$361 - $603
Per week:$2,523 - $4,218
Pets allowed:No
Internet:Yes

Walls of windows showcase spectacular, up close, lake views from every room! This spacious home boasts the finest of materials from the kitchen and baths to the large screen TV surround sound systems. Everyone will be eager to go outside to play when they see the grassy level lawn...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(2)“ Excellent ”2 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$250 - $475
Per week:$1,747 - $3,321
Pets allowed:No
Internet:Yes

Come find rest and rejuvenation at Bear Cove! This spacious three bedroom is settled back on a quiet section of the lake where you can stroll on community roads or relax by the quiet cove. The hot tub even has a great view and there is a firepit for campfire songs and late night ...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(3)“ Excellent ”3 Reviews

from

$209

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$209 - $359
Per week:$1,460 - $2,513
Pets allowed:No
Internet:Yes

Paradise peppered with ambiance - - - Baldwins Domain is the perfect choice for the discerning guest. Linger for a moment on the spacious decks of this elegant home located in the prestigious community of Blakeslee. The superbly decorated rooms are accented with cozy comforters and...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 9

Oakland Home
4 Bedrooms / 4 Bathrooms / Sleeps 14
Home / 4 Bedrooms / Sleeps 14

(9)“ Excellent ”9 Reviews

from

$697

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Home
Per night:$697 - $1,125
Per month:$20,910 - $33,750
Pets allowed:No
Internet:No

If refreshment is what a vacation is all about, then this bright and spacious lakefront will provide all that you will need. Cathedral ceiling, stone fireplace and soaring glass windows provide a wonderful view of the woodsy back yard. Take a short stroll down a lighted path to ...

See more

Close x

1 / 10

Oakland Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

(4)“ Very Good ”4 Reviews

from

$422

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$422 - $478
Per month:$12,660 - $14,340
Pets allowed:Yes
Internet:No

Enjoy the original cabin at Deep Creek Lake, family owned for over 60 years! This home is complete with a fireplace and post & beam ceilings in the living room. This home has all the luxuries of home - flat screen TV & internet with all the comforts of Deep Creek. Lakefront...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 9

Oakland Home
3 Bedrooms / 1 Bathroom / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

from

$207

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:10
Type:Home
Per night:$207 - $297
Per month:$6,210 - $8,910
Pets allowed:No
Internet:No

Bedding: Queen, Queen & Twin, Double & Twin, Queen Air MattressA lifetime of memories is waiting for you and your family when you choose the enchanting home Restintyme for you next stay at Deep Creek Lake. Unique in design, this delightful 3 bedroom home is ideal for the small...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 20

Oakland Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$355

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$355 - $411
Per month:$10,650 - $12,330
Pets allowed:Yes
Internet:No

This charming home accented with antiques will hug you when you walk through the door. Located near Swallow Falls State Park, Herrington Manor State Park and minutes from Deep Creek Lake; this home offers a great location for local activities and events, or just stay back and relax...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 10

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 13
Home / 5 Bedrooms / Sleeps 13

(7)“ Excellent ”7 Reviews

from

$467

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:13
Type:Home
Per night:$467 - $621
Per month:$14,010 - $18,630
Pets allowed:No
Internet:Yes

Come out of your shell and stay at Terp's Hideaway. This chalet is sure to please. You can kick back and relax with all your friends and watch your favorite sport on TV from the comfort of two family areas. Play a fun filled game of pool, or just sit and watch your favorite movie....

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 11

Oakland Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$305

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$305 - $412
Per month:$9,150 - $12,360
Pets allowed:No
Internet:No

Bedding: King, King, King, 2 Bunk BedPrepare for the “Wow! ” when you walk into the breathtaking home known as Log Hut! The newly renovated 4 bedroom log home offers the best of both worlds both inside and out. The interior design that flows consistently throughout the home...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 20

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

from

$318

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$318 - $732
Per week:$2,224 - $5,122
Pets allowed:No
Internet:No

Good Times, Great Friends. Memories are made in this spacious home. There is plenty of room for family gatherings or it provides a good reason to schedule a vacation away with old friends. This home is a great choice year round with nice lake frontage and only a short drive to the...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
4 Bedrooms / 5 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

from

$374

/ night

Email Owner
Bedrooms:4
Bathrooms:5
Sleeps:12
Type:Home
Per night:$374 - $697
Per week:$2,612 - $4,874
Pets allowed:Yes
Internet:No

This beautiful lake home instantly welcomes you as you arrive with a natural stone fireplace reaching up to cathedral ceilings and windows looking out to the mountain surroundings and Deep Creek Lake. Exquisite furnishings and unique architectural features throughout create an elegant...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(2)“ Very Good ”2 Reviews

from

$437

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:14
Type:Home
Per night:$437 - $697
Per month:$13,110 - $20,910
Pets allowed:No
Internet:No

Bedding: King, King, King, Duobunk and Bunk, Duobunk and bunk, QueenSpectacular plush country views will mesmerize you with their splendor when you stay in the magnificent log home known as Log Mahal. This custom crafted 5 bedroom home will quickly win you over with it's unique...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(13)“ Excellent ”13 Reviews

from

$447

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$447 - $897
Per month:$13,410 - $26,910
Pets allowed:No
Internet:No

Community: StockslagerBedding: King, Queen, Queen, Queen, Double Air MattressTake your dream vacation at the luxurious Oz, located in the western part of Deep Creek Lake. Oz is the grand of lakefront properties with exquisite decor, a spacious layout, and fantastic ambiance....

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 7

Oakland Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(5)“ Excellent ”5 Reviews

from

$311

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$311 - $380
Per month:$9,330 - $11,400
Pets allowed:Yes
Internet:No

Four Seasons home conveniently located in a quiet neighborhood. Deep Creek Lake State Park is just down the road with playgrounds and a sandy beach for the children to enjoy. Enjoy a State Park Pass giving up to 10 members of your party free access to any of Garrett Counties numerous...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 8

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$297

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:12
Type:Home
Per night:$297 - $387
Per month:$8,910 - $11,610
Pets allowed:No
Internet:No

Community: Roman RidgeBedding: Queen, Queen, Queen, Queen, 2 Twins, Double FutonCaesar’s Hideaway is a warm and inviting home that is designed with the ease of entertainment in mind. Located in the heart of Deep Creek Lake, you and your guests will love the convenient location...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(4)“ Excellent ”4 Reviews

from

$194

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$194 - $322
Per week:$1,353 - $2,251
Pets allowed:Yes
Internet:Yes

The epitome of convenience inside and out, Quality Time combines an ideal location with classic décor and an array of amenities. Spend time with the important people in your life including the family dog while chatting by the fire or relaxing under the stars on the deck. Within ...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 17

Oakland Home
2 Bedrooms / 1 Bathroom / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

from

$217

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$217 - $287
Per month:$6,510 - $8,610
Pets allowed:No
Internet:No

Bedding: Queen, Queen, Queen Sleeper SofaRich in Deep Creek history, this cottage was built as company housing for Deep Creek’s Hydro Electric Dam workers in 1925. Featuring private Youghiogheny River frontage in the protected Wild and Scenic Corridor, this home is completely...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
3 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(14)“ Excellent ”14 Reviews

from

$249

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
Per night:$249 - $382
Per month:$7,470 - $11,460
Pets allowed:No
Internet:No

Community: MountainsideBedding: Queen, Queen, Queen, 2 Queen Sleeper SofasIs the clamor of city life wearing you down? Cedarwoods, a stunning 3 bedroom mountain chalet, is calling your name. Nestled away in the quiet community of Mountainside, this beautiful home offers the ...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 17

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(1)“ Excellent ”1 Review

from

$259

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$259 - $456
Per week:$1,809 - $3,187
Pets allowed:No
Internet:No

This five bedroom, newly constructed home will wow you at every turn! Located on a quiet cove on Deep Creek Lake, your private dock and slip are just a short walk across the street. Bear Foot Cove features a massive deck, which is ideal for group meals, sun bathing, and enjoying...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 15

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(16)“ Excellent ”16 Reviews

from

$271

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:14
Type:Home
Per night:$271 - $424
Per week:$1,895 - $2,965
Pets allowed:Yes
Internet:Yes

A place of repose, a place to reflect and to rekindle the spirit- - - that is the American Dream. Located on a quiet wooded lot atop Mountainside, the view knows no end and the essence of privacy and quietude surround you. This beautiful chalet boasts four master suites, a prow...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
4 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

(5)“ Very Good ”5 Reviews

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$225 - $556
Per week:$1,569 - $3,887
Pets allowed:No
Internet:Yes

This lakefront Deep Creek vacation rental is truly spectacular. Complete with elegant furnishings and décor, and picture- perfect lake views, Harmony offers wonderful indoor and outdoor living spaces. With 4 bedrooms and 3 baths, this home can sleep up to 12 people. Enjoy a large...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 12

Oakland Home
5 Bedrooms / 4 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(8)“ Excellent ”8 Reviews

from

$194

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:14
Type:Home
Per night:$194 - $324
Per week:$1,353 - $2,262
Pets allowed:No
Internet:Yes

Perfectly situated in the heart of it all, Crosswinds combines ideal location with the right blend of comfort and style. Within a short walk you’ll find Silver Tree marina – the next best thing to having your own dock slip. Drive just a few miles further to reach state parks,...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
9 Bedrooms / 8 Bathrooms / Sleeps 28
Home / 9 Bedrooms / Sleeps 28

(14)“ Excellent ”14 Reviews

from

$922

/ night

Email Owner
Bedrooms:9
Bathrooms:8
Sleeps:28
Type:Home
Per night:$922 - $1,437
Per week:$6,452 - $10,057
Pets allowed:No
Internet:Yes

If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable when it comes to your comfort and pleasure. This exquisite log home masterpiece offers 100 feet of beautiful lakefront decorated with fragrant mountain laurel and towering...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

(7)“ Excellent ”7 Reviews

from

$470

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$470 - $768
Per month:$14,100 - $23,040
Pets allowed:Yes
Internet:No

This home is just what you need to create your families own golden memories. This park style atmosphere is perfect for your friends, family and Dog! Soak in the hot tub and enjoy a Lake view, play and picnic by the lake, or jump on your boat from your private dock and have some...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$657

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Home
Per night:$657 - $704
Per week:$4,595 - $4,925
Pets allowed:No
Internet:No

Bedding: King, King, Queen, Queen, Bunk and 2 TwinsYour Deep Creek adventure awaits! Reverie is an exquisite 5 bedroom home that will far exceed your expectations. Floor to ceiling windows in the Great Room allow you and your guests to bask in the sheer beauty of the lake from...

See more

Close x

Oakland Maryland Vacation Rentals - Apartment
1 / 8

Oakland Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$175 - $280
Per month:$5,250 - $8,400
Pets allowed:No
Internet:No

Community: Red RunBedding: King, 2 Twins, 2 Twins, Queen Sleeper SofaRed Run 1A3 is an alluring 3 bedroom condominium located in the desirable Red Run Community. Summer days don't get better than this as you and your guests relish time spent swimming & playing from the nearby beach...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 19

Oakland Home
5 Bedrooms / 5 Bathrooms / Sleeps 14
Home / 5 Bedrooms / Sleeps 14

(1)“ Very Good ”1 Review

from

$537

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:14
Type:Home
Per night:$537 - $1,137
Per month:$16,110 - $34,110
Pets allowed:No
Internet:No

Community: BlakesleeBedding: King; Queen; Queen; Queen; Queen; Double Futon; Queen Sleeper SofaThere is no better place to reunite with friends and family than Nature’s Retreat. This spectacular 5 bedroom lakefront home offers all of the amenities of home and more! Glistening...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
5 Bedrooms / 6 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

(5)“ Excellent ”5 Reviews

from

$353

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$353 - $732
Per week:$2,469 - $5,124
Pets allowed:No
Internet:Yes

Experience the thrill of lakefront living at this spectacular new retreat. Lake Shore Lodge brims with the promise of vacation memories that will last a lifetime. With two fireplaces and an outdoor hot tub, there’s definitely no shortage on fun. Just yards from the water’s edge,...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

(5)“ Excellent ”5 Reviews

from

$227

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Home
Per night:$227 - $600
Per week:$1,586 - $4,196
Pets allowed:No
Internet:Yes

A gorgeous lake view greets you as you enter this beautiful chalet located on the very desirable Paradise Point peninsula. Relax on the expansive redwood decks and survey the virtually unobstructed view of the glistening waters of Deep Creek. Emerald Bay offers a large, level lakefront...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 21

Oakland Home
7 Bedrooms / 7 Bathrooms / Sleeps 18
Home / 7 Bedrooms / Sleeps 18

from

$725

/ night

Email Owner
Bedrooms:7
Bathrooms:7
Sleeps:18
Type:Home
Per night:$725 - $1,225
Per month:$21,750 - $36,750
Pets allowed:Yes
Internet:No

Bedding: King, King, King, Queen, Queen, Queen, Queen, 2 Double RollawaysIf you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
8 Bedrooms / 9 Bathrooms / Sleeps 24
Home / 8 Bedrooms / Sleeps 24

(12)“ Excellent ”12 Reviews

from

$979

/ night

Email Owner
Bedrooms:8
Bathrooms:9
Sleeps:24
Type:Home
Per night:$979 - $1,229
Per week:$6,848 - $8,597
Pets allowed:No
Internet:Yes

Elegant, Extravagant, Extraordinary…and the list goes on! Uncommon quality can be found in the smallest details of this grand chalet. Possessing a spectacular, sweeping view of Deep Creek Lake and its lush mountains, Peregrine’s Perch is a premium home that is flawless in...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 14

Oakland Home
6 Bedrooms / 4 Bathrooms / Sleeps 16
Home / 6 Bedrooms / Sleeps 16

(9)“ Excellent ”9 Reviews

from

$340

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:16
Type:Home
Per night:$340 - $758
Per week:$2,380 - $5,302
Pets allowed:Yes
Internet:Yes

Beautifully decorated with a woodland theme, this pet friendly lakefront resort home is one of a kind. Treat your family and friends to such amenities as pool table, hot tub, large rooms and quality furnishings. Your dog will love the screened porch, spacious decks with plenty...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 22

Oakland Home
3 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 3 Bedrooms / Sleeps 12

(7)“ Excellent ”7 Reviews

from

$403

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:12
Type:Home
Per night:$403 - $574
Per month:$12,090 - $17,220
Pets allowed:Yes
Internet:No

This luxurious lake access vacation home will afford you an exclusive, and may we add, spectacular, bird's eye view of Deep Creek Lake. A spacious kitchen and dining area, an inviting great room, a fun- packed game room, and oh so comfortable bedrooms - with views to positively...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 16

Oakland Home
5 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

(13)“ Excellent ”13 Reviews

from

$249

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Home
Per night:$249 - $565
Per week:$1,741 - $3,954
Pets allowed:No
Internet:Yes

"What would you say to the perfect lakefront home, in the perfect location, with the perfect list of amenities?" You would say “Aah, Chalet! ” You can have it all at this fantastic retreat. Watch the sparkling lake as you soak in the new hot tub, relax in the loft, or play...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 13

Oakland Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(3)“ Excellent ”3 Reviews

from

$329

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$329 - $648
Per month:$9,870 - $19,440
Pets allowed:Yes
Internet:No

NEW STEREO WITH IPOD DOCK Bee Tree II is a log cabin style home nestled in a quiet cove on the shores of Deep Creek Lake. You will be able to enjoy all of the area’s four seasons on this home’s wooded lot. This is the perfect place to enjoy a snowy day, through a line in the ...

See more

Close x

Oakland Maryland Vacation Rentals - Home
1 / 18

Oakland Home
6 Bedrooms / 5 Bathrooms / Sleeps 17
Home / 6 Bedrooms / Sleeps 17

(14)“ Excellent ”14 Reviews

from

$558

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:17
Type:Home
Per night:$558 - $772
Per week:$3,901 - $5,400
Pets allowed:Yes
Internet:Yes

Packed with amenities, Splash Mountain offers a spacious vacation home with superior looks inside and out. Situated atop Marsh Mountain on an expansive 3 ½ acres, this Deep Creek rental offers privacy and stuffing views. The home offers 6 bedrooms, as well as a state- of- the-...

See more

Close x

1  2  3  4  View All
1234View All
page 1 of 4
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More