Oakland Vacation Rentals

200 Rentals

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3BR / 2BA - Sleeps 8 - Oakland Cottage

Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat...

$586 - $1,098 / nt

Exterior

2BR / 1BA - Sleeps 6 - Oakland Home

Bedding: Queen, Queen, Queen Sleeper SofaLocated in the heart of the action, you and the family will...

$162 - $197 / nt

4BR / 3BA - Sleeps 10 - Oakland Home

This beautiful Deep Creek Lake chalet will be the remedy to all of your vacation troubles! The classic...

$179 - $334 / nt

Exterior

5BR / 3BA - Sleeps 12 - Oakland Home

Bedding: King, King, Queen, Queen, Double & BunkHigher Ground is a gorgeous five- bedroom chalet...

$297 - $472 / nt

Exterior

3BR / 2BA - Sleeps 6 - Oakland Cottage

Bedding: Queen, Double, 3 TwinsTucked away in a quiet secluded cove at the Southern end of Deep Creek...

$212 - $357 / nt

Deck View

3BR / 3BA - Sleeps 10 - Oakland Home

Bedding: Queen, Queen, Queen & Bunk w/trundle, Queen, Twin Sleeper SofaDeep Creek adventures are...

$237 - $375 / nt

Exterior

4BR / 4BA - Sleeps 10 - Oakland Home

Bedding: Queen, King, Queen, 2 Twins, Queen Air MattressClear View is a spectacular 4 bedroom lakefront...

$382 - $797 / nt

5BR / 6BA - Sleeps 14 - Oakland Home

Let yourself be transported by Lake Shore Dreams to a place where the pace is a little slower, the stars...

$302 - $728 / nt

Oakland Maryland Vacation Rentals - Home

5BR / 5BA - Sleeps 14 - Oakland Home

Community: BlakesleeBedding: King; Queen; Queen; Queen; Queen; Double Futon; Queen Sleeper SofaThere...

$497 - $1,125 / nt

5BR / 5BA - Sleeps 14 - Oakland Home

Pine Oasis offers everything one could need for a relaxing Deep Creek Lake vacation. This lakefront home...

$263 - $620 / nt

3BR / 4BA - Sleeps 10 - Oakland Home

Come find rest and rejuvenation at Bear Cove! This spacious three bedroom is settled back on a quiet...

$250 - $475 / nt

6BR / 5BA - Sleeps 17 - Oakland Home

Packed with amenities, Splash Mountain offers a spacious vacation home with superior looks inside and...

$558 - $772 / nt

5BR / 3BA - Sleeps 12 - Oakland Home

LinLaurAl is a five- bedroom Deep Creek vacation rental that has a little bit of everything. Featuring...

$254 - $493 / nt

4BR / 4BA - Sleeps 12 - Oakland Home

Lose yourself in the beauty of nature at R&R; Escape. Featuring a wall of windows in the great room,...

$225 - $337 / nt

Oakland Maryland Vacation Rentals - Home

4BR / 3BA - Sleeps 12 - Oakland Home

Bedding: King, Queen, Queen, 2 Bunks with Twin TrundlesLet the adventure begin! Mother Nature will...

$325 - $647 / nt

Exterior

2BR / 1BA - Sleeps 6 - Oakland Home

Bedding: Queen, Queen, Queen Sleeper SofaRich in Deep Creek history, this cottage was built as company...

$212 - $277 / nt

5BR / 3BA - Sleeps 12 - Oakland Home

"What would you say to the perfect lakefront home, in the perfect location, with the perfect list of...

$239 - $565 / nt

5BR / 4BA - Sleeps 14 - Oakland Home

Perfectly situated in the heart of it all, Crosswinds combines ideal location with the right blend of...

$194 - $324 / nt

Exterior

5BR / 5BA - Sleeps 12 - Oakland Home

Bedding: Queen, Queen, Queen, Queen, 2 Bunk BedsSurround yourself with nature in this majestic log...

$462 - $977 / nt

Oakland Maryland Vacation Rentals - Home

5BR / 3BA - Sleeps 12 - Oakland Home

Bedding: King, King, Queen, Queen, 2 Twins w/T TrundlesWelcome View Point is a warm and captivating...

$447 - $887 / nt

Oakland Maryland Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Oakland Home

Community: MountainsideBedding: King, King, Queen, Queen, Queen Sleeper SofaJoy of Living is a Deep...

$377 - $647 / nt

7BR / 7BA - Sleeps 18 - Oakland Home

Life is full of surprises an you will find the most wonderful ones at Hollywood! Recently completely...

$531 - $864 / nt

6BR / 4BA - Sleeps 16 - Oakland Home

Beautifully decorated with a woodland theme, this pet friendly lakefront resort home is one of a kind....

$336 - $758 / nt

6BR / 6BA - Sleeps 15 - Oakland Home

Visualize yourself standing at the railing of a spacious, sunlit deck, as you survey the expansive...

$339 - $765 / nt

Oakland Maryland Vacation Rentals - Home

2BR / 2BA - Sleeps 6 - Oakland Home

Enter a world of soft winds and crystal waters at this charming pet friendly cottage. The delightful...

$165 - $301 / nt

Oakland Maryland Vacation Rentals - Home

8BR / 6BA - Sleeps 22 - Oakland Home

Put an end to vacation disappointment at shining pet friendly Lake’s End! Busy minds and talented...

$453 - $841 / nt

5BR / 6BA - Sleeps 14 - Oakland Home

A place of repose, a place to reflect and to rekindle the spirit- - - that is the American Dream. Located...

$271 - $424 / nt

Oakland Maryland Vacation Rentals - Home

5BR / 6BA - Sleeps 12 - Oakland Home

Bedding: Queen, Queen, Queen, Queen, 2 Twins, Double FutonCaesar’s Hideaway is a warm and inviting...

$297 - $412 / nt

Oakland Maryland Vacation Rentals - Home

3BR / 2BA - Sleeps 10 - Oakland Home

Community: StockslagerBedding: King, King, Queen, Queen Sleeper Sofa, 2 Twin RollawaysPrepare to...

$312 - $462 / nt

4BR / 3BA - Sleeps 9 - Oakland Home

From the moment you enter the private tree- lined drive, you'll be enchanted with all Sunrise has to...

$178 - $379 / nt

Oakland Maryland Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Oakland Home

Trail’s End is situated on a 4- acre lot with over 120 feet of spectacular lakefront. This stylish...

$177 - $391 / nt

3BR / 3BA - Sleeps 8 - Oakland Home

Paradise peppered with ambiance - - - Baldwins Domain is the perfect choice for the discerning guest....

$209 - $359 / nt

6BR / 4BA - Sleeps 16 - Oakland Home

If it’s a breathtaking view that you’re looking for, you’ll find it at Scenic Overlook. Truly...

$236 - $393 / nt

Oakland Maryland Vacation Rentals - Home

9BR / 8BA - Sleeps 28 - Oakland Home

If bigger is better, this fantastic chalet is the absolute best! Timberlodge excels in every way imaginable...

$922 - $1,437 / nt

4BR / 3BA - Sleeps 10 - Oakland Home

Tucked among the trees, Blue Spruce is the perfect place to relax and lose your self in the beauty of...

$185 - $457 / nt

Oakland Maryland Vacation Rentals - Home

3BR / 4BA - Sleeps 10 - Oakland Home

Community: BlakesleeBedding: King, King, Queen, Queen Sleeper Sofa, Queen Sleeper SofaCome and relax...

$305 - $412 / nt

Oakland Maryland Vacation Rentals - Home

5BR / 6BA - Sleeps 16 - Oakland Home

Rother's Cove is a long time favorite that has undergone extensive updates that include the addition...

$338 - $710 / nt

3BR / 2BA - Sleeps 12 - Oakland Home

Located in the prestigious community of Blakeslee, this marvelous pet friendly chalet offers numerous...

$147 - $248 / nt

Oakland Maryland Vacation Rentals - Home

4BR / 5BA - Sleeps 12 - Oakland Home

This beautiful lake home instantly welcomes you as you arrive with a natural stone fireplace reaching...

$356 - $697 / nt

Oakland Maryland Vacation Rentals - Home

4BR / 3BA - Sleeps 12 - Oakland Home

Located in the picturesque Silver Ridge community, this Craftsman style home is the epitome of style....

$214 - $263 / nt

5BR / 3BA - Sleeps 12 - Oakland Home

A gorgeous lake view greets you as you enter this beautiful chalet located on the very desirable Paradise...

$227 - $600 / nt

5BR / 3BA - Sleeps 14 - Oakland Home

Amazing Love is the ultimate lakefront home that is sure to fit your Deep Creek vacation needs. This...

$225 - $491 / nt

4BR / 4BA - Sleeps 10 - Oakland Home

This lovely 4 bedroom Deep Creek home is decorated with the finest furnishings in a comfortable and cozy...

$230 - $303 / nt

Oakland Maryland Vacation Rentals - Home

6BR / 5BA - Sleeps 15 - Oakland Home

Vibrant and uplifting, Tamaqua Lodge will lift your spirits to new heights. Beautifully appointed rooms...

$308 - $625 / nt

4BR / 3BA - Sleeps 10 - Oakland Home

Leisure time takes on a whole new meaning when you spend time at Just Breathe Inn! Your agenda is certain...

$194 - $382 / nt

Oakland Maryland Vacation Rentals - Home

7BR / 7BA - Sleeps 18 - Oakland Home

Bedding: King, King, King, Queen, Queen, Queen, Queen, 2 Double RollawaysIf you are seeking a...

$725 - $1,187 / nt

Oakland Maryland Vacation Rentals - Cottage

2BR / 2BA - Sleeps 4 - Oakland Cottage

Community: Yellowstone VillageBedding: King, KingTree Haus is a Yellowstone Log home nestled in a fabulous...

$249 - $337 / nt

6BR / 6BA - Sleeps 14 - Oakland Home

Anytime is the perfect time to vacation at this striking pet friendly mountain chalet! Sunbathe and...

$348 - $677 / nt

Oakland Maryland Vacation Rentals - Home

5BR / 6BA - Sleeps 14 - Oakland Home

Its All Good will help you to release the stresses of life and recharge your batteries. This lake area...

$255 - $330 / nt

Oakland Maryland Vacation Rentals - Home

2BR / 2BA - Sleeps 7 - Oakland Home

Leisure is yours to be had at Vista on the Lake. This cozy, pet friendly cottage is the perfect getaway...

$162 - $280 / nt

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