Orleans Vacation Rentals

211 Rentals

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Front of Home
Tchc

4BR / 2BA - Sleeps 8 - Orleans Home

This gorgeous home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you...

$343 - $543 / nt

1 Review
Orleans Massachusetts Vacation Rentals - Home
Julie

3BR / 2BA - Sleeps 8 - Orleans Home

Nauset beach is just down the road from this East Orleans Village, sun filled home. The quiet private...

$150 / nt

13 Reviews
Front of house

4BR / 3BA - Sleeps 10 - Orleans Home

27 Pond Road, OrleansNestled on a private 1. 5- acre wooded lot, this charming and newly constructed...

$286 - $486 / nt

Back of house overlooking Pleasant Bay

4BR / 2BA - Sleeps 8 - Orleans Home

41 Chestnut Drive - Waterfont on Pleasant Bay! Spend your vacation on a bluff overlooking Pleasant...

$193 - $286 / nt

4BR / 3BA - Sleeps 9 - Orleans Home

Property ID: 114251 / Key #: 2324 / Property Name: 21 Manito RoadLovely waterfront home on Meetinghouse...

$215 - $498 / nt

3BR / 2BA - Sleeps 8 - Orleans Home

JUST LISTED! ! ! Highest point on Nauset Heights with distant ocean views and choice of public or private...

$286 - $428 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Orleans Home

Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation...

$243 - $486 / nt

Orleans Massachusetts Vacation Rentals - Home

5BR / 4BA - Sleeps 10 - Orleans Home

Crystal Lake Waterfront! Enjoy fresh water swimming right outside your door! This wonderful, private...

$515 - $572 / nt

Orleans Massachusetts Vacation Rentals - Home

7BR / 4BA - Sleeps 10 - Orleans Home

Charming Antique home with 6 bedrooms plus a den providing accommodations for up to 10 guests. Two kitchens,...

$358 - $472 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Orleans Home

Recently renovated home tucked up on a knoll located in a very pleasant East Orleans neighborhood. The...

$229 - $343 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Orleans Home

Renovated ranch with lower level walkout tucked up on a hill in the lovely Brick Hill area of East Orleans....

$236 - $250 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Orleans Home

WATERFRONT on Bakers Pond! Contemporary home on 3 levels, all with water views! Bright and open throughout,...

$372 - $429 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Orleans Home

JUST LISTED! Classic Cape Cod beach cottage on a bluff overlooking Nauset Inlet and the Atlantic. This...

$458 - $572 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Orleans Home

Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded...

$372 - $415 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Enjoy the views overlooking Reuben’s Pond from this 3 bedroom, 2 bath contemporary saltbox offering...

$258 - $315 / nt

Orleans Massachusetts Vacation Rentals - Home

2BR / 3BA - Sleeps 6 - Orleans Home

'Rose Cottage' is an absolutely lovely, light and bright expanded cottage located on almost an acre...

$215 - $272 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Orleans Home

Location, Location! Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy,...

$165 - $200 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Orleans Home

Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly- furnished home...

$393 - $486 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy...

$193 - $258 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Orleans Home

Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on...

$172 - $272 / nt

Orleans Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Orleans Home

Clean, comfortable and cozy cottage overlooking Rock Harbor Marsh. Wonderful screened in porch for your...

$115 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Orleans Home

Cosy, welcoming home in South Eastham. Our traditional Cape Cod house features 4 bedrooms, 2 baths,...

$215 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Spotless home in a lovely quiet setting near the bike path. There are two living spaces and a first floor...

$143 - $215 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Lovely three bedroom contemporary Cape with an open floor plan located in a private cul de sac neighborhood....

$158 - $172 / nt

Orleans Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Orleans Home

Adorable updated two bedroom cottage with a bright screened in porch, outdoor shower and A/C units....

$129 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 14 - Orleans Home

This exceptional compound is one- of- a- kind with a Main House, Carriage House and private pool. The...

$572 - $1,358 / nt

Orleans Massachusetts Vacation Rentals - Home

5BR / 4BA - Sleeps 12 - Orleans Home

Spotless vacation home with in- ground pool. This home offers amenities and location at an affordable...

$458 - $500 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 7 - Orleans Home

This quintessential Cape Cod home was built in 1775 and has been in the same family for almost 200 years....

$258 - $286 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile...

$258 / nt

Orleans Massachusetts Vacation Rentals - Home

2BR / 0BA - Sleeps 6 - Orleans Home

Only 1. 8 miles to Nauset Beach and located In East Orleans Village! This renovated barn is private...

$136 - $165 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Bike to Ocean and Bay beaches from this Orleans vacation home. Beautiful 3 bedroom, 2 bathroom ranch...

$179 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Adorable cottage located in a wonderful East Orleans neighborhood near Mill Pond and Snow Shore Landing....

$140 - $186 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Orleans Home

Summer can t get any better than East Orleans. This private gem sits at the end of a sandy lane wrapped...

$200 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

NEW LISTING! Newly renovated sprawling ranch home located in the beautiful Briar Springs area of East...

$286 - $400 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Waterfront Beach Cottage, just bring your boat! You will love the deep water access right in your back...

$658 - $700 / nt

Orleans Massachusetts Vacation Rentals - Home

2BR / 1BA - Sleeps 4 - Orleans Home

Freshwater Lakefront! Wonderful, newly renovated cottage set on 1. 5 acres on Pilgrim Lake! Bright...

$158 - $250 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Orleans Home

12 Heritage DriveLovely, spacious colonial home near Pah Wah Pond and equidistant to Nauset Beach or...

$315 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 7 - Orleans Home

130 Portanimicut Rd, Orleans MAKayakers heaven! Spacious 3 bedroom - 3 bath home steps from a landing...

$258 - $386 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

5 Blueberry Island Road, Orleans, MABright and spacious home just a short distance to Cape Cod Bay...

$215 - $254 / nt

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