Orleans Vacation Rentals

127 Rentals

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Orleans Massachusetts Vacation Rentals - 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
Orleans Massachusetts Vacation Rentals - Home

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

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Orleans Home

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

$193 - $286 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 5 - Orleans Home

Property ID: 18392 / Key #: 419 / Property Name: 8 Hofe RoadSpacious ranch minutes away from Skaket Beach...

$108 - $143 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Orleans Home

Under 1 mile to Skaket BeachJust under 1 mile to Skaket Beach from this beautiful 3 bedroom, 3 bath...

$400 / nt

Orleans Massachusetts Vacation Rentals - Home

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 / 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

NEW LISTING! This lovely new Contemporary Cape sits on almost an acre of land only 2/10ths of a mile...

$229 - $286 / 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

2BR / 1BA - Sleeps 4 - Orleans Home

Located in the desirable Tonset area of East Orleans, this light and bright cottage is a great Cape...

$129 - $186 / 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

3BR / 2BA - Sleeps 6 - Orleans Home

Located right on the shore of beautiful Town Cove in Orleans. This family home has 3 bedrooms 2 baths...

$429 - $500 / 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 / 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

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

4BR / 3BA - Sleeps 8 - Orleans Home

Property ID: 18543 / Key #: 183 / Property Name: 26 Winslow DriveLocated in South Orleans and close to...

$350 - $408 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Orleans Home

15 Mill Pond Road, Orleans, MABeautifully decorated home in the desirable Mill Pond area and with central...

$479 - $515 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Orleans Home

Lovely dog friendly home in East OrleansFresh new listing in East Orleans with central A/C. Walk to restaurants...

$215 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

30 HARBOR HILL ORLEANSClose to the bike path and just a short drive to Rock Harbor and Skaket Beaches....

$186 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 6 - Orleans Home

Waterfront on Nauset Harbor! Classic Cape located on an incredible property overlooking the water and...

$300 - $429 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Orleans Home

This wonderful 4- bedroom, dog- friendly, vacation home is located only 200 yards from Skaket Beach....

$172 - $429 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 2BA - Sleeps 8 - Orleans Home

Comfortable 4 bedroom home located on a quiet dead end road just a short distance from Rock Harbor and...

$143 - $215 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Orleans Home

Bright, open and very spacious Cape centrally located on a cul- de- sac not far from Skaket Beach,...

$286 - $315 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Orleans Home

Completely renovated, absolutely gorgeous, Sea Captain's home located on over an acre in the highly...

$486 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Orleans Home

Wonderful custom home with all the amenities- - only a half- mile from Pah Wah Pond and its conservation...

$400 - $515 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 1BA - Sleeps 6 - Orleans Home

10 Daley TerraceThis quaint & cozy ranch is set on a hill in a residential neighborhood & within walking...

$115 - $172 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 10 - Orleans Home

This charming and pristine contemporary ranch, nestled in a private wooded paradise- Mayflower Point,...

$300 - $400 / nt

Orleans Massachusetts Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Orleans Home

At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet...

$186 - $386 / nt

Orleans Massachusetts Vacation Rentals - Home

4BR / 3BA - Sleeps 8 - Orleans Home

Very spacious and nicely appointed home perfect for the larger get- together. Located on a wooded lot...

$236 - $293 / nt

Orleans Massachusetts Vacation Rentals - Home

6BR / 2BA - Sleeps 8 - Orleans Home

Nauset Heights! Classic Cape Cod beach house overlooking the Atlantic. Expansive great room with fieldstone...

$558 - $658 / nt

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