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Orleans Rentals

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From $1153 per night (USD)
VRBO
Beautiful East Orleans getaway with heated pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Set on a private manicured acre, but only a 5-minute drive to Nauset Beach. Sick of the beach? Relax at the heated swi ...
From $1153 per night (USD)
VRBO
From $653 per night (USD)
Expedia
“Compass Rose” in Orleans with Plunge Pool: 029-OC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. “Compass Rose” in Orleans with Plunge Pool Sleeps ...
From $653 per night (USD)
Expedia
From $354 per night (USD)
VRBO
WATERFRONT -Topside Boathouse - Swim and Fish off the Deck !
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Topside Boathouse Drift off to sleep to the gentle rhythm of waves beneath your bedroom window. Wake to spectacular sun ...
From $354 per night (USD)
VRBO
From $2014 per night (USD)
Expedia
ON THE WATER Topside Main House on Pleasant Bay. Sleeps 8, 3.5 baths.
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Right on the Water - Built by the present owner's grandfather in the 1930's, this home is as close to the water as you c ...
From $2014 per night (USD)
Expedia
$Walk to Beach, Home with Central A\/C. Private Acre+ Lot$
From $560 per night (USD)
VRBO
Walk to Beach, Home with Central A\/C. Private Acre+ Lot
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Walking distance to one of the most beautiful ocean beaches on Cape Cod , this beautiful, freshly remodeled Cape home si ...
From $560 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Kayaking, Swimming, and Shopping all within 3 miles!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 15575 - Bright Side : Kayaking, Swimming, and Shopping all within 3 miles! The Space: Experience life on the “ ...
From $305 per night (USD)
Expedia
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VRBO
The Beach House - Great Spot!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Call us so you don't miss out on this lovely Brewster vacation rental home, where it's all about the location! ...
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VRBO
From $416 per night (USD)
Expedia
Cottage near Cape Cod National Seashore with firepit, grill, kitchenette, & AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Cozy Escape on the Cape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $416 per night (USD)
Expedia
$Two-story home with private sauna, game room, work office, deck, grill, & W\/D$
From $537 per night (USD)
VRBO
Two-story home with private sauna, game room, work office, deck, grill, & W\/D
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $537 per night (USD)
VRBO
From $2199 per night (USD)
VRBO
Brand New Custom Home, Heated Pool, Pleasant Bay Access, Sleeps 12
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Sleep 12 Rents Friday to Friday during peak season Linens included Luxury living defined in East Orleans. This brand ne ...
From $2199 per night (USD)
VRBO
From $712 per night (USD)
VRBO
1 Minute Walk to Boat Meadow Landing!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 14515 - Tide Retreat: 1 Minute Walk to Boat Meadow Landing! The Space: Welcome to the tranquil town of Eastham ...
From $712 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Walk to Skaket Beach, Great Backyard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 15574 - Set Sail: Walk to Skaket Beach, Great Backyard! The Space: Conveniently located in Orleans, moments fr ...
From $474 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Modern Coastal Cottage in East Orleans: 009-OC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties Modern Coastal Cottage in East Orleans Sleeps 6 Li ...
From $352 per night (USD)
VRBO
From $609 per night (USD)
Expedia
BOATHOUSE on Pleasant Bay - swim, fish, kayak, etc. right off your front porch.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Like living on a yacht without the rocking - originally built to house boats, the Boathouse is cozy like a ship with wat ...
From $609 per night (USD)
Expedia
From $243 per night (USD)
VRBO
NEW Crystal Lake Contemporary Cottage!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
NEW LISTING! Crystal Lake Views & Dog Friendly*! * * * * See end of this description for information about ...
From $243 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Charming 2-bedroom cottage in wonderful Barley Neck area of Orleans with WiFi AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming cape cottage, 2 large bedrooms, oversized eat in kitchen, full bath, spacious living room with desk. A huge, su ...
From $417 per night (USD)
VRBO
From $1185 per night (USD)
VRBO
Luxury home located 2 min walk from Skaket Beach. Sunny, spacious and private.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This beautiful vacation home is located just a two minute walk from the popular Skaket Beach in Orleans, MA, a quaint se ...
From $1185 per night (USD)
VRBO
From $683 per night (USD)
Expedia
Association Beach less than a Mile away!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Summary: 15576: Rest a Shored - Association Beach less Than a Mile away! The Space: Within the serene enclave of Orlean ...
From $683 per night (USD)
Expedia
From $726 per night (USD)
VRBO
Town Cove Coastal Chic | 3 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located right on the shore of beautiful Town Cove in Orleans. This updated home has 3 bedrooms 2 1/2 baths Nicely appoi ...
From $726 per night (USD)
VRBO
From $494 per night (USD)
Expedia
WATER VIEWS! Eastham Getaway Awaits
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You and your family cannot beat the charm of this two bedroom house in Eastham. Water views out the sun room & ...
From $494 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Private Retreat for Families Yet Near Everything in Orleans!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
As you eagerly turn down the white shell driveway you will see this backlot property and instantly fall in love with thi ...
From $750 per night (USD)
VRBO
Click For Pricing
Expedia
Main House plus Guest House with Huge Yard, Walk to Nauset Beach!: 156-O
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties. Main House plus Guest House with Huge Yard, Walk to ...
Click For Pricing
Expedia
From $484 per night (USD)
VRBO
Private Lake Access, Great for Families!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: 15577 - Lakeside Retreat: Private Lake Access, Great for Families! The Space: Amidst the picturesque landscape ...
From $484 per night (USD)
VRBO
$NEW! Spacious Eastham Retreat, 3BD\/2BA, Bike Path, Dog-Friendly, Fenced Yard$
From $506 per night (USD)
VRBO
NEW! Spacious Eastham Retreat, 3BD\/2BA, Bike Path, Dog-Friendly, Fenced Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy tons of space in this IMMACULATE, bright open floorplan, with cathedral living room and FABULOUS kitchen. All new ...
From $506 per night (USD)
VRBO
From $3287 per night (USD)
VRBO
Upscale Vacation Estate with Pool Near Nauset Beach: 010-OB
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
This property is professionally managed by Pretty Picky Properties. Upscale Vacation Estate with Pool Near Nauset Beach ...
From $3287 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Exquisite New Renovation in Orleans: 063-O
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties. Exquisite New Renovation in Orleans Sleeps 6 3 Bed ...
From $313 per night (USD)
Expedia
From $719 per night (USD)
VRBO
The perfect spot to enjoy all that Orleans has to offer!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A perfect blend of old and new that exudes warmth and charm, the house is spacious and comfortable featuring 4 bedrooms ...
From $719 per night (USD)
VRBO
From $499 per night (USD)
VRBO
Newly Renovated Charming Beach Haven: 2-Minute Stroll to the Sand
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your seaside sanctuary! Nestled just a leisurely two-minute stroll from the pristine shores of the Bay, this ...
From $499 per night (USD)
VRBO
Click For Pricing
VRBO
Collins Cove Cottage 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This quintessential Cape Cod cottage is part of a popular cottage colony - only 7 cottages share a private sandy beach r ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Beachfront house with amazing views of the Atlantic Ocean and Nauset Inlet.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
The best views of anywhere on the Cape! Welcome to Nauset Heights. This comfortable and classic cottage has it all: a se ...
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Expedia
From $867 per night (USD)
VRBO
Home with water views, walking distance to restaurants, ice-cream, & shops
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This modern, recently renovated 3-bedroom, 3 full-bathroom home (with additional bonus area) sleeps up to 10 guest. Perf ...
From $867 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Short drive to town and popular beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 15578 - The Salty Hare: Short drive to town and popular beaches! The Space: Truly in the heart of Orleans and ...
From $533 per night (USD)
Expedia
Click For Pricing
VRBO
A Jewel of Nauset Heights With Saltwater Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
*Cancellation policy at end of property description.* This 3BR guest house has a charming rusticity with its exposed ...
Click For Pricing
VRBO
From $458 per night (USD)
Expedia
Walking distance to Orleans, stores and baseball games! Close to bay and ocean!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Stop searching for a cute place in Orleans that's close to everything, dog friendly, and meets your budget. You're alre ...
From $458 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Charming and newly updated one bedroom cottage centrally located in Eastham
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming one bedroom cottage, affectionately known as the Blueberry Cottage, is nestled in the Cottage Grove colon ...
From $268 per night (USD)
VRBO
$Eastham Studio w\/ Furnished Deck: 2 Mi to Beach!$
From $204 per night (USD)
Expedia
Eastham Studio w\/ Furnished Deck: 2 Mi to Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience a classic Cape Cod getaway at, ‘The Surf Shack,’ this lovely 1-bath studio cottage in Eastham, MA! With quick ...
From $204 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Newly renovated, close to beaches, Eastham studio cottage now available!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your stay in a newly acquired property with updated decor and kitchen. Start your day with coffee on the back dec ...
From $181 per night (USD)
VRBO
From $737 per night (USD)
Expedia
Brand New in Nauset Heights! 005-OD
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This home is professionally managed by Pretty Picky Properties. Brand New in Nauset Heights! Three Bedrooms, Two and ...
From $737 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Near Asa`s Landing | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bright, refreshed ranch convenient to Orleans center and 10 minutes to Nauset and Skaket beaches. Easy stroll to Town Co ...
From $442 per night (USD)
VRBO
From $710 per night (USD)
Expedia
Overlooking Nauset Beach | 5 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Located overlooking the sands of Nauset Beach, this spotless vacation home is a Cape Cod experience. Complete with 5 bed ...
From $710 per night (USD)
Expedia
From $1268 per night (USD)
VRBO
Waterfront Contemporary | 5 Bed, 4.5 Bath
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Waterfront Retreat with Scenic Water Views of Woods Cove, and Nauset Beach in Orleans to the Coast Guard Station in East ...
From $1268 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Cozy Cottage Overlooking | 1 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Orleans one bedroom bungalow in historic Rock Harbor. Immaculately restored with granite counters and beautiful har ...
From $383 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Historic Home in East Orleans | 3 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Listen to the waves in this historic home or walk to Nauset Beach! Home was once part of the Mayo Duck Farm and at one p ...
From $436 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Eastham Beach Haven | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This charming pet friendly 3 bedroom 2 bathroom home is spotless with upscale modern Cape Cod decor. Main level has full ...
From $413 per night (USD)
Expedia
From $544 per night (USD)
VRBO
Timeless Tonset Treasure | 4 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
5
Sleeps:
7
This quintessential Cape Cod home was built in 1775 and has been in the same family for almost 200 years. Charming beyon ...
From $544 per night (USD)
VRBO
Click For Pricing
Expedia
Westwind on Town Cove | 4 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Located right on the shore of beautiful Town Cove in Orleans. This family home has 4 bedrooms 2 baths and a view of the ...
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Expedia
From $641 per night (USD)
VRBO
Ocean Harbor Estates | 4 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beautiful 4 bedroom home located in Ocean Harbor Estates that offers tennis, footpath to saltwater association beach. A ...
From $641 per night (USD)
VRBO
From $1065 per night (USD)
Expedia
Stunning Waterfront | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Stunning cape contemporary style waterfront home with walls of glass and panoramic salt water views from most every room ...
From $1065 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Walk to Nauset Historic Home | 3 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile walk from beauti ...
From $436 per night (USD)
VRBO
Click For Pricing
Expedia
Path to Skaket Beach | 5 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Bea ...
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Expedia
From $369 per night (USD)
VRBO
Rock Harbor Beach Haven | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful split ranch is only .5 miles to Rock Harbor Beach and less than 1 mile to Cape Cod Rail Trail. Entry le ...
From $369 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Beautiful Cape Cod Summer Home | 3 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This 3 bedroom Cape Cod features a stunning new kitchen with white cabinetry, glass tile, new stainless appliances and l ...
From $692 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Stunning Cape Home Near Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This pet & family friendly newly renovated home in the heart of the Cape has 3 bedrooms, 2.5 baths, and sleeps 8, making ...
From $418 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Pochet Association Antique
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
STAY IN SOUGHT AFTER POCHET ASSOCIATION WITH PRIVATE ACCESS TO FOOTBRIDGE AND NAUSET BEACH. Feel like you were transfor ...
From $381 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Pet Friendly, Sleeps 4, Huge Back Yard, Skaket Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1.5 Bathrooms - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $319 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Charming, Modern, Comfortable 2BR Home in Orleans - With Premium Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the perfect blend of comfort and style in this beautifully updated home in Orleans, Massachusetts, one mile from N ...
From $361 per night (USD)
Expedia
From $740 per night (USD)
VRBO
Skaket Beach - Beachfront Property
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our bright, beautiful waterfront condo located directly on Skaket Beach. A perfect family vacation spot, yo ...
From $740 per night (USD)
VRBO
$BRAND NEW LISTING! 3BD+ Custom Home--A\/C, Hot Tub, Assoc. Dock & Beach, Town Cove Views$
From $1341 per night (USD)
VRBO
BRAND NEW LISTING! 3BD+ Custom Home--A\/C, Hot Tub, Assoc. Dock & Beach, Town Cove Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NEW TO THE RENTAL MARKET! Amazing sunrises over Town Cove! Beautiful Town Cove views and access from lovely, spacious h ...
From $1341 per night (USD)
VRBO
From $1021 per night (USD)
VRBO
East Orleans Waterfront Vacation Haven, Sleeps 10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Experience a quintessential Cape Cod vacation in Orleans at “One Particular Harbor”. This waterfront property boasts ame ...
From $1021 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Charming Guest House, with Waterviews & Private Beach! Perfect for Fun Weekends!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in South Orleans, this pet-friendly sun-filled Guest House offers 2 large bedrooms and 2 full baths. Located in ...
From $286 per night (USD)
Expedia

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Results: 460 Rentals