We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Orleans Holiday Rentals with Pools

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
216 rentals in Orleans.
Sort by:
Tripadvisor Sort
2 Greymoor Way 18282
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Orleans Lakefront Privacy, Lake Access, Tennis and Basketball Courts; 021-O
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Highly Rated Cottage in Orleans, Cape Cod
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
East Orleans - walk to Nauset Beach
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Walk to Crystal Lake; private Tennis Court; Basketball Hoop
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach
7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Quaint Cape Near Beaches And Centrally Located
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Orleans Pilgrim Lake Waterfront Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Home On Picturesque Pond Conveniently Located To Orleans And Chatham
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Orleans rentals sent straight to your email!
Sweeping Bay Views, Privacy, Two Kitchens: 071-O
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Enchanting Waterfront Escape on Pleasant Bay
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Booking now Summer 2021!
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Your perfect Cape Cod Getaway! Fully renovated cottage minutes from the beach!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
244 Tonset Road 125800
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Cozy studio cottage, walk to beach & dining - 300 yards to Nauset Beach!
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Your perch to the Cape's best ocean view with private Nauset access for 8!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
41 Pochet Rd 18558
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
5-BR Beach House Directly On Nauset Beach, Best Views on the East Coast 017-O
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Panoramic Views of the Atlantic
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
14 Iyanough Road 80840
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Waterfront,88 Tonset Road ID ***********
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
17 Center Place 18374
2 bedrooms
0 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Family-friendly, Colonial-style home complete w/ three-seasons patio & gas grill
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Walk to Nauset Beach $6,600wk, sleeps 8-10
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Serene, Riverside, Space to Spare, Access to Large Association Dock on Tidal Riv
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
SECLUDED NEW HOME ON LITTLE PLEASANT BAY WITH PRIVATE BEACH
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming, Renovated 1870s Home with Private Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Great cottage close to Nauset Beach, (linens included); 040-O
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
29 Greymoor Way 18520
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Main House 37244
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Unit #5 39659
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24
10 bedrooms
9 bathrooms
Sleeps 24
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Nauset Beach Home Sleeps 12+, 5 minute walk to beach, hot tub: 006-OR
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious five BR only 5 min to Nauset Beach with convenient Pochet Inlet access
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cozy Cape cottage w/ large backyard, deck & Ping-Pong - near golf/beaches!
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Rates lowered for the fall! Private Lux 8 BR Estate with Heated Pool!
8 bedrooms
9 bathrooms
Sleeps 22
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
#526: Luxury waterfront w/private sandy Beach. 9-seat movie theater - GAME ROOM!
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Walk to Skaket Beach
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cape Cod Charm walk to Arey's Pond
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
10 Cedar Land Road 40510
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
48 Nauset Road 22262
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Path to Skaket Beach
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Updated East Orleans 6 Bedroom Home with Heated Pool, linens incl. 004-O
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Superb Pleasant Bay Views, from Large, Luxurious, Secluded Orleans Vacation Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Orleans resort with water views, heated pool/spa & fire pit: 009-O
4 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stunning Carriage House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
12345