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Orleans Luxury Vacation Rentals

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334 rentals in Orleans.
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Charming Post & Beam Near State Park and Pond
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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East Orleans - walk to Nauset Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Highly Rated Cottage in Orleans, Cape Cod
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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The private back yard is dominated by a dramatic 60 ft. oblong swimming pool
This very tall contemporary colonial style home spans 4 floors of living space
A view of the beach on Pleasant Bay at low tide, a 1/2 mile walk.
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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5 BR/4 bath w/heated pool .2 miles to Nauset Beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Quaint Cape Near Beaches And Centrally Located
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Save time - get the best Orleans rentals sent straight to your email!
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 8 Bedroom Home w/ Pool - 4 minutes to the beach!
Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Stunning Ocean Front Luxury Home on Nauset Beach with A/C & WiFi
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 16
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Your perfect Cape Cod Getaway! Fully renovated cottage minutes from the beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Booking now Summer 2021!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Salty Dog Cottage In East Orleans With Access To Town Cove
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
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Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Walk to Skaket Beach
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
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#502: COMPLETELY Renovated, Walk to Water & Preservation Land!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Your perch to the Cape's best ocean view with private Nauset access for 8!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Quaint & Immaculate on Town Cove in East Orleans
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Spacious Orleans Apartment With Private Beach Access
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Central AC, Spacious, 5-level, beautiful home, near lakes and beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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41 Pochet Rd 18558
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Charming Cottage w/ Deck - Walk to Skaket Beach!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Enchanting Waterfront Summer Escape on Pleasant Bay
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 7
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Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
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Delightfully Located Home Near Scenic Pah Wah Pond
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Romantic Orleans Waterfront Cottage!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24
Holiday Rental House
10 bedrooms
11 bathrooms
Sleeps 24
Match: Sleeps
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#505: Walk to Nauset Beach! Private yard & large private patio!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront- E Orleans! Panoramic Views, Dock, Central Air, Kayaks, Walk to Shop
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Family-Friendly Home On Beach Rd. Close To Nauset Beach & Village Ctr.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Discounted Beach Home: June 18-July 8
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Orleans resort-style compound: heated pool/spa, fire pit & cabana 023-O
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Stunning East Orleans Residence 2 Miles from Nauset Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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