Orleans Vacation Rentals

1-42 of 92 rentals
USA Massachusetts Orleans

Dream in Orleans

$254 - $841  per night
3D Tour
4 Bed | 5 Bath | Sleeps 8

Orleans Oasis

$160 - $618  per night
3D Tour
4 Bed | 2 Bath | Sleeps 9

Nauset Beach Buddy

$81 - $383  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Nest on the Namequoit

$114 - $943  per night
3D Tour
4 Bed | 3 Bath | Sleeps 8

Beach Rose Guest Studio

$91 - $331  per night
3D Tour
1 Bed | 1 Bath | Sleeps 3

SeaWind Guest Studio

$56 - $331  per night
3D Tour
1 Bed | 1 Bath | Sleeps 3

Cranberry Lane Retreat

$200 - $486  per night
3D Tour
2 Bed | 2 Bath | Sleeps 7

Nauset Beach Dream

$99 - $481  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

Bayside Retreat

$64 - $401  per night
3D Tour
2 Bed | 1 Bath | Sleeps 5

Easy Eastham

$89 - $443  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Whale Song

$89 - $583  per night
3 Bed | 1 Bath | Sleeps 6

Pine Grove Cottage

$64 - $365  per night
2 Bed | 1 Bath | Sleeps 4

One Love - Eastham

$99 - $522  per night
3D Tour
3 Bed | 1.5 Bath | Sleeps 5

Eastham Escape

$72 - $476  per night
3D Tour
2 Bed | 1 Bath | Sleeps 8

Cerulean Cottage

$64 - $445  per night
3D Tour
2 Bed | 1 Bath | Sleeps 6

North Eastham Shores

$268 - $1,633  per night
NEW!
5 Bed | 2 Bath | Sleeps 12

Hideaway Near The Bay

$70 - $482  per night
2 Bed | 1.5 Bath | Sleeps 4

Brewster Serenity

$114 - $718  per night
3D Tour
4 Bed | 2 Bath | Sleeps 8

Brewster Beaches

$150 - $391  per night
3D Tour
1 Bed | 2 Bath | Sleeps 6

Welcome to Bob's Place

$64 - $520  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

On The Water

$222 - $837  per night
3D Tour
4 Bed | 2.5 Bath | Sleeps 10

A Chatham Pearl on Oyster River

$89 - $874  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Couple's Paradise by the Sea

$51 - $430  per night
3D Tour
1 Bed | 1 Bath | Sleeps 2

The Sea Chest in The South of Chatham

$300 - $1,123  per night
3D Tour
4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$89 - $734  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Harwich Port Perfection

$89 - $810  per night
3D Tour
3 Bed | 3.5 Bath | Sleeps 8

The Harwich House

$89 - $519  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

Big Pine Cottage

$64 - $368  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Harwich Tranquility

$300 - $634  per night
3D Tour
3 Bed | 3 Bath | Sleeps 6

Port Cottage

$113 - $383  per night
NEW!
2 Bed | 1 Bath | Sleeps 5

Chic Antique in Wellfleet Village

$129 - $975  per night
3D Tour
4 Bed | 3 Bath | Sleeps 10

Sandpiper Hill Waterfront

$144 - $1,015  per night
3D Tour
3 Bed | 1.5 Bath | Sleeps 8

Sweet Home

$166 - $659  per night
NEW!
4 Bed | 1.5 Bath | Sleeps 8

Bayside Cape Codder

$89 - $1,225  per night
3D Tour
3 Bed | 2 Bath | Sleeps 8

Sandpiper's Saltbox

$114 - $1,021  per night
3D Tour
4 Bed | 2 Bath | Sleeps 8

Escape in Dennis

$89 - $622  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7

Cape Cod Bliss

$153 - $2,253  per night
3D Tour
4 Bed | 3.5 Bath | Sleeps 8

Dennis Port Delight

$250 - $584  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7

Seaside Cottage #1 - Coastal Haven

$98 - $432  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #16 Beach Cottage

$121 - $458  per night
0 Bed | 1 Bath | Sleeps 3

Seaside Cottage #21 - The Chesapeake

$128 - $484  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #35 - The Bird House

$128 - $484  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4 (3 Adults Max)
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About Orleans
Attractions

Discover the small-town charm, beautiful beaches, and convenient location of lovely Orleans on Cape Cod. Our collection of Orleans vacation rentals provide the perfect home base to explore the entire Cape Cod National Seashore! 

Photo credit: Lynne Albright via Shutterstock

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