Orleans Vacation Rentals

1-40 of 40 rentals

USA Massachusetts Orleans

Nest on the Namequoit

$114 - $1,007 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Pine Point

$140 - $626 per night

3D Tour

4 Bed | 2 Bath | Sleeps 7

Orleans Oasis

$114 - $659 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nauset Beach Dream

$101 - $450 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

SeaWind Guest Studio

$98 - $297 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Beach Rose Guest Studio

$103 - $295 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Nauset Beach Buddy

$88 - $358 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Cranberry Classic

$89 - $568 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Bayside Retreat

$64 - $549 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

One Love - Eastham

$99 - $453 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Eastham Cottage

$49 - $312 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Mazi's Cottage

$64 - $664 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Easy Eastham

$103 - $375 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

North Eastham Shores

$521 - $990 per night

3D Tour

5 Bed | 2 Bath | Sleeps 12

Eastham Escape

$72 - $542 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Pine Grove Cottage

$88 - $422 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Cerulean Cottage

$174 - $298 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Whale Song

$89 - $780 per night

3 Bed | 1 Bath | Sleeps 6

Hideaway Near The Bay

$64 - $566 per night

2 Bed | 1.5 Bath | Sleeps 4

Ocean Mandevilla

$144 - $361 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Ocean Edge Retreat

$168 - $259 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Rail Trail Cottage

$145 - $435 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Brewster Beaches

$150 - $330 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Welcome to Bob's Place

$120 - $453 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Fantastic Chatham Family Home

$303 - $1,221 per night

3D Tour

5 Bed | 4.5 Bath | Sleeps 12

A Chatham Pearl on Oyster River

$89 - $717 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

It's a Keeper

$152 - $648 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Couple's Paradise by the Sea

$100 - $363 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Lucky Number Seven

$130 - $449 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $797 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$89 - $535 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

The Harwich House

$150 - $479 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Harwich Tranquility

$250 - $634 per night

3D Tour

3 Bed | 3 Bath | Sleeps 6

Big Pine Cottage

$123 - $235 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Port Cottage

$64 - $327 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

The Spray

$101 - $320 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

Chic Antique in Wellfleet Village

$124 - $855 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Wellfleet Woods

$180 - $633 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Starfish Getaway

$83 - $370 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Sandpiper Hill Waterfront

$114 - $879 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 8

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About Orleans

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