Orleans Vacation Rentals

1-42 of 46 rentals

USA Massachusetts Orleans

Pine Point

$130 - $554 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

SeaWind Guest Studio

$96 - $307 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Beach Rose Guest Studio

$98 - $318 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Nauset Beach Dream

$108 - $484 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Nauset Beach Buddy

$86 - $385 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Orleans Oasis

$147 - $575 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nest on the Namequoit

$134 - $843 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Northwood Nest

$74 - $479 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Easy Eastham

$103 - $479 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Swell Escape

$89 - $479 per night

3D Tour

3 Bed | 1 Bath | Sleeps 7

Eastham Escape

$72 - $479 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

One Love - Eastham

$99 - $527 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Hideaway Near The Bay

$64 - $497 per night

2 Bed | 1.5 Bath | Sleeps 4

Eastham Cottage

$49 - $280 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Whale Song

$89 - $678 per night

3 Bed | 1 Bath | Sleeps 6

Pine Grove Cottage

$82 - $368 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Mazi's Cottage

$111 - $589 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

North Eastham Shores

$428 - $1,694 per night

3D Tour

5 Bed | 2 Bath | Sleeps 12

Ocean Mandevilla

$99 - $449 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $406 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Rail Trail Cottage

$132 - $532 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$142 - $235 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$191 - $878 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Welcome to Bob's Place

$120 - $441 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Jons Landing

$132 - $793 per night

3D Tour

3 Bed | 2 Bath | Sleeps 9

Fantastic Chatham Family Home

$271 - $1,648 per night

3D Tour

5 Bed | 4.5 Bath | Sleeps 12

It's a Keeper

$142 - $686 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

A Chatham Pearl on Oyster River

$89 - $861 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Couple's Paradise by the Sea

$91 - $434 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Lucky Number Seven

$95 - $538 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $1,140 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$143 - $756 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Harwich Roses

$142 - $486 per night

2 Bed | 1 Bath | Sleeps 6

Harwich Tranquility

$250 - $634 per night

3D Tour

3 Bed | 3 Bath | Sleeps 6

The Harwich House

$150 - $580 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Big Pine Cottage

$104 - $384 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Port Cottage

$64 - $392 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

The Spray

$108 - $384 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

Wellfleet Woods

$182 - $704 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

School House

$161 - $250 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Tree Top Oasis

$184 - $981 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 12

Chic Antique in Wellfleet Village

$124 - $809 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

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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