Orleans Vacation Rentals

1-42 of 46 rentals

USA Massachusetts Orleans

SeaWind Guest Studio

$96 - $323 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Pine Point

$128 - $583 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Beach Rose Guest Studio

$98 - $334 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Nauset Beach Dream

$108 - $511 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Nauset Beach Buddy

$86 - $406 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Orleans Oasis

$147 - $605 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nest on the Namequoit

$134 - $898 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Easy Eastham

$103 - $483 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Northwood Nest

$74 - $483 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Swell Escape

$89 - $483 per night

3D Tour

3 Bed | 1 Bath | Sleeps 7

Eastham Escape

$72 - $483 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Hideaway Near The Bay

$64 - $502 per night

2 Bed | 1.5 Bath | Sleeps 4

One Love - Eastham

$99 - $533 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Eastham Cottage

$49 - $282 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Whale Song

$89 - $685 per night

3 Bed | 1 Bath | Sleeps 6

Pine Grove Cottage

$82 - $372 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Mazi's Cottage

$111 - $594 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

North Eastham Shores

$424 - $1,712 per night

3D Tour

5 Bed | 2 Bath | Sleeps 12

Ocean Mandevilla

$99 - $453 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $410 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Rail Trail Cottage

$132 - $537 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$145 - $233 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$192 - $889 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Welcome to Bob's Place

$120 - $443 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Fantastic Chatham Family Home

$139 - $1,644 per night

3D Tour

5 Bed | 4.5 Bath | Sleeps 12

Couple's Paradise by the Sea

$91 - $433 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Jons Landing

$132 - $790 per night

3D Tour

3 Bed | 2 Bath | Sleeps 9

It's a Keeper

$142 - $690 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

A Chatham Pearl on Oyster River

$89 - $858 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Lucky Number Seven

$95 - $536 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $1,135 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$143 - $753 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Harwich Roses

$142 - $482 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 - $574 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Big Pine Cottage

$104 - $380 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

The Spray

$64 - $383 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

Port Cottage

$64 - $388 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

Wellfleet Woods

$178 - $685 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Chic Antique in Wellfleet Village

$124 - $785 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

School House

$158 - $250 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Tree Top Oasis

$189 - $1,001 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 12

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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