Orleans Vacation Rentals

1-42 of 53 rentals

USA Massachusetts Orleans

Pine Point

$128 - $416 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Nest on the Namequoit

$131 - $598 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

SeaWind Guest Studio

$86 - $268 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Paradise On Cape Cod

$168 - $612 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 8

Beach Rose Guest Studio

$86 - $268 per night

3D Tour

0 Bed | 1 Bath | Sleeps 3

Orleans Oasis

$164 - $509 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nauset Beach Dream

$113 - $423 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Nauset Beach Buddy

$90 - $336 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Beaches n' Sunsets

$94 - $749 per night

3 Bed | 2 Bath | Sleeps 9

Eastham Escape

$109 - $404 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Bayside Retreat

$74 - $431 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

Easy Eastham

$116 - $466 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Hideaway Near The Bay

$98 - $450 per night

2 Bed | 1.5 Bath | Sleeps 4

Go Coastal

$72 - $271 per night

3D Tour

0 Bed | 1 Bath | Sleeps 2

Whale Song

$106 - $476 per night

3 Bed | 1 Bath | Sleeps 6

One Love - Eastham

$99 - $476 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Pine Grove Cottage

$78 - $138 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Northwood Nest

$150 - $428 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Villa on the Water

$500 - $676 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 6

Mazi's Cottage

$144 - $536 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Nan's Beach House

$166 - $588 per night

3D Tour

North Eastham, MA

2 Bed | 1 Bath | Sleeps 6

The Grounds

$142 - $543 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$100 - $258 per night

3D Tour

1 Bed | 2 Bath | Sleeps 5 (4 Adults Max)

Ocean Mandevilla

$116 - $395 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $406 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$167 - $868 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Welcome to Bob's Place

$139 - $450 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Jons Landing

$156 - $593 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

It's a Keeper

$181 - $631 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Couple's Paradise by the Sea

$129 - $333 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

A Chatham Pearl on Oyster River

$124 - $589 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

B. by Sea

$134 - $451 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Lucky Number Seven

$134 - $432 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $838 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Chatham Tranquility

$272 - $448 per night

4 Bed | 2 Bath | Sleeps 10

South Chatham Sunshine

$162 - $655 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Harwich Roses

$130 - $578 per night

2 Bed | 1 Bath | Sleeps 6

Sea la Vie

$96 - $265 per night

2 Bed | 1 Bath | Sleeps 4

The Harwich House

$150 - $625 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Harwich Tranquility

$250 - $692 per night

3D Tour

3 Bed | 3 Bath | Sleeps 6

Big Pine Cottage

$100 - $409 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Beach Happy

$135 - $606 per night

3D Tour

Harwich Port, MA

3 Bed | 2 Bath | Sleeps 6

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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