Orleans Vacation Rentals

1-42 of 56 rentals

USA Massachusetts Orleans

Paradise On Cape Cod

$124 - $842 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 8

Pine Point

$114 - $583 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Nauset Beach Buddy

$73 - $406 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Nauset Beach Dream

$115 - $511 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

SeaWind Guest Studio

$91 - $323 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Beach Rose Guest Studio

$95 - $334 per night

3D Tour

0 Bed | 1 Bath | Sleeps 3

Nest on the Namequoit

$134 - $898 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Orleans Oasis

$165 - $605 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Mazi's Cottage

$149 - $606 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Swell Escape

$135 - $552 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Villa on the Water

$89 - $779 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 6

Northwood Nest

$74 - $493 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Go Coastal

$49 - $309 per night

3D Tour

0 Bed | 1 Bath | Sleeps 2

Easy Eastham

$89 - $528 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Eastham Escape

$72 - $493 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

One Love - Eastham

$99 - $545 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Bayside Retreat

$64 - $494 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

Whale Song

$89 - $701 per night

3 Bed | 1 Bath | Sleeps 6

Hideaway Near The Bay

$64 - $513 per night

2 Bed | 1.5 Bath | Sleeps 4

Pine Grove Cottage

$80 - $210 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Eastham Cottage

$49 - $266 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

North Eastham Shores

$402 - $1,751 per night

3D Tour

5 Bed | 2 Bath | Sleeps 12

Nan's Beach House

$110 - $672 per night

3D Tour

North Eastham, MA

2 Bed | 1 Bath | Sleeps 6

Fieldstone at Ocean Edge

$131 - $749 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

Rail Trail Cottage

$132 - $549 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$81 - $350 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Ocean Mandevilla

$99 - $462 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $420 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$139 - $916 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Welcome to Bob's Place

$120 - $470 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Chatham Tranquility

$154 - $874 per night

4 Bed | 2 Bath | Sleeps 10

Couple's Paradise by the Sea

$72 - $434 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

It's a Keeper

$114 - $733 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Fantastic Chatham Family Home

$223 - $1,648 per night

3D Tour

5 Bed | 4.5 Bath | Sleeps 12

Jons Landing

$99 - $857 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

A Chatham Pearl on Oyster River

$89 - $861 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

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

$120 - $756 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Sea la Vie

$87 - $380 per night

2 Bed | 1 Bath | Sleeps 4

Harwich Roses

$88 - $481 per night

2 Bed | 1 Bath | Sleeps 6

The Harwich House

$150 - $573 per night

3D Tour

3 Bed | 1 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