Orleans Vacation Rentals

1-38 of 38 rentals

USA Massachusetts Orleans

Orleans Oasis

$136 - $535 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nest on the Namequoit

$114 - $789 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Nauset Beach Buddy

$64 - $267 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

SeaWind Guest Studio

$50 - $224 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Nauset Beach Dream

$89 - $335 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Beach Rose Guest Studio

$49 - $231 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Mazi's Cottage

$131 - $446 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Eastham Escape

$72 - $485 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Bayside Retreat

$64 - $352 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

Cranberry Classic

$89 - $369 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

One Love - Eastham

$99 - $423 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Whale Song

$89 - $528 per night

3 Bed | 1 Bath | Sleeps 6

Hideaway Near The Bay

$64 - $386 per night

2 Bed | 1.5 Bath | Sleeps 4

Eastham Cottage

$79 - $214 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Easy Eastham

$89 - $383 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

North Eastham Shores

$139 - $683 per night

3D Tour

5 Bed | 2 Bath | Sleeps 12

Pine Grove Cottage

$80 - $273 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Cerulean Cottage

$81 - $271 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Rail Trail Cottage

$103 - $411 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$109 - $275 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $306 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Brewster Serenity

$114 - $578 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Welcome to Bob's Place

$120 - $385 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

A Chatham Pearl on Oyster River

$89 - $643 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Couple's Paradise by the Sea

$49 - $325 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

On The Water

$140 - $284 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 10

It's a Keeper

$114 - $599 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Lucky Number Seven

$138 - $402 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $707 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$89 - $523 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Harwich Port Perfection

$89 - $670 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Harwich Tranquility

$300 - $646 per night

3D Tour

3 Bed | 3 Bath | Sleeps 6

Big Pine Cottage

$100 - $284 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

The Harwich House

$150 - $428 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Port Cottage

$64 - $289 per night

3D Tour

Harwich Port, MA

2 Bed | 1 Bath | Sleeps 5

Chic Antique in Wellfleet Village

$124 - $537 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Sandpiper Hill Waterfront

$99 - $697 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 8

Starfish Getaway

$64 - $289 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

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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