Orleans Vacation Rentals

1-42 of 55 rentals

USA Massachusetts Orleans

Paradise On Cape Cod

$124 - $672 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 8

Pine Point

$114 - $465 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Nest on the Namequoit

$114 - $730 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Nauset Beach Dream

$89 - $423 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

SeaWind Guest Studio

$49 - $299 per night

3D Tour

0 Bed | 1 Bath | Sleeps 3

Beach Rose Guest Studio

$49 - $299 per night

3D Tour

0 Bed | 1 Bath | Sleeps 3

Nauset Beach Buddy

$64 - $377 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Orleans Oasis

$114 - $568 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Hideaway Near The Bay

$77 - $423 per night

3D Tour

2 Bed | 1.5 Bath | Sleeps 4

Sandy Forest

$168 - $593 per night

3D Tour

3 Bed | 2.5 Bath | Sleeps 9

Beaches n' Sunsets

$155 - $969 per night

3 Bed | 2 Bath | Sleeps 9

Bayside Retreat

$69 - $405 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

One Love - Eastham

$74 - $448 per night

3D Tour

2 Bed | 1.5 Bath | Sleeps 5

Villa on the Water

$500 - $746 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 6

Whale Song

$94 - $176 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Eastham Escape

$95 - $380 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Go Coastal

$79 - $256 per night

3D Tour

0 Bed | 1 Bath | Sleeps 2

Pine Grove Cottage

$120 - $120 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Gateway to the Cape

$159 - $457 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Mazi's Cottage

$208 - $560 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Easy Eastham

$152 - $438 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Northwood Nest

$187 - $367 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Nan's Beach House

$300 - $300 per night

3D Tour

North Eastham, MA

2 Bed | 1 Bath | Sleeps 6

Paradise by the Bay

$183 - $621 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

The Grounds

$144 - $376 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Edge Retreat

$110 - $222 per night

3D Tour

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

Ocean Mandevilla

$120 - $345 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Ocean Isle

$250 - $467 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Relaxing Cape Getaway

$92 - $334 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$184 - $691 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Brewster Beaches

$150 - $345 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

Welcome to Bob's Place

$158 - $474 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

Bike the Beach

$114 - $585 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Summer Lovin'

$114 - $941 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Lucky Number Seven

$98 - $531 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

A Chatham Pearl on Oyster River

$89 - $768 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

B By the Sea

$102 - $559 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Couple's Paradise by the Sea

$105 - $370 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

It's a Keeper

$219 - $470 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

The Sea Chest in The South of Chatham

$300 - $500 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$89 - $729 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

The Harwich House

$150 - $492 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