Orleans Vacation Rentals

1-42 of 53 rentals

USA Massachusetts Orleans

Pine Point

$133 - $428 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Nest on the Namequoit

$137 - $618 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Paradise On Cape Cod

$166 - $624 per night

3D Tour

4 Bed | 3.5 Bath | Sleeps 8

SeaWind Guest Studio

$89 - $276 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Beach Rose Guest Studio

$89 - $276 per night

3D Tour

0 Bed | 1 Bath | Sleeps 3

Orleans Oasis

$168 - $523 per night

3D Tour

4 Bed | 2 Bath | Sleeps 9

Nauset Beach Dream

$117 - $436 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Nauset Beach Buddy

$93 - $347 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Gateway to the Cape

$126 - $483 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Eastham Escape

$106 - $413 per night

3D Tour

2 Bed | 1 Bath | Sleeps 8

Beaches n' Sunsets

$164 - $949 per night

3 Bed | 2 Bath | Sleeps 9

Bayside Retreat

$71 - $407 per night

3D Tour

2 Bed | 1 Bath | Sleeps 5

One Love - Eastham

$99 - $450 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Hideaway Near The Bay

$95 - $440 per night

2 Bed | 1.5 Bath | Sleeps 4

Go Coastal

$72 - $279 per night

3D Tour

0 Bed | 1 Bath | Sleeps 2

Pine Grove Cottage

$74 - $221 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Whale Song

$102 - $245 per night

3 Bed | 1 Bath | Sleeps 6

Northwood Nest

$150 - $423 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Villa on the Water

$500 - $752 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 6

Easy Eastham

$116 - $467 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Mazi's Cottage

$188 - $547 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Nan's Beach House

$157 - $555 per night

3D Tour

North Eastham, MA

2 Bed | 1 Bath | Sleeps 6

Paradise by the Bay

$207 - $728 per night

3D Tour

3 Bed | 2 Bath | Sleeps 10

Ocean Edge Retreat

$113 - $230 per night

3D Tour

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

The Grounds

$143 - $508 per night

3D Tour

2 Bed | 2 Bath | Sleeps 4

Ocean Mandevilla

$117 - $374 per night

3D Tour

2 Bed | 2 Bath | Sleeps 6

Brewster Beaches

$150 - $370 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Beauty of Brewster

$160 - $744 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Welcome to Bob's Place

$154 - $511 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

A Chatham Pearl on Oyster River

$137 - $738 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Lucky Number Seven

$132 - $502 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

Couple's Paradise by the Sea

$132 - $377 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

B By the Sea

$194 - $320 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Chatham Tranquility

$263 - $461 per night

4 Bed | 2 Bath | Sleeps 10

It's a Keeper

$212 - $655 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

The Sea Chest in The South of Chatham

$300 - $496 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

South Chatham Sunshine

$160 - $741 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Harwich Roses

$135 - $433 per night

2 Bed | 1 Bath | Sleeps 6

Sea la Vie

$97 - $274 per night

2 Bed | 1 Bath | Sleeps 4

The Harwich House

$150 - $513 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Big Pine Cottage

$100 - $349 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Harwich Tranquility

$250 - $561 per night

3D Tour

3 Bed | 3 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