Orleans Vacation Rentals

1-42 of 70 rentals

USA Massachusetts Orleans

Dream in Orleans

$289 - $810 per night

3D Tour

4 Bed | 5 Bath | Sleeps 8

Nest on the Namequoit

$158 - $656 per night

3D Tour

4 Bed | 3 Bath | Sleeps 8

Beach Rose Guest Studio

$91 - $254 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

SeaWind Guest Studio

$91 - $254 per night

3D Tour

1 Bed | 1 Bath | Sleeps 3

Nauset Beach Dream

$92 - $344 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Nauset Beach Buddy

$88 - $295 per night

3D Tour

2 Bed | 1 Bath | Sleeps 4

Cranberry Lane Retreat

$200 - $359 per night

3D Tour

2 Bed | 2 Bath | Sleeps 7

The Harwich House

$128 - $453 per night

3D Tour

3 Bed | 1 Bath | Sleeps 6

Perfectly Provincetown

$99 - $475 per night

3D Tour

Provincetown, MA

1 Bed | 1 Bath | Sleeps 4

Bayside Retreat

$130 - $523 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 8

Monarch Haven

$174 - $579 per night

3D Tour

North Truro, MA

3 Bed | 1 Bath | Sleeps 6

South Chatham Sunshine

$124 - $773 per night

3D Tour

South Chatham, MA

3 Bed | 2 Bath | Sleeps 6

Meet Me at the Cape

$89 - $376 per night

3 Bed | 1 Bath | Sleeps 6

On The Water

$207 - $928 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 10

Chic Antique in Wellfleet Village

$124 - $616 per night

3D Tour

4 Bed | 3 Bath | Sleeps 10

Bayside Beauty

$102 - $443 per night

3D Tour

1 Bed | 1.5 Bath | Sleeps 5

Provincetown Dunes

$383 - $2,006 per night

3D Tour

Provincetown, MA

4 Bed | 3.5 Bath | Sleeps 8

The Waterfront Penthouse

$125 - $1,711 per night

3D Tour

Provincetown, MA

3 Bed | 2 Bath | Sleeps 6

Cape Escape

$89 - $400 per night

3D Tour

West Yarmouth, MA

3 Bed | 1.5 Bath | Sleeps 6

The Harbor Breeze

$133 - $464 per night

3D Tour

Provincetown, MA

2 Bed | 1 Bath | Sleeps 4

Provincetown Paradise

$88 - $396 per night

3D Tour

Provincetown, MA

0 Bed | 1 Bath | Sleeps 2

One Love - Eastham

$99 - $733 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 5

Hyannis Hideaway

$103 - $473 per night

3D Tour

3 Bed | 2 Bath | Sleeps 7 (5 Adults Max)

Harwich Port Perfection

$153 - $714 per night

3D Tour

3 Bed | 3.5 Bath | Sleeps 8

Bayside Cape Codder

$111 - $991 per night

3D Tour

3 Bed | 2 Bath | Sleeps 8

A Chatham Pearl on Oyster River

$108 - $683 per night

3D Tour

3 Bed | 2 Bath | Sleeps 6

Cerulean Cottage

$99 - $502 per night

3D Tour

2 Bed | 1 Bath | Sleeps 6

The Mary Alden

$200 - $535 per night

3D Tour

Provincetown, MA

2 Bed | 2 Bath | Sleeps 4

Cape Tip Townhouse

$128 - $725 per night

3D Tour

Provincetown, MA

3 Bed | 3.5 Bath | Sleeps 6

The Beauty of Brewster

$114 - $336 per night

3D Tour

4 Bed | 2.5 Bath | Sleeps 6

Bayview Cottage

$100 - $401 per night

3D Tour

West Yarmouth, MA

2 Bed | 1 Bath | Sleeps 6

Brewster Beaches

$150 - $286 per night

3D Tour

1 Bed | 2 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $918 per night

3D Tour

4 Bed | 2 Bath | Sleeps 8

Harwich Tranquility

$300 - $634 per night

3D Tour

3 Bed | 3 Bath | Sleeps 6

Sandpiper Hill Waterfront

$109 - $515 per night

3D Tour

3 Bed | 1.5 Bath | Sleeps 8

Escape in Dennis

$89 - $509 per night

3D Tour

3 Bed | 2 Bath | Sleeps 7

Welcome to Bob's Place

$121 - $387 per night

3D Tour

North Chatham, MA

2 Bed | 1 Bath | Sleeps 4

The Place to be...

$103 - $510 per night

3D Tour

Provincetown, MA

2 Bed | 1 Bath | Sleeps 5

Couple's Paradise by the Sea

$105 - $338 per night

3D Tour

1 Bed | 1 Bath | Sleeps 2

Seaside Cottage #1a - Seascape

$89 - $422 per night

3D Tour

South Yarmouth, MA

0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #11 - The Whale Watch

$89 - $419 per night

3D Tour

South Yarmouth, MA

0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #23a - Seagull's Nest

$107 - $506 per night

South Yarmouth, MA

2 Bed | 1 Bath | Sleeps 6

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About Orleans

Attractions

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

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