Vacation rentals in Orleans

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Orleans

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guest suite in Chatham

4.94 out of 5 average rating, 140 reviews

The Captain Kimball House of Christmas Joy

Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.

May 3 – 10

$238 CAD per night
Guest favourite

Condo in Chatham

4.96 out of 5 average rating, 277 reviews

In-town, Pied-a-Terre. Private, Sunny condo.

Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Dec. 14 – 21

$279 CAD per night
Guest favourite

Cottage in Orleans

4.93 out of 5 average rating, 128 reviews

Cape Cod Cottage with view of Orleans Town Cove

The cottage is very clean, cute and comfortable and has every thing you might need. Situated in a quiet, friendly little neighborhood, right next to the famous Cottage Street Bakery, yet you would never know you are so close to town! It is centrally located within walking distance to restaurants, shops and bike path, with the Ice Cream Cafe right down the street on the corner. 3 miles to all beaches. Access to the Cove including kayak rental is just down the street. Perfect location!

Apr. 12 – 19

$481 CAD per night

Popular amenities for Orleans vacation rentals

Stay near Orleans's top sights

Wequassett Resort and Golf Club59 locals recommend
Hot Chocolate Sparrow58 locals recommend
Cape Escape Adventure Golf25 locals recommend
the knack51 locals recommend
Land Ho85 locals recommend
Hole In One Breakfast & Lunch47 locals recommend

Other great vacation rentals in Orleans

Guest favourite

Condo in Dennis

4.96 out of 5 average rating, 144 reviews

Studio, 300 yards to Glendon, Mermaid Haven #1

Oct. 14 – 21

$208 CAD per night
Guest favourite

Home in Chatham

4.96 out of 5 average rating, 189 reviews

Studio cottage in Chatham Ma.

Nov. 23 – 30

$289 CAD per night
Guest favourite

Cottage in Eastham

4.95 out of 5 average rating, 204 reviews

The Breeze Overlooking Minister's Pond

Apr. 18 – 25

$330 CAD per night
Guest favourite

Cottage in East Orleans

4.95 out of 5 average rating, 107 reviews

Distiller’s Cottage Nauset Beach East Orleans, MA

Sep. 8 – 15

$471 CAD per night
Guest favourite

Tiny homes in Wellfleet

4.98 out of 5 average rating, 226 reviews

Writer's Cabin in Woods near Wellfleet Bay

Jun. 8 – 15

$278 CAD per night
Guest favourite

Home in Brewster

4.95 out of 5 average rating, 137 reviews

Brewster Home on Lower Mill Pond

Feb. 25 – Mar. 4

$277 CAD per night
Guest favourite

Apartment in Eastham

4.88 out of 5 average rating, 244 reviews

Cape Cod Suite Near Private Beach

Nov. 13 – 20

$261 CAD per night
Guest favourite

Cottage in Orleans

4.98 out of 5 average rating, 59 reviews

Hobbit Cottage with Marsh View

Nov. 12 – 19

$266 CAD per night
Guest favourite

Guest suite in Orleans

4.95 out of 5 average rating, 79 reviews

Spacious Guest Suite Close to Town

Apr. 11 – 18

$221 CAD per night
Guest favourite

Cabin in Brewster

4.98 out of 5 average rating, 58 reviews

Cozy Cape Cabin

May 8 – 15

$225 CAD per night
Guest favourite

Guest suite in Eastham

4.99 out of 5 average rating, 97 reviews

Beautiful Cape Cod location - Bay, Ocean, and Pond

May 12 – 19

$188 CAD per night
Guest favourite

Home in Orleans

4.96 out of 5 average rating, 25 reviews

Gorgeous Renovation Walk to Water!

Oct. 21 – 28

$815 CAD per night

Quick stats about vacation rentals in Orleans

Total rentals

410 properties

Rentals with dedicated workspaces

130 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

130 properties allow pets

Family-friendly rentals

340 properties are a good fit for families

Total number of reviews

9.8K reviews

Destinations to explore