Orleans vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Orleans

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

Guest favorite
Condo in Brewster
Shining Sea Condo
Ocean Edge condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within the Eaton village. Two queen beds along with pullout couch allows 6 to sleep comfortably within the unit. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!
Jan 19 – 26Individual Host,
€ 113 per night
4.86 out of 5 average rating, 152 reviews
Guest favorite
Cottage in Orleans
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!
Nov 13 – 20Individual Host,
€ 326 per night
4.93 out of 5 average rating, 128 reviews
Guest favorite
Home in Chatham
Delightful Chatham Cottage, Cheerful and Clean
AirBnB Superhost, local owner has 20 years of online vacation rental experience with this property. Recently refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at a very affordable price. Enjoy a relaxing stay while being close to everything in town.
Apr 14 – 21
€ 144 per night
4.82 out of 5 average rating, 134 reviews

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

Orleans house rentals

Guest favorite
Home in Brewster
Brewster Home on Lower Mill Pond
Dec 11 – 18
€ 188 per night
4.95 out of 5 average rating, 136 reviews
Guest favorite
Home in Chatham
Studio cottage in Chatham Ma.
Feb 2 – 9
€ 196 per night
4.96 out of 5 average rating, 189 reviews
Guest favorite
Home in Eastham
The Sea Captain's Carriage House
Nov 13 – 20Individual Host,
€ 318 per night
4.97 out of 5 average rating, 163 reviews
Guest favorite
Home in Brewster
The Drake Cottage - Brewster Beach Getaway
Apr 18 – 25Individual Host,
€ 176 per night
4.83 out of 5 average rating, 163 reviews
Guest favorite
Home in Brewster
Cozy Cape Cabin - just minutes to Cape Cod Bay!
Apr 25 – May 2Individual Host,
€ 208 per night
4.92 out of 5 average rating, 134 reviews
Guest favorite
Home in Chatham
Chatham Charmer
Feb 17 – 24
€ 282 per night
5.0 out of 5 average rating, 122 reviews
Guest favorite
Home in Chatham
Slate House - a modern waterfront getaway
Aug 30 – Sep 6Individual Host,
€ 1,029 per night
4.96 out of 5 average rating, 234 reviews
Guest favorite
Home in Brewster
Perfect Cape Cod vacation home
Apr 10 – 17
€ 276 per night
4.99 out of 5 average rating, 102 reviews
Guest favorite
Home in Chatham
Close to everything in Chatham
Dec 10 – 17Individual Host,
€ 369 per night
4.97 out of 5 average rating, 108 reviews
Guest favorite
Home in Eastham
Bayside Bliss
Nov 28 – Dec 5Individual Host,
€ 377 per night
4.99 out of 5 average rating, 134 reviews
Guest favorite
Home in Harwich
cape cod riverview cottage
May 8 – 15Individual Host,
€ 377 per night
4.98 out of 5 average rating, 494 reviews
Guest favorite
Home in Brewster
Shop, Swim, Hike, Bike in Historic Brewster
Jan 20 – 27Individual Host,
€ 233 per night
4.93 out of 5 average rating, 102 reviews

Orleans beach vacation rentals

Guest favorite
Condo in Chatham
Stroll to town, private, sunny condo.
Nov 3 – 10Individual Host,
€ 193 per night
4.96 out of 5 average rating, 275 reviews
Guest favorite
Condo in Dennis
Studio, 300 yards to Glendon, Mermaid Haven #1
Oct 16 – 23Individual Host,
€ 142 per night
4.96 out of 5 average rating, 144 reviews
Guest favorite
Cottage in Bourne
140 Steps to Beach. Cottage with views
Feb 2 – 9
€ 145 per night
5.0 out of 5 average rating, 143 reviews
Guest favorite
Cottage in Eastham
The Salt Pond Cottage
Apr 1 – 8Individual Host,
€ 211 per night
4.99 out of 5 average rating, 179 reviews
Guest favorite
Apartment in Eastham
Cape Cod Suite Near Private Beach
Jan 2 – 9
€ 177 per night
4.88 out of 5 average rating, 244 reviews
Guest favorite
Cottage in Chatham
Forbes, a South Chatham cottage
Nov 7 – 14Individual Host,
€ 180 per night
4.9 out of 5 average rating, 124 reviews
Guest favorite
Apartment in Eastham
King bed/Hot Tub/Waterfront-The Lotus
Jun 7 – 14Individual Host,
€ 565 per night
4.93 out of 5 average rating, 168 reviews
Guest favorite
Guest suite in Chatham
The Captain Kimball House of Christmas Joy
Nov 10 – 17Individual Host,
€ 245 per night
4.94 out of 5 average rating, 140 reviews
Guest favorite
Cottage in Dennis
Walk to Beach - Experience Dennis Beach House - AC
Oct 15 – 22
€ 213 per night
4.94 out of 5 average rating, 212 reviews
Guest favorite
Cottage in Harwichport
Newly renovated Cape Coddage! Location! Location!
Feb 25 – Mar 4Individual Host,
€ 617 per night
4.93 out of 5 average rating, 289 reviews
Guest favorite
Apartment in Harwich
Cozy Apartment in Downtown Harwich Port
Nov 23 – 30Individual Host,
€ 248 per night
4.98 out of 5 average rating, 167 reviews
Guest favorite
Cabin in Brewster
Cozy Cape Cabin
May 8 – 15Individual Host,
€ 153 per night
4.98 out of 5 average rating, 58 reviews

Orleans cottage rentals

Guest favorite
Cottage in Dennis Port
Cape Cod Cottage 3/4 Mile from the Beach
Dec 19 – 26Professional Host,
€ 136 per night
4.9 out of 5 average rating, 145 reviews
Guest favorite
Cottage in Chatham
Cozy Cottage
Apr 19 – 26Individual Host,
€ 243 per night
4.96 out of 5 average rating, 212 reviews
Superhost
Cottage in Dennis
Waterfront Cottage on White Pond(Graham Cracker)
Feb 12 – 19Individual Host,
€ 232 per night
4.88 out of 5 average rating, 345 reviews
Guest favorite
Cottage in Wellfleet
Hillside Cottage
Nov 21 – 28Individual Host,
€ 301 per night
4.93 out of 5 average rating, 234 reviews
Superhost
Cottage in Yarmouth
Cozy Cottage near Bay beaches great for a couple!
May 2 – 9Individual Host,
€ 120 per night
4.85 out of 5 average rating, 177 reviews
Guest favorite
Cottage in Dennis
The Strandloper / Beachwalker Cottage
Sep 7 – 14Professional Host,
€ 246 per night
4.95 out of 5 average rating, 191 reviews
Guest favorite
Cottage in Wellfleet
The Perfect Getaway in Wellfleet
Sep 16 – 23
€ 281 per night
4.9 out of 5 average rating, 248 reviews
Guest favorite
Cottage in Chatham
Cape Cod Classic Cottage Near Forest Beach
Jan 30 – Feb 6Individual Host,
€ 380 per night
4.94 out of 5 average rating, 141 reviews
Guest favorite
Cottage in Dennis
3 Redwing Place- walk to beach and tennis!
Apr 19 – 26Individual Host,
€ 223 per night
4.97 out of 5 average rating, 211 reviews
Guest favorite
Cottage in Yarmouth
Cozy Coastal Cottage With Sprawling Sea Views
Oct 4 – 11Individual Host,
€ 210 per night
4.95 out of 5 average rating, 177 reviews
Guest favorite
Cottage in Dennis
Steps to the Beach Kid Friendly
May 27 – Jun 3Individual Host,
€ 384 per night
4.94 out of 5 average rating, 101 reviews
Guest favorite
Cottage in Wellfleet
The Perfect Cape Retreat
Apr 18 – 25
€ 238 per night
4.94 out of 5 average rating, 143 reviews

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

Frequently Asked Questions

  • Where should I stay in Orleans?

    Make yourself at home in Orleans by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in South Orleans, and over 740 vacation rentals in East Orleans.

  • What types of vacation rentals are available in Orleans?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Orleans. From over 310 house rentals to over 30 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Orleans?

    Yes! Work meets play with ease at over 130 vacation rentals in Orleans featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Orleans?

    Four-legged friends are welcome in Orleans. Choose from more than 130 vacation rentals for guests traveling with pets.

  • Do house rentals in Orleans have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there Orleans house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Orleans, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Orleans have a bbq area?

    Absolutely! We offer over 190 house rentals with a bbq area in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orleans have self check-in?

    Absolutely! We offer over 130 house rentals with self check-in in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orleans have wifi?

    Absolutely! We offer over 300 house rentals with wifi in Orleans. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Orleans?

    Orleans has more than 280 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore