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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Place to stay in Wellfleet

4.98 out of 5 average rating, 163 reviews

WoodsideTiny House near Wellfleet Bay

Our tiny house tucked under trees is the perfect getaway. Walk past our orchard to get to your "Romantic Hideaway". This special rental has a private, sunny deck, a Nordic shower, stained glass windows and a library of books/vinyls. Set back from a quiet road on our property, this little gem is walking distance to Wellfleet's center, harbor & many restaurants, & just minutes drive from National Seashore beaches & ponds. A fun time in bustling Provincetown awaits you only 15 miles down the road!

Sep 19 – 26

$148 per night

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

May 17 – 24

$119 per night

Guest favorite

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 29 – May 6

$236 per night

Guest favorite

Condo in Brewster

4.87 out of 5 average rating, 162 reviews

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 Eaton village. One king bed and one queen, along with pullout couch allows 6 to sleep comfortably. 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!

Mar 24 – 31

$89 per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 541 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Mar 29 – Apr 5

$149 per night

Guest favorite

Apartment in East Orleans

4.94 out of 5 average rating, 258 reviews

Cozy Waterfront Apartment, Private Beach Access

Hello to all of my future guests. I want to wish you all well and safety in these uncertain times. I can assure you that this property is safe, private, spotless and affords you access to a beautiful private beach. I have updated the apartment to include a microwave and two kayaks. We are implicating extra sanitizing and cleaning measures to ensure the apartment is clean and safe for each guest! Please stay safe, optimistic, and let me know of any concerns. Sincerely, Patty

Jan 26 – Feb 2

$190 per night

Guest favorite

Apartment in Brewster

4.95 out of 5 average rating, 144 reviews

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

Dec 18 – 25

$122 per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 148 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Feb 2 – 9

$82 per night

Guest favorite

Apartment in Eastham

4.95 out of 5 average rating, 205 reviews

National Seashore Escape

There is no interaction required with hosts during stay. 1/4 mile to National Seashore Salt Pond Visitor Center and 2.0 miles to Coast Guard Beach, rated America's 6th best beach in 2019 by Dr Beach. The studio is above the garage with a private entrance private bath with shower. Queen bed, wifi, whisper quiet mini split a/c no window unit, tv. There is a kitchenette with refrigerator, microwave, coffee maker, toaster, sink, no stove.

Sep 2 – 7

$155 per night

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 226 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

May 2 – 9

$114 per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 142 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Oct 1 – 8

$113 per night

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 342 reviews

Barn Cottage on Minister Pond

Newly renovated cozy heated Barn Cottage (not attached to house- privacy!) on Minister Pond with dock access to canoe/ new queen size bed/equipped kitchen/large deck overlooking pond/gas grill/private yard/2 minutes to ocean or bay beaches and bike trail in National Seashore/ many local attractions, and restaurants! Please note the new 12.45% short term rental tax is now in effect and will be added to your base. Thank you

Oct 20 – 27

$125 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orleans vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Orleans's top sights

Wequassett Resort and Golf Club59 locals recommend

Hot Chocolate Sparrow58 locals recommend

the knack51 locals recommend

Land Ho85 locals recommend

Hole In One Breakfast & Lunch47 locals recommend

Christmas Tree Shops27 locals recommend

Other great vacation rentals in Orleans

Guest favorite

Home in Chatham

4.96 out of 5 average rating, 191 reviews

Studio cottage in Chatham Ma.

Mar 4 – 11

$149 per night

Guest favorite

Home in Brewster

4.95 out of 5 average rating, 137 reviews

Brewster Home on Lower Mill Pond

Feb 28 – Mar 7

$145 per night

Superhost

Home in Chatham

4.82 out of 5 average rating, 135 reviews

Delightful Chatham Cottage, Cheerful and Clean

May 27 – Jun 3

$137 per night

Guest favorite

Home in North Truro

4.98 out of 5 average rating, 262 reviews

Beautiful North Truro cottage with screen porch

Jan 7 – 14

$139 per night

Guest favorite

Home in Chatham

4.95 out of 5 average rating, 238 reviews

Slate House - a modern waterfront getaway

Mar 18 – 25

$373 per night

Guest favorite

Home in Eastham

4.97 out of 5 average rating, 163 reviews

The Sea Captain's Carriage House

Jan 12 – 19

$244 per night

Guest favorite

Home in Chatham

5.0 out of 5 average rating, 123 reviews

Chatham Charmer

Feb 12 – 19

$220 per night

Superhost

Home in Dennis

4.84 out of 5 average rating, 134 reviews

Cozy Centrally Located 3BR Cottage

Nov 12 – 19

$100 per night

Show all

Orleans beach vacation rentals

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 278 reviews

In-town, Pied-a-Terre. Private, Sunny Comfy Home.

Dec 5 – 12

$145 per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

Sep 3 – 10

$108 per night

Guest favorite

Apartment in Eastham

4.88 out of 5 average rating, 244 reviews

Cape Cod Suite Near Private Beach

Mar 27 – Apr 3

$135 per night

Guest favorite

Cottage in Eastham

4.96 out of 5 average rating, 152 reviews

Cozy 2 bedroom cottage steps from Moll's Pond

Aug 24 – 31

$305 per night

Guest favorite

Condo in Dennis

4.84 out of 5 average rating, 164 reviews

The 5 minute walk to beach Super Cute Beach Condo

Sep 15 – 22

$121 per night

Guest favorite

Cottage in Eastham

4.95 out of 5 average rating, 204 reviews

The Breeze Overlooking Minister's Pond

Aug 24 – 31

$376 per night

Guest favorite

Guest suite in Wellfleet

4.95 out of 5 average rating, 170 reviews

Wellfleet Get Away

Aug 28 – Sep 4

$181 per night

Guest favorite

Cottage in Eastham

4.99 out of 5 average rating, 181 reviews

The Salt Pond Cottage

Aug 26 – Sep 2

$225 per night

Show all

Orleans cottage rentals

Guest favorite

Cottage in Dennis Port

4.9 out of 5 average rating, 145 reviews

Cape Cod Cottage 3/4 Mile from the Beach

Jan 11 – 18

$92 per night

Guest favorite

Cottage in East Orleans

4.95 out of 5 average rating, 107 reviews

Distiller’s Cottage Nauset Beach East Orleans, MA

Jan 31 – Feb 7

$260 per night

Superhost

Cottage in Dennis

4.88 out of 5 average rating, 348 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Mar 23 – 30

$175 per night

Guest favorite

Cottage in Wareham

4.97 out of 5 average rating, 261 reviews

Cottage on Sunset Cove

Mar 18 – 25

$118 per night

Guest favorite

Cottage in Chatham

4.96 out of 5 average rating, 214 reviews

Cozy Cottage

Oct 3 – 10

$203 per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 102 reviews

Steps to the Beach Kid Friendly

May 7 – 14

$249 per night

Guest favorite

Cottage in Harwichport

4.94 out of 5 average rating, 295 reviews

Newly renovated Cape Coddage! Location! Location!

Nov 5 – 12

$471 per night

Guest favorite

Cottage in Provincetown

4.9 out of 5 average rating, 275 reviews

Freestanding Studio Cottage West End

May 2 – 9

$119 per night

Show all

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
9.2K 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 730 vacation rentals in East Orleans, and over 310 vacation rentals in South 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 40 cottage rentals to over 300 house 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 120 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.

Orleans vacation rentals

Top-rated vacation rentals in Orleans

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Orleans vacation rentals

Stay near Orleans's top sights

Other great vacation rentals in Orleans

Home in Chatham

Home in Brewster

Home in Chatham

Home in North Truro

Home in Chatham

Home in Eastham

Home in Chatham

Home in Dennis

Orleans beach vacation rentals

Condo in Chatham

Cottage in Bourne

Apartment in Eastham

Cottage in Eastham

Condo in Dennis

Cottage in Eastham

Guest suite in Wellfleet

Cottage in Eastham

Orleans cottage rentals

Cottage in Dennis Port

Cottage in East Orleans

Cottage in Dennis

Cottage in Wareham

Cottage in Chatham

Cottage in Dennis

Cottage in Harwichport

Cottage in Provincetown

Quick stats about vacation rentals in Orleans

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Orleans?

What types of vacation rentals are available in Orleans?

Are there vacation rentals with a dedicated workspace in Orleans?

Are there pet-friendly vacation rentals in Orleans?

Do house rentals in Orleans have a gym?

Are there Orleans house rentals on Airbnb with pools?

Do house rentals in Orleans have a bbq area?

Do house rentals in Orleans have self check-in?

Do house rentals in Orleans have wifi?

Are there family-friendly house rentals in Orleans?

Destinations to explore