Orleans vacation rentals

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Top-rated vacation rentals in Orleans

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

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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

G$35,325 GYD 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!!!

Oct 12 – 19

G$26,185 GYD per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 543 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.

Nov 26 – Dec 3

G$31,968 GYD per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 116 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Oct 25 – Nov 1

G$14,621 GYD 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

Sep 30 – Oct 7

G$45,520 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 150 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.

Dec 14 – 21

G$19,858 GYD 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 18 – 23

G$35,688 GYD 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.

Nov 26 – Dec 3

G$27,312 GYD per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 143 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 3 – 10

G$27,061 GYD 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

Nov 22 – 29

G$29,887 GYD per night

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 188 reviews

Classic Cape Cod Cottage

15 min walk to the best bayside beach. Very peaceful setting. Four night minimum stay from April 15 to June 15. June 15 to Sept 10 there's a 7 night minimum stay, from Saturday to Saturday. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore.

Oct 30 – Nov 6

G$33,309 GYD per night

Guest favorite

Guest suite in Orleans

4.99 out of 5 average rating, 205 reviews

Private Beach, Cozy Cape Cottage

Enjoy your own private beach with soaring seabirds and ocean breeze! Let a breathtaking sunrise and view of the bay greet you every morning from bed. Take in the waterfront view on the outside patio by the garden or in the enclosed sun porch. Escape to our cozy cottage secluded in the woods with nearby trails. Explore the Cape's many attractions and refresh your soul with a relaxing Cape Cod vacation.

Sep 26 – Oct 3

G$59,291 GYD 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

National Seashore8 locals recommend

Land Ho85 locals recommend

Hole In One Breakfast & Lunch47 locals recommend

Other great vacation rentals in Orleans

Guest favorite

Home in Chatham

4.96 out of 5 average rating, 192 reviews

Studio cottage in Chatham Ma.

Mar 10 – 17

G$35,811 GYD per night

Guest favorite

Home in North Truro

4.98 out of 5 average rating, 264 reviews

Beautiful North Truro cottage with screen porch

Jan 27 – Feb 3

G$33,139 GYD per night

Guest favorite

Home in Brewster

4.95 out of 5 average rating, 138 reviews

Brewster Home on Lower Mill Pond

Mar 13 – 20

G$34,724 GYD per night

Guest favorite

Home in Chatham

4.95 out of 5 average rating, 240 reviews

Slate House - a modern waterfront getaway

Nov 10 – 17

G$99,998 GYD per night

Guest favorite

Home in Chatham

5.0 out of 5 average rating, 123 reviews

Chatham Charmer

Mar 15 – 22

G$52,763 GYD per night

Guest favorite

Home in Eastham

4.97 out of 5 average rating, 163 reviews

The Sea Captain's Carriage House

Jun 12 – 19

G$61,045 GYD per night

Guest favorite

Home in Brewster

4.92 out of 5 average rating, 135 reviews

Cozy Cape Cabin - just minutes to Cape Cod Bay!

Oct 26 – Nov 2

G$40,786 GYD per night

Guest favorite

Home in Truro

4.88 out of 5 average rating, 171 reviews

Cape Cod Getaway 2 Bedroom Cozy Home

Nov 1 – 8

G$32,981 GYD per night

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Orleans beach vacation rentals

Guest favorite

Cottage in Orleans

4.93 out of 5 average rating, 128 reviews

Cape Cod Cottage with view of Orleans Town Cove

May 14 – 21

G$60,111 GYD per night

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 279 reviews

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

Nov 16 – 23

G$35,705 GYD 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

May 8 – 15

G$47,025 GYD 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

Dec 27 – Jan 3

G$30,055 GYD per night

Guest favorite

Apartment in Eastham

4.88 out of 5 average rating, 244 reviews

Cape Cod Suite Near Private Beach

Oct 2 – 9

G$32,476 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 216 reviews

Walk to Beach - Experience Dennis Beach House - AC

Nov 30 – Dec 7

G$36,319 GYD per night

Guest favorite

Cottage in Eastham

4.95 out of 5 average rating, 206 reviews

The Breeze Overlooking Minister's Pond

Oct 8 – 15

G$55,234 GYD per night

Guest favorite

Cottage in Eastham

4.99 out of 5 average rating, 181 reviews

The Salt Pond Cottage

Jul 26 – Aug 2

G$53,847 GYD per night

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Orleans cottage rentals

Guest favorite

Cottage in Chatham

4.96 out of 5 average rating, 214 reviews

Cozy Cottage

Oct 13 – 20

G$48,179 GYD 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

Oct 4 – 11

G$62,184 GYD per night

Superhost

Cottage in Dennis

4.88 out of 5 average rating, 350 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Feb 6 – 13

G$42,161 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 102 reviews

Steps to the Beach Kid Friendly

Jun 4 – 11

G$75,743 GYD per night

Guest favorite

Cottage in Dennis

4.95 out of 5 average rating, 191 reviews

The Strandloper / Beachwalker Cottage

Dec 16 – 23

G$42,052 GYD per night

Guest favorite

Cottage in Harwichport

4.94 out of 5 average rating, 299 reviews

Newly renovated Cape Coddage! Location! Location!

Nov 5 – 12

G$112,412 GYD per night

Guest favorite

Cottage in Yarmouth

4.95 out of 5 average rating, 177 reviews

Cozy Coastal Cottage With Sprawling Sea Views

Oct 17 – 24

G$38,728 GYD per night

Guest favorite

Cottage in Provincetown

4.9 out of 5 average rating, 275 reviews

Freestanding Studio Cottage West End

May 17 – 24

G$31,860 GYD per night

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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 300 house rentals to over 40 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 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

Cottages

Houses

Hotels

Popular amenities for Orleans vacation rentals

Stay near Orleans's top sights

Other great vacation rentals in Orleans

Home in Chatham

Home in North Truro

Home in Brewster

Home in Chatham

Home in Chatham

Home in Eastham

Home in Brewster

Home in Truro

Orleans beach vacation rentals

Cottage in Orleans

Condo in Chatham

Cottage in Eastham

Condo in Dennis

Apartment in Eastham

Cottage in Dennis

Cottage in Eastham

Cottage in Eastham

Orleans cottage rentals

Cottage in Chatham

Cottage in East Orleans

Cottage in Dennis

Cottage in Dennis

Cottage in Dennis

Cottage in Harwichport

Cottage in Yarmouth

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