Vacation rentals in Orleans

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Top-rated vacation rentals in Orleans

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Guest favorite

Place to stay in Wellfleet

4.97 out of 5 average rating, 168 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!

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!!!

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!

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 545 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.

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a Private Association Beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal. Close to restaurants, hiking trails, and Mass Maritime. Last Min May-10% off, 3,4,5 day 10% off.

Guest favorite

Apartment in East Orleans

4.94 out of 5 average rating, 260 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

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.

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 153 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.

Guest favorite

Apartment in Eastham

4.95 out of 5 average rating, 207 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.

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 227 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.

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.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orleans vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

National Seashore8 locals recommend

Land Ho85 locals recommend

Other great vacation rentals in Orleans

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 279 reviews

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

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 344 reviews

Barn Cottage on Minister Pond

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 189 reviews

Classic Cape Cod Cottage

Guest favorite

Condo in Dennis

4.84 out of 5 average rating, 166 reviews

The 5 minute walk to beach Super Cute Beach Condo

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 120 reviews

Modern Luxury Apt. | 7 min from Commons

Guest favorite

Cottage in East Orleans

4.95 out of 5 average rating, 107 reviews

Distiller’s Cottage Nauset Beach East Orleans, MA

Guest favorite

Guest suite in Chatham

4.99 out of 5 average rating, 203 reviews

Waterfront Suite on Emery Pond

Guest favorite

Home in Brewster

4.95 out of 5 average rating, 140 reviews

Brewster Home on Lower Mill Pond

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

What are the most popular amenities for Cottage Rentals in Orleans?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with a bbq area, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Orleans?
Orleans has more than 340 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
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 vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Orleans, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in bed and breakfast rentals in Orleans?
Experience the best of Orleans with our bed and breakfast rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Orleans have a bbq area?
Absolutely! We offer over 20 cabin rentals with a bbq area in Orleans. Enjoy a tailored experience with all the comforts you desire.
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.
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 apartment rentals in Orleans have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Orleans. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Orleans

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

Condo in Chatham

Cottage in Eastham

Cottage in Eastham

Condo in Dennis

Apartment in Falmouth

Cottage in East Orleans

Guest suite in Chatham

Home in Brewster

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

What are the most popular amenities for Cottage Rentals in Orleans?

Are there family-friendly vacation rentals in Orleans?

Are there vacation rentals with a dedicated workspace in Orleans?

Do house rentals in Orleans have a gym?

Are there Orleans vacation rentals on Airbnb with pools?

How much does it cost to stay in bed and breakfast rentals in Orleans?

Do cabin rentals in Orleans have a bbq area?

Where should I stay in Orleans?

Do house rentals in Orleans have self check-in?

Do apartment rentals in Orleans have wifi?

Destinations to explore