South Orleans Vacation Rentals

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Vacation Rentals in South Orleans

🐚The Bay Cottage on Thumpertown Beach
9.8 out of 10, Exceptional, (11)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
$338 nightly
The price is $387
Oct 27 - Oct 28
Total with taxes and fees
🐚The Bay Cottage on Thumpertown Beach
Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (117)
"Super clean and a really large space! "
United States
Linda
$157 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
Brewster Green Resort
Edgewood on Campground Beach/Steps to the Sand
10.0 out of 10, Exceptional, (9)
"Wonderful location and lovely stay at the cottage. Would book again!"
United States
MelanieC
$376 nightly
The price is $431
Oct 27 - Oct 28
Total with taxes and fees
Edgewood on Campground Beach/Steps to the Sand
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.6 out of 10, Exceptional, (29)
"Great visit! Clean property a bit tucked in the woods but overall close to everything and a great spot for the price!"
United States
Christian B.
$303 nightly
The price is $347
Nov 2 - Nov 3
Total with taxes and fees
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
10.0 out of 10, Exceptional, (24)
"Very nice house and neighborhood. We enjoyed our stay very much and hope to return next year!"
United States
Lisa D.
$562 nightly
The price is $643
Nov 19 - Nov 20
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
9.6 out of 10, Exceptional, (99)
"Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. "
United States
Mike D.
$358 nightly
The price is $409
Oct 27 - Oct 28
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Captain's Quarters by Nauset Beach
10.0 out of 10, Exceptional, (6)
"Cape Cod cottage close to the beach."
United States
Bill B.
$484 nightly
The price is $554
Oct 27 - Oct 28
Total with taxes and fees
Captain's Quarters by Nauset Beach
The Breeze on Minister's Pond
10.0 out of 10, Exceptional, (25)
"We had a lovely time at the Breeze for a few days away from NYC. Tara was a great host and provided us with everything we needed so we had more time to relax and enjoy the area. Will definitely be back to explore the area more!"
United States
Jackson v.
$339 nightly
The price is $388
Oct 28 - Oct 29
Total with taxes and fees
The Breeze on Minister's Pond
Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach
10.0 out of 10, Exceptional, (28)
"We had a wonderful time and great weather!!!"
United States
Peter C.
Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach
🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
$377 nightly
The price is $432
Oct 27 - Oct 28
Total with taxes and fees
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Stylish 2nd floor Ocean Edge condo
9.8 out of 10, Exceptional, (9)
"Fine clean quiet place to spend the night."
United States
Frederick K.
$353 nightly
The price is $404
Oct 27 - Oct 28
Total with taxes and fees
Stylish 2nd floor Ocean Edge condo
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
$441 nightly
The price is $505
Oct 27 - Oct 28
Total with taxes and fees
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Seaside Getaway - Harwichport Beachhouse
9.8 out of 10, Exceptional, (9)
"Great location great property"
United States
Glenn M.
$320 nightly
The price is $366
Oct 28 - Oct 29
Total with taxes and fees
Seaside Getaway - Harwichport Beachhouse
Holly Tree Resort
3.0 star property
9.0 out of 10, Wonderful, (359)
"We had a great stay!"
United States
Shelly
Holly Tree Resort
Cozy Large Home in Harwich with Patio near Wequassett Resort
9.8 out of 10, Exceptional, (11)
"We had a great time here - the kids’ room is truly special!"
Canada
Aravind
$514 nightly
The price is $569
Nov 16 - Nov 17
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$339 nightly
The price is $375
Nov 3 - Nov 4
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
10.0 out of 10, Exceptional, (2)
"Cosy retreat with pond view. Great for canoeing with the dog. Sweet porch for reading and morning coffee. Tara was an excellent host who communicated immediately and went well above and beyond to correct an issue that was out of her control.A great central location that allowed us to roam freely to our favorite beaches, hikes, and restaurants. We will gladly return in the future. "
United States
Anne P.
$340 nightly
The price is $390
Oct 30 - Oct 31
Total with taxes and fees
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Sand Bar-Dog Friendly on Cooks Brook Beach
10.0 out of 10, Exceptional, (20)
"The house was comfortable and proximity to the beach was great. Hosts were attentive and friendly. Thanks for a great stay"
United States
M G.
$426 nightly
The price is $488
Oct 27 - Oct 28
Total with taxes and fees
Sand Bar-Dog Friendly on Cooks Brook Beach
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 out of 10, Exceptional, (20)
"Lovely property, spacious and VERY clean..location is ideal..."
United States
Kathy M.
$446 nightly
The price is $511
Oct 28 - Oct 29
Total with taxes and fees
The Pet-Friendly Surf Shack Hideaway on the Cove
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
10.0 out of 10, Exceptional, (74)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
$423 nightly
The price is $484
Nov 11 - Nov 12
Total with taxes and fees
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Orleans Hotel Reviews

Find out more about South Orleans

Everything you need to know about South Orleans vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Orleans vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Orleans vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Orleans vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Orleans. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Orleans in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Orleans rentals

At Expedia, we put the best South Orleans vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Orleans rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Orleans vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Orleans. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in South Orleans?

Yes, we offer vacation rentals close to popular sights in South Orleans, or you can go with a more remote option if you're looking for a relaxing stay. South Orleans is known for its seafood restaurants and beaches. Make sure you have time to check out the local tours while you're in the area.

What are some of the best vacation rentals that South Orleans has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This vacation home rental near South Orleans is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in South Orleans?

With 31 Expedia vacation rentals, you're sure to find just the right place for your South Orleans stay.

What’s there to see and do in South Orleans?

Explore the area and family-friendly sights such as West Dennis Beach, or get out into nature at a spot like Cape Cod Beaches. In the larger area, you’ll find Nickerson State Park and Skaket Beach.

What’s a vacation rental in South Orleans like?

Vacation rentals are private accommodations you can stay in for several days or longer in South Orleans. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips.