South Orleans Holiday Rentals

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Holiday Rentals in South Orleans

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"Super clean and a really large space! "
United States
Linda
The price is NZ$312
includes taxes & fees
20 Nov - 21 Nov
Brewster Green Resort

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
West Brewster
10.0 out of 10, Exceptional, (24)
"The house was very clean and comfortable. The outdoor patio is especially nice as well."
United States
Gina C.
The price is NZ$1,100
includes taxes & fees
20 Nov - 21 Nov
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is NZ$602
includes taxes & fees
1 Dec - 2 Dec
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
9.6 out of 10, Exceptional, (100)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$733
includes taxes & fees
30 Nov - 1 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

National Seashore/Updated/Game Room~Blue Pearl

Eastham
10.0 out of 10, Exceptional, (8)
" We enjoyed our stay at the property. We loved the location. My only issue is two little things. First, the ppropettypropermanager is"
United States
Richard M.
The price is NZ$874
includes taxes & fees
20 Nov - 21 Nov
National Seashore/Updated/Game Room~Blue Pearl

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham
9.6 out of 10, Exceptional, (4)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is NZ$896
includes taxes & fees
20 Nov - 21 Nov
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham
10.0 out of 10, Exceptional, (115)
"Comfortable and terrific location"
United States
Barry L.
The price is NZ$869
includes taxes & fees
20 Nov - 21 Nov
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
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.
The price is NZ$769
includes taxes & fees
1 Dec - 2 Dec
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Seaside Getaway - Harwichport Beachhouse

Harwich
9.8 out of 10, Exceptional, (9)
"Great location great property"
United States
Glenn M.
The price is NZ$713
includes taxes & fees
20 Nov - 21 Nov
Seaside Getaway - Harwichport Beachhouse

The Cove At Yarmouth

3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is NZ$227
includes taxes & fees
30 Nov - 1 Dec
The Cove At Yarmouth

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Chatham
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.
The price is NZ$553
includes taxes & fees
1 Dec - 2 Dec
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

The Alpine/Walk to Beach for 2 or more!

Eastham
9.2 out of 10, Wonderful, (11)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is NZ$951
includes taxes & fees
2 Dec - 3 Dec
The Alpine/Walk to Beach for 2 or more!

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Eastham
10.0 out of 10, Exceptional, (18)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is NZ$884
includes taxes & fees
2 Dec - 3 Dec
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Pond House~Waterfront Oasis W/Jacuzzi Tub

Eastham
10.0 out of 10, Exceptional, (10)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is NZ$898
includes taxes & fees
20 Nov - 21 Nov
Pond House~Waterfront Oasis W/Jacuzzi Tub

New! Island Pines-A Dog Friendly Boutique Oasis

Wellfleet
9.4 out of 10, Exceptional, (11)
"Property is beautiful, in a lovely setting, private but not too far from activities and great food. The house is maintained well and was perfectly clean, with a few maintenance issues which could be corrected quickly (bathroom doors that do not close and an extraordinarily squeaky upper floor.)"
United States
Marshal G.
The price is NZ$994
includes taxes & fees
20 Nov - 21 Nov
New! Island Pines-A Dog Friendly Boutique Oasis

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is NZ$281
includes taxes & fees
21 Nov - 22 Nov
Secluded-Entire 2nd floor Suite with Private Bath

The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham
10.0 out of 10, Exceptional, (21)
"Lovely property, spacious and VERY clean..location is ideal..."
United States
Kathy M.
The price is NZ$885
includes taxes & fees
20 Nov - 21 Nov
The Pet-Friendly Surf Shack Hideaway on the Cove

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Brewster
10.0 out of 10, Exceptional, (41)
"My son was playing in Massachusetts Open Golf Tournament- location and property were perfect. - definitely visit again. "
United States
Sal S.
The price is NZ$606
includes taxes & fees
20 Nov - 21 Nov
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich
9.8 out of 10, Exceptional, (11)
"We had a great time here - the kids’ room is truly special!"
Canada
Aravind
The price is NZ$923
includes taxes & fees
7 Dec - 8 Dec
Cozy Large Home in Harwich with Patio near Wequassett Resort

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham
10.0 out of 10, Exceptional, (23)
"We had the most wonderful week at the Sandbar. The check in/out process was flawless. The location is ideal. The sunsets were magnificent. Would definitely recommend. "
United States
Holly M.
The price is NZ$857
includes taxes & fees
23 Nov - 24 Nov
Sand Bar-Dog Friendly on Cooks Brook Beach
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Orleans holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Orleans holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Orleans holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Orleans holiday rentals we have selected for you start as low as NZ$312 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Orleans rentals

At Expedia, we put the best South Orleans holiday 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 holiday.

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 holiday rental in South Orleans?

Yes, there are holiday rentals close to the most popular sights in South Orleans, or you can select a more secluded 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 holiday rentals that South Orleans has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This holiday home rental outside of South Orleans is located in the city centre, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in South Orleans?

With 34 Expedia holiday rentals, you're guaranteed 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 Cape Cod Lavender Farm, or get out into nature at a spot like Cape Cod Beaches. In the wider area, you’ll find Nickerson State Park and Skaket Beach.

What’s a holiday rental in South Orleans like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Orleans. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.