Southeast Massachusetts Holiday Rentals

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Holiday Rentals in Southeast Massachusetts

Sandcastle Resort and Club
3.0 star property
7.4 out of 10, Good, (1122)
"Right on the beach, outstanding room/views"
The price is AU$172
includes taxes & fees
19 Oct - 20 Oct
Sandcastle Resort and Club
Edgewater Beach Resort, a VRI resort
3.5 star property
8.8 out of 10, Excellent, (287)
"All around a great place to stay!"
The price is AU$271
includes taxes & fees
23 Oct - 24 Oct
Edgewater Beach Resort, a VRI resort
Modern Beachfront Condo, Gorgeous Views and Centrally Located
10.0 out of 10, Exceptional, (56)
"Great property have stayed multiple times. Had a concern and John handled it immediately. Great host and great location. Will book again soon. "
Modern Beachfront Condo, Gorgeous Views and Centrally Located
Holly Tree Resort
3.0 star property
9.0 out of 10, Wonderful, (358)
"Nice rooms nice property great location"
Holly Tree Resort
Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (113)
"Nice big space. "
The price is AU$367
includes taxes & fees
20 Oct - 21 Oct
Brewster Green Resort
Riverview Resort
3.0 star property
9.2 out of 10, Wonderful, (166)
"The room was big and very clean. The hotel is quaint and quiet. It does not have an elevator which could be an issue for some but we made it work. Overall a great place to stay. Very comfortable and inviting and we loved the amenities."
The price is AU$311
includes taxes & fees
2 Nov - 3 Nov
Riverview Resort
The Cove at Yarmouth by VRI Americas
3.5 star property
9.2 out of 10, Wonderful, (322)
"spacious, clean, loved the townhouse suite, convenient location"
The price is AU$439
includes taxes & fees
21 Oct - 22 Oct
The Cove at Yarmouth by VRI Americas
InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (187)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 out of 10, Exceptional, (26)
"Heaven! Best spot on the end of cul de sac with stunning water views from all rooms, especially the outdoor deck. Clean, comfortable and nicely decorated. Great communication pre check-in and during stay. Did not want to leave! Look forward to future stay. "
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
10.0 out of 10, Exceptional, (285)
"Perfect for a couple!Everything was amazing."
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (228)
"Wonderful stay. Cottage is very clean and the location can’t be beat. Will be back. "
Steps to the Ocean! Perfect Location!!!
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
10.0 out of 10, Exceptional, (172)
"Great place to stay! Walking distance to town and lovely yard to relax in."
The price is AU$1,204
includes taxes & fees
17 Oct - 18 Oct
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Thomas Sea Suites
3.5 star property
9.0 out of 10, Wonderful, (90)
"Excellent "
Thomas Sea Suites
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
10.0 out of 10, Exceptional, (38)
"I can’t say enough good things about this property! Beautifully decorated, well stocked kitchen, plenty of beach and pool towels, excellent location, tons of space for everyone to spread out, activities for kids, everyone had their own bathroom, helpful host - you can’t ask for anything more! Definitely the nicest property we ever stayed at!"
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
9.4 out of 10, Exceptional, (41)
"We stayed at 8 Atlantic Avenue for the Daffodil Festival weekend. The home is impeccable and beautiful - spacious with gorgeous hardwood floors and a kitchen meant for entertaining. Close to town for shopping and restaurants. Owners were a pleasure to work with and I would highly recommend this property! We loved every aspect of our stay and will definitely rent there again."
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
Steps to a private beach in a classic Cape cottage. Pet-friendly!
8.8 out of 10, Excellent, (27)
"We had a great week. Location was perfect, steps from the beach. "
Steps to a private beach in a classic Cape cottage. Pet-friendly!
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
8.8 out of 10, Excellent, (80)
"3rd time staying at the rental and we really enjoyed as always! "
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Cape Cod Bay Home w/ Deck + Private Beach Access
9.6 out of 10, Exceptional, (34)
"Stunning house! Beautifully appointed"
Cape Cod Bay Home w/ Deck + Private Beach Access
Harbourtown Suites
4.0 star property
9.2 out of 10, Wonderful, (69)
"Great location great staff extremely clean highly Recommend. I can’t wait to go back next summer !"
The price is AU$710
includes taxes & fees
18 Oct - 19 Oct
Harbourtown Suites
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 Southeast Massachusetts Hotel Reviews

Find out more about Southeast Massachusetts

Everything you need to know about Southeast Massachusetts 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 Southeast Massachusetts 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 Southeast Massachusetts holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southeast Massachusetts holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southeast Massachusetts. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southeast Massachusetts 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 Southeast Massachusetts holiday rentals we have selected for you start as low as AU$172 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southeast Massachusetts rentals

At Expedia, we put the best Southeast Massachusetts 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 Southeast Massachusetts 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 Southeast Massachusetts 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 Southeast Massachusetts. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.