Southeast Massachusetts Holiday Rentals

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Holiday Rentals in Southeast Massachusetts

Sandcastle Resort and Club

3.0 star property
Provincetown
7.4 out of 10, Good, (1141)
"Very nice place in front of the beach, beautiful view whole year round ☀️🌊"
United States
Maria
The price is NZ$200
includes taxes & fees
11 Nov - 12 Nov
Sandcastle Resort and Club

Edgewater Beach Resort, a VRI resort

3.5 star property
Dennis Port
8.8 out of 10, Excellent, (290)
"All around a great place to stay!"
United States
Samantha
Edgewater Beach Resort, a VRI resort

Holly Tree Resort

3.0 star property
West Yarmouth
9.0 out of 10, Wonderful, (363)
"Yearly trip that makes it all worth it with our stay at the Holly Tree!"
United States
Angel
Holly Tree Resort

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown
10.0 out of 10, Exceptional, (56)
"Everything about this rental is perfect. Beautiful, clean, well equipped, views, views views!!!!!! Hosts were amazing!!!!! We cannot wait to revisit this special place again!!!!!!!"
United States
Joseph S.
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
United States
Jessica
The price is NZ$283
includes taxes & fees
11 Nov - 12 Nov
Brewster Green Resort

Riverview Resort

3.0 star property
Bass River
9.2 out of 10, Wonderful, (168)
"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."
United States
Kathleen
Riverview Resort

InnSeason Resorts Captain's Quarters

3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Absolutely beautiful room amenities and view. Hands down the best place we have ever stayed at on the Cape. Definitely going back!!"
United States
Keith
InnSeason Resorts Captain's Quarters

Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Eastham
10.0 out of 10, Exceptional, (27)
"From the moment we arrived we were overtaken by the stunning views and private location. The accommodations and amenities went far beyond our high expectations. David is the ultimate host. He truly assisted us with all aspects of our stay. From changing our dates, to restaurant recommendations his guidance is genuine and compassionate. Thank you David, we appreciate all that you have done for us, and until the next time, may your visits to the Cape give you sunny days, and warm water!"
United States
Don H.
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Thomas Sea Suites

3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (94)
"Great location "
United States
John
Thomas Sea Suites

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Nantucket Town
10.0 out of 10, Exceptional, (287)
"Loved this cottage. It was perfect for the two of us plus our puppy. And it was in the perfect location: across the street from the Children's Beach, 4 houses down from the White Elephant and the Brant Point Grill restaurant, and 3 blocks from downtown Nantucket. It was new, spotless, charming and the appliances and accommodations were exemplary. Would definitely stay here again"
United States
Elizabeth M.
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (230)
"Perfect for a couple and two kids"
United States
Shelly R.
Steps to the Ocean! Perfect Location!!!

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Nantucket Town
10.0 out of 10, Exceptional, (176)
"Great place to stay! Walking distance to town and lovely yard to relax in."
United States
Danielle J.
The price is NZ$886
includes taxes & fees
1 Dec - 2 Dec
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
10.0 out of 10, Exceptional, (39)
"The house and property was simply amazing and such a perfect spot for our company team retreat of 12"
United States
Jennifer S.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Quaint condo near private beach access with fireplace - close to dining

Dennis Port
9.0 out of 10, Wonderful, (61)
"Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. "
United States
Rosemarie P.
The price is NZ$506
includes taxes & fees
17 Nov - 18 Nov
Quaint condo near private beach access with fireplace - close to dining

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

Nantucket
8.8 out of 10, Excellent, (81)
"Love this property! Has everything we needed. Great location. Close to bike path, beaches and Wave stop. Will definitely be back!"
United States
Michele L.
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

Cozy 4 bedroom cottage in town, with parking

2.0 star property
Nantucket Town
9.0 out of 10, Wonderful, (21)
"Loved the location, the outdoor shower, and the fact that we had beach towels and chairs. Tv and internet worked great. No book with house information anywhere. Needed kitchen towels and a few more bath towels. Shower curtain liner needs replaced. Loved nantuckett"
United States
Marcy H.
Cozy 4 bedroom cottage in town, with parking

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
8.2 out of 10, Very good, (71)
"Beautiful house great views of the river. Peaceful weekend away"
United States
Anthony G.
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

LUXURIOUS Cottage with Breathtaking Harbor Views

Nantucket Town
9.8 out of 10, Exceptional, (171)
"We loved this property and all talked about the next time we can book! The location is perfect and the interior is beautiful. Also super comfy beds!"
United States
Breanne N.
LUXURIOUS Cottage with Breathtaking Harbor Views

Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!

Nantucket Town
9.4 out of 10, Exceptional, (42)
"This home was fantastic for our large group for a long weekend. A 10 minute walk to downtown, the home was immaculate, very spacious (especially the large U-shape sectional in the living room, the kitchen was completely new, and the driveway was large enough for our two large vehicles. The owner was also great to deal with and provided answers to all of our questions. We hope to come back and stay again next year!!!"
United States
Stephen G.
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
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 favorite 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 depends 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 NZ$200 per night. Entering your travel dates in the search wizard you might find 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.