Southeast Massachusetts Holiday Rentals

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Our top choices for Southeast Massachusetts holiday rentals

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (340)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
The price is NZ$254
includes taxes & fees
1 Jan - 2 Jan 2026
InnSeason Resorts Captain's Quarters
3.0 star property
8.0 out of 10, Very good, (1)
"This was a lovely spot to stay with my dog for a bit. Very clean and tidy. Would stay again"
United States
Kristin
The price is NZ$636
includes taxes & fees
9 Jan - 10 Jan 2026
7 Mi to Downtown Providence: Quiet Apt in Seekonk

Aparthotel in Brewster

Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (121)
"Loved your location. We were originally placed in one of the townhomes, but when the locks/key didn't work, we were upgraded to the stand-alone house #106, which was wonderful! We loved the entire house - kitchen was great and stocked perfectly and all the rooms were big and comfortable. We hope to be back again soon!"
United States
Kathleen
The price is NZ$370
includes taxes & fees
28 Dec - 29 Dec
Brewster Green Resort
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$884
includes taxes & fees
26 Dec - 27 Dec
Cozy Large Home in Harwich with Patio near Wequassett Resort
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is NZ$671
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.

Apartment in New Bedford

The Charming Gem Near The Water!
9.6 out of 10, Exceptional, (34)
"I had stayed here last year and it's so close to several of my family members. This is my go to place when I travel to the New Bedford area."
United States
Judy C.
The price is NZ$382
includes taxes & fees
25 Jan - 26 Jan 2026
The Charming Gem Near The Water!
9.6 out of 10, Exceptional, (5)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
United States
Laura D.
The price is NZ$528
includes taxes & fees
11 Jan - 12 Jan 2026
Make this charming, modern retreat your home away from home!!
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is NZ$736
includes taxes & fees
28 Dec - 29 Dec
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Aparthotel in West Yarmouth

The Cove at Yarmouth by Westgate Resorts
3.0 star property
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is NZ$253
includes taxes & fees
4 Jan - 5 Jan 2026
The Cove at Yarmouth by Westgate Resorts
10.0 out of 10, Exceptional, (129)
"Very clean and nice place for two for a quick peaceful stay. Great location."
United States
Michele G.
The price is NZ$656
includes taxes & fees
26 Dec - 27 Dec
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Holiday Home in New Bedford

Blue Haven Houseboat
2.0 star property
The price is NZ$237
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Haven Houseboat
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
The price is NZ$660
includes taxes & fees
1 Jan - 2 Jan 2026
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Aparthotel in Mashpee

Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
The price is NZ$278
includes taxes & fees
29 Dec - 30 Dec
Sea Mist Resort
10.0 out of 10, Exceptional, (18)
"Fun spot for the family or a group. Simple, but clean and themed well. "
United Kingdom
Kyle J.
The price is NZ$708
includes taxes & fees
26 Dec - 27 Dec
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is NZ$569
includes taxes & fees
4 Jan - 5 Jan 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.8 out of 10, Exceptional, (15)
"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "
United States
Candice C.
The price is NZ$688
includes taxes & fees
28 Dec - 29 Dec
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
2.0 star property
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
The price is NZ$1,226
includes taxes & fees
27 Dec - 28 Dec
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
7.6 out of 10, Good, (8)
"Easy to find, very comfortable, clean and convenient"
United States
David W.
The price is NZ$278
includes taxes & fees
4 Jan - 5 Jan 2026
Charming garden level 1 bedroom 1 bath apartment in Brockton
10.0 out of 10, Exceptional, (21)
"This is a wonderful place to stay with the amenities of home. Spacious, private, with lots of places nearby to see and explore."
United States
Becky P.
The price is NZ$365
includes taxes & fees
29 Dec - 30 Dec
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
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$254 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.