A lake surrounded by autumn-colored trees.

Holiday Rentals in Southeast Massachusetts

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Our top choices for Southeast Massachusetts holiday rentals

1. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is €212
includes taxes & fees
8 Sept - 9 Sept
The Club at New Seabury

2. Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"3 of us had a great time in Wareham. The cottage was exactly as advertised and close to many beaches"
United States
Tracy
The price is €443
includes taxes & fees
9 Sept - 10 Sept
Walk to Swift's Beach! Classic Cottage w/ Deck

3. Beach & Waterpark Cottage near Cape Cod! Pet-Free Smoke-Free for Allergy Safety

Beach & Waterpark Cottage near Cape Cod! Pet-Free Smoke-Free for Allergy Safety
Wareham
9.8 out of 10, Exceptional, (16 reviews)
"Enjoyed the stay, would definitely come back!"
United States
Daniel W.
The price is €369
includes taxes & fees
8 Sept - 9 Sept
Beach & Waterpark Cottage near Cape Cod! Pet-Free Smoke-Free for Allergy Safety

4. Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
Bourne
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. "
United States
Ronald
The price is €258
includes taxes & fees
8 Sept - 9 Sept
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

5. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (89 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is €297
includes taxes & fees
13 Sept - 14 Sept
New Seabury Cape Condo + Pool & Beach Escape

6. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (46 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
The price is €198
includes taxes & fees
21 Sept - 22 Sept
The Charming Gem Near The Water!

7. Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (30 reviews)
"This location is really wonderful. What a cute town and the house had everything we needed. "
United States
Tony and Beck V.
The price is €425
includes taxes & fees
1 Oct - 2 Oct
Amazing Onset Getaway in the Starfish Suite

8. Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
10.0 out of 10, Exceptional, (12 reviews)
"Very clean, comfortable and updated house. We had a great stay!"
United States
Edna R.
The price is €309
includes taxes & fees
8 Sept - 9 Sept
Make this charming, modern retreat your home away from home!!

9. Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (160 reviews)
"Beautiful view extremely clean easy check in/out. LOTS of amenities. Everything you could need or want is there!!"
United States
Roseanne
The price is €337
includes taxes & fees
14 Sept - 15 Sept
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

10. The Cape Cod Loft | Near Beaches & Canal

The Cape Cod Loft | Near Beaches & Canal
Bourne
10.0 out of 10, Exceptional, (25 reviews)
"Really good place to stay close to Cape Cod and enjoy to visit the place ! Beautiful neighborhood and beautiful loft! Will come back for sure"
Canada
Olivier S.
The price is €284
includes taxes & fees
8 Sept - 9 Sept
The Cape Cod Loft | Near Beaches & Canal

11. Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (124 reviews)
"Great location, clean and the room setup is perfect for family."
United States
Heather
The price is €369
includes taxes & fees
8 Sept - 9 Sept
Thomas Sea Suites

12. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is €369
includes taxes & fees
8 Sept - 9 Sept
Brand new! Lovely apartment-Vineyard Haven

13. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
The price is €172
includes taxes & fees
23 Sept - 24 Sept
The Cove at Yarmouth by Westgate Resorts

14. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (142 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
The price is €216
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort

15. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (95 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is €465
includes taxes & fees
10 Sept - 11 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

16. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (42 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is €629
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

17. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (16 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is €443
includes taxes & fees
10 Sept - 11 Sept
Charming cottage overlooking the bay in Padanaram Village.

18. Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Dennis
10.0 out of 10, Exceptional, (138 reviews)
"Everything was perfect just like every other time we stayed! Louise makes you feel like you are home away from home...everything one needs is available. Thank you again for the memories!!"
United States
Kimberly C.
The price is €233
includes taxes & fees
14 Sept - 15 Sept
Pond View~ Abuts conservation and walking trails. There is fishing at the pond

19. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (221 reviews)
The price is €555
includes taxes & fees
7 Oct - 8 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive 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 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, apart-hotels, 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 €51 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.