A lake surrounded by autumn-colored trees.

Southeast Massachusetts Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southeast Massachusetts holiday rentals

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

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 HK$1,585
HK$1,814 total
includes taxes & fees
7 Sept - 8 Sept
The Club at New Seabury
A living room with a leather sofa, a TV, a console table with decorative items, and a painting on the wall.

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 HK$1,552
HK$4,037 total
includes taxes & fees
31 Aug - 1 Sept
Walk to Swift's Beach! Classic Cottage w/ Deck
A pool area with lounge chairs and flags.

3. 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 HK$1,367
HK$1,565 total
includes taxes & fees
24 Sept - 25 Sept
The Cove at Yarmouth by Westgate Resorts
A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.

4. 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 HK$2,669
HK$3,334 total
includes taxes & fees
1 Sept - 2 Sept
Thomas Sea Suites
A hot tub with a tiled edge and a metal ladder, surrounded by a carpeted floor and wooden walls.

5. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (141 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
The price is HK$1,717
HK$1,965 total
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort
A balcony with two white chairs and two wine glasses, overlooking a beach with a clear sky.

6. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,246 reviews)
"Location small drive to all the activities and down town Fun experience"
United States
debra
The price is HK$769
HK$880 total
includes taxes & fees
27 Sept - 28 Sept
Sandcastle Resort and Club
Beach chairs arranged in rows facing the ocean.

7. Edgewater Beach Resort

Edgewater Beach Resort
3.5 star property
Dennis Port
9.0 out of 10, Wonderful, (339 reviews)
"Great place! Everything was lovely"
United States
Susan
The price is HK$2,739
HK$3,134 total
includes taxes & fees
31 Aug - 1 Sept
Edgewater Beach Resort
A beach with sand, flowers, and a clear sky.

8. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is HK$4,328
HK$5,894 total
includes taxes & fees
31 Aug - 1 Sept
Sal's Place
A modern building with a curved glass facade, surrounded by well-manicured gardens and a sign indicating it is a hotel.

9. Holly Tree Resort

Holly Tree Resort
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (412 reviews)
"Check in was easy, rooms clean, easy location."
United States
William S
The price is HK$1,852
HK$2,120 total
includes taxes & fees
31 Aug - 1 Sept
Holly Tree Resort
A covered deck with a grill, outdoor furniture, and a view of trees.

10. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is HK$1,129
HK$5,408 total
includes taxes & fees
1 Sept - 2 Sept
6 Mi to Beach: Home w/ Deck in Brewster!
A beachfront property with a wooden deck, outdoor seating, and a view of the ocean.

11. Walk to Commercial Street! Couples Retreat w/ Deck

Walk to Commercial Street! Couples Retreat w/ Deck
3.0 star property
Provincetown
The price is HK$1,615
HK$4,812 total
includes taxes & fees
2 Sept - 3 Sept
Walk to Commercial Street! Couples Retreat w/ Deck

12. Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is HK$5,974
HK$10,262 total
includes taxes & fees
31 Aug - 1 Sept
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

13. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.8 out of 10, Good, (19 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is HK$1,468
HK$2,678 total
includes taxes & fees
1 Sept - 2 Sept
The Concord Hotel
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is HK$1,390
HK$2,589 total
includes taxes & fees
2 Sept - 3 Sept
The Chester Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

15. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (661 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is HK$2,193
HK$2,520 total
includes taxes & fees
6 Sept - 7 Sept
Marriott Vacation Club® at Custom House, Boston
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

16. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (143 reviews)
"Worth the stay"
Canada
Akansha
The price is HK$1,101
HK$1,986 total
includes taxes & fees
31 Aug - 1 Sept
Maverick Suites at 40 Temple St
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

17. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (452 reviews)
"Great location so close to everything"
United States
Hunter
The price is HK$762
HK$1,372 total
includes taxes & fees
31 Aug - 1 Sept
Temple Place Suites
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

18. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (309 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is HK$1,616
HK$2,669 total
includes taxes & fees
7 Sept - 8 Sept
Kasa Boston at Fenway
A row of brick buildings with storefronts, including a bakery and a liquor store.

19. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (201 reviews)
"Great location, really cool place!"
United States
lane
The price is HK$1,171
HK$2,067 total
includes taxes & fees
31 Aug - 1 Sept
Maverick Suites at 245 Newbury St
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

20. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (411 reviews)
"Good clear communication. Great location! Walked to Fenway for a game. All kinds of restaurants close. Nice clean, comfortable room in a beautifully maintained building!"
United States
James
The price is HK$1,701
HK$2,722 total
includes taxes & fees
1 Sept - 2 Sept
Maverick Suites at 28 Fenway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southeast Massachusetts Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Pros-The pool inside and outside were great and the gaming room had a good selection. The free breakfast had a good variety and fire pit on site bar where we could toast samores. It was very picturesque and not too far from the bars and restaurants on Main Street. Cons- the room was damp and housing keeping pretty non existent. We got new towels but the room was not cleaned most days ."
Mr. Anthony 4-night trip
Posted 5 hours ago
Bayside Resort Hotel

Find out more about Southeast Massachusetts

Search for holiday rentals in Southeast Massachusetts on Expedia! You can easily find your home rentals, villas, holiday apartments in Southeast Massachusetts using one of the methods below:

  • View our selection of featured holiday rentals in Southeast Massachusetts
  • Use the map to find apartments and other holiday homes in the Southeast Massachusetts neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southeast Massachusetts while they last

Look no further and take a look at our great range of rental properties in Southeast Massachusetts!