A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Eastern Massachusetts Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Eastern Massachusetts vacation rentals

A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.

1. Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (131 reviews)
"Great location, clean and the room setup is perfect for family."
United States
Heather
$457 nightly
The price is $511
Nov 8 - Nov 9
Total with taxes and fees
Thomas Sea Suites
A balcony with two white chairs and two wine glasses, overlooking a beach with a clear sky.

2. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,303 reviews)
"Awesome location - cute property - kitchens well stocked."
United States
Candi
$98 nightly
The price is $112
Nov 19 - Nov 20
Total with taxes and fees
Sandcastle Resort and Club
A golf course with a clubhouse, a lake, and surrounding trees.

3. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$147 nightly
The price is $169
Nov 19 - Nov 20
Total with taxes and fees
The Club at New Seabury
A covered outdoor deck with wicker furniture, a small table, and chairs.

4. 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, (168 reviews)
"We thoroughly enjoyed our stay! The property was very clean, decorately beautifully, and had everything we needed. The bottle of wine and snacks made for a nice welcome. The location and gorgeous view were beyond measure and the deck and yard are set up perfectly for watching the sunrise and relaxing by the bay. The owners are on site but that was not an issue because the space is very private. Highly recommend!"
United States
Bruce
$272 nightly
The price is $304
Dec 1 - Dec 2
Total with taxes and fees
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

5. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,345 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
$140 nightly
The price is $157
Nov 8 - Nov 9
Total with taxes and fees
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (680 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
$229 nightly
The price is $263
Nov 25 - Nov 26
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
A pool area with lounge chairs and flags.

7. 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, (272 reviews)
"The property is an older timeshare and dated."
United States
Kim
$107 nightly
The price is $122
Nov 9 - Nov 10
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

8. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 reviews)
"Charming historic building with modern room interiors and amenities, high quality linens/towels, and an easy walk to BSO, Northeastern University, and shopping."
United States
Andrew
$270 nightly
The price is $310
Nov 22 - Nov 23
Total with taxes and fees
The Chester Hotel
A spacious living room with a grey sofa set, a coffee table, and a ceiling fan. Large windows provide a view of the cityscape.

9. Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
Duxbury
10.0 out of 10, Exceptional, (37 reviews)
"Excellent place, we will be returning. "
United States
Kevan
$432 nightly
The price is $457
Nov 6 - Nov 7
Total with taxes and fees
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
A modern apartment with a dining area, kitchen, living room, and a large window.

10. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (97 reviews)
"In a very convenient location. Not far from the train station. Walking dust to the beach. Room was very clean and comfortable."
United States
Jessie
Long Beach Suites
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

11. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (347 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
$270 nightly
The price is $297
Nov 10 - Nov 11
Total with taxes and fees
Kasa Boston at Fenway
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

12. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
$206 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
Global Luxury Suites Downtown Boston
A wooden interior with a dining area set for a meal, featuring a table with plates, glasses, and cutlery.

13. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
$341 nightly
The price is $390
Nov 8 - Nov 9
Total with taxes and fees
Charming Family-friendly Getaway in Sandwich!
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

14. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
$199 nightly
The price is $229
Dec 1 - Dec 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

15. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (38 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
$259 nightly
The price is $298
Nov 11 - Nov 12
Total with taxes and fees
The Concord Hotel
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

16. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"We had a great visit and the house gave us everything we needed for a comfortable stay. The rooms were nicely furnished and the bedrooms were spacious. The location was convenient for accessing the bus and the subway. The host was very friendly and responsive. We hope to visit again!"
United States
Christina B.
$477 nightly
The price is $548
Nov 23 - Nov 24
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A living room with a beige sofa, a glass coffee table, and a TV on a wooden cabinet.

17. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (49 reviews)
"Lovely flat in a convenient part of town with lots of supermarket and facilities nearby. We loved our stay."
United States
Thomas C.
$190 nightly
The price is $212
Nov 8 - Nov 9
Total with taxes and fees
The Charming Gem Near The Water!
A modern hotel room with a bed, a desk, a sofa, and a dining area.

18. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (246 reviews)
"Spacers, convenient location"
United States
Svetlana
$322 nightly
The price is $370
Nov 23 - Nov 24
Total with taxes and fees
Charlesgate Suites
A circular wooden sauna with a door, surrounded by wooden walls and potted plants.

19. Top Floor Loft 3BR w Skylights Spa Walkable

Top Floor Loft 3BR w Skylights Spa Walkable
2.0 star property
Warren
$462 nightly
The price is $526
Nov 9 - Nov 10
Total with taxes and fees
Top Floor Loft 3BR w Skylights Spa Walkable
A wooden hallway with a patterned floor leading to a door.

20. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (355 reviews)
"The area was walkable and the room was great!"
United States
Edna
$194 nightly
The price is $217
Dec 1 - Dec 2
Total with taxes and fees
Maverick Suites at 89 Marion
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 Eastern Massachusetts Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"beautiful landscaping, impeccably clean rooms, spotless bathrooms. They upgraded att no charge for our wedding anniversary, (they forgot my quirky note to my husband that I wanted waiting with the champagne and strawberries otherwise perfect) easy check in easy check out. left up by $400 myself and he up by $700. ty Encore Boston!! see y'all next year."
Sarah-Lynn 1-night trip
Posted less than an hour ago
Encore Boston Harbor

Find out more about Eastern Massachusetts

Everything you need to know about Eastern Massachusetts vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Massachusetts vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Eastern Massachusetts vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Massachusetts vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Massachusetts. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Eastern Massachusetts in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Eastern Massachusetts rentals

At Expedia, we put the best Eastern Massachusetts vacation 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 Eastern 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 Eastern Massachusetts vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Eastern 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.

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