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 Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Eastern Massachusetts holiday 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
The price is NZ$762
includes taxes & fees
3 Nov - 4 Nov
Thomas Sea Suites
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,339 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
The price is NZ$248
includes taxes & fees
7 Nov - 8 Nov
Crescent Suites Hotel
A poolside area with sun loungers and umbrellas, a wooden deck, and a view of the ocean.

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
The price is NZ$353
includes taxes & fees
1 Nov - 2 Nov
The Club at New Seabury
A pool area with lounge chairs and flags.

4. 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, (270 reviews)
"The property is an older timeshare and dated."
United States
Kim
The price is NZ$217
includes taxes & fees
8 Nov - 9 Nov
The Cove at Yarmouth by Westgate Resorts
A balcony with two white chairs and two wine glasses, overlooking a beach with a clear sky.

5. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,296 reviews)
"Awesome location - cute property - kitchens well stocked."
United States
Candi
The price is NZ$200
includes taxes & fees
1 Nov - 2 Nov
Sandcastle Resort and Club
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, (678 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
The price is NZ$545
includes taxes & fees
22 Nov - 23 Nov
Marriott Vacation Club® at Custom House, Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. 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
The price is NZ$456
includes taxes & fees
1 Nov - 2 Nov
The Chester Hotel
A modern apartment with a dining area, kitchen, living room, and a large window.

8. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.0 out of 10, Wonderful, (95 reviews)
"This is our 3rd time and we will be back next year. Love the location, the place is perfect we truly enjoy our time. The response time for any questions is great."
United States
Kim
The price is NZ$594
includes taxes & fees
29 Nov - 30 Nov
Long Beach Suites
A large, multi-story hotel with a wooden exterior and multiple balconies. A wooden boardwalk leads to the entrance.

9. Harborview Nantucket

Harborview Nantucket
4.0 star property
Nantucket Town
9.4 out of 10, Exceptional, (22 reviews)
"Wonderful property. Very clean and modern. Close to everything downtown. Highly recommend!"
United States
John
The price is NZ$1,239
includes taxes & fees
5 Nov - 6 Nov
Harborview Nantucket
A living room with a leather sofa, a TV, a console table with decorative items, and a painting on the wall.

10. 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 NZ$800
includes taxes & fees
3 Nov - 4 Nov
Walk to Swift's Beach! Classic Cottage w/ Deck
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, (340 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is NZ$528
includes taxes & fees
10 Nov - 11 Nov
Kasa Boston at Fenway
A modern hotel room with a large bed, a sofa, a small table, and a view of the city.

12. Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (22 reviews)
"Several items were broken, damaged, or in disrepair upon arrival. An elevator alarm was ringing for at least 16 hours before being resolved late at night. Check in and check out process needs to be more clear and streamlined."
United States
Gina
The price is NZ$523
includes taxes & fees
30 Oct - 31 Oct
Furnished Apartments near Encore Boston
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
8.0 out of 10, Very good, (37 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is NZ$534
includes taxes & fees
2 Nov - 3 Nov
The Concord Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

14. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (769 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is NZ$421
includes taxes & fees
29 Nov - 30 Nov
Global Luxury Suites Downtown Boston
A row of brick buildings with storefronts, including a bakery and a liquor store.

15. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (213 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is NZ$434
includes taxes & fees
22 Nov - 23 Nov
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.

16. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (466 reviews)
"Great price for the place given the location."
United States
Beenish
The price is NZ$393
includes taxes & fees
10 Nov - 11 Nov
Maverick Suites at 28 Fenway
A two-story beach house with a balcony, a deck, and a sign reading "Plovers Nest".

17. Plovers Nest

Plovers Nest
3.0 star property
Newburyport
10.0 out of 10, Exceptional, (2 reviews)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
The price is NZ$693
includes taxes & fees
17 Nov - 18 Nov
Plovers Nest
A modern living room with a round dining table, grey sofas, and large windows offering city views.

18. Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
8.6 out of 10, Excellent, (17 reviews)
"spacious, clean, central location"
United States
Gregory
The price is NZ$552
includes taxes & fees
30 Oct - 31 Oct
Furnished Apts near Harvard Stadium
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

19. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
8.0 out of 10, Very good, (13 reviews)
"Great place, clean, well maintained and centrally located. Excellent and timely communication."
United States
Mike Shang-Yu
Furnished Apartment Near Longwood
A wooden interior with a dining area set for a meal, featuring a table with plates, glasses, and cutlery.

20. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
The price is NZ$693
includes taxes & fees
12 Nov - 13 Nov
Charming Family-friendly Getaway in Sandwich!
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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Amazing location. We’d go back there anytime. Loved having coffee shop there too wish they had sit down breakfast food cooked to order.but the convience worth it! It’s all about Location It was Perfect"
Lisa 2-night trip
Posted 3 hours ago
The Godfrey Hotel Boston

Find out more about Eastern Massachusetts

Everything you need to know about Eastern 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 Eastern 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 Eastern Massachusetts holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Eastern Massachusetts holiday 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 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 Eastern 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 Eastern 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 Eastern Massachusetts rentals

At Expedia, we put the best Eastern 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 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 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 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.