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

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 AU$584
includes taxes & fees
22 Oct - 23 Oct
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, (1,326 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is AU$213
includes taxes & fees
4 Nov - 5 Nov
Crescent Suites Hotel
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

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 AU$283
includes taxes & fees
15 Nov - 16 Nov
The Club at New Seabury
A balcony with two white chairs and two wine glasses, overlooking a beach with a clear sky.

4. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,291 reviews)
"A bit on the older side, but still a good location, and comfy room space."
United States
Eugene
The price is AU$101
includes taxes & fees
25 Oct - 26 Oct
Sandcastle Resort and Club
A covered outdoor deck with wicker furniture, a small table, and chairs.

5. 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, (167 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
The price is AU$534
includes taxes & fees
30 Oct - 31 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

6. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is AU$424
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

7. 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, (677 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is AU$585
includes taxes & fees
11 Nov - 12 Nov
Marriott Vacation Club® at Custom House, Boston
A pool area with lounge chairs and flags.

8. 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, (269 reviews)
"The property is an older timeshare and dated."
United States
Kim
The price is AU$175
includes taxes & fees
1 Nov - 2 Nov
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.

9. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (41 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is AU$369
includes taxes & fees
1 Nov - 2 Nov
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.

10. 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
The price is AU$584
includes taxes & fees
22 Oct - 23 Oct
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
A modern apartment with a dining area, kitchen, living room, and a large window.

11. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (92 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 AU$504
includes taxes & fees
16 Nov - 17 Nov
Long Beach Suites
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, (766 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is AU$465
includes taxes & fees
25 Oct - 26 Oct
Global Luxury Suites Downtown Boston
A single-story house with a front door, a small porch, and a fenced yard.

13. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
The price is AU$579
includes taxes & fees
23 Oct - 24 Oct
Charming Family-friendly Getaway in Sandwich!
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

14. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (35 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is AU$474
includes taxes & fees
3 Nov - 4 Nov
The Concord Hotel
A dining area with a wooden table, white chairs, and a television on a cabinet.

15. 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 AU$369
includes taxes & fees
2 Nov - 3 Nov
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
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)
"Is a great place"
United States
Ramon G.
The price is AU$780
includes taxes & fees
4 Nov - 5 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A modern hotel room with a bed, a desk, a sofa, and a dining area.

17. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (243 reviews)
"Spacers, convenient location"
United States
Svetlana
The price is AU$538
includes taxes & fees
9 Nov - 10 Nov
Charlesgate Suites
A harbor with numerous boats and a prominent building with a clock tower in the background.

18. ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (84 reviews)
"I honestly had my favorite stay of all time at this place. It was clean cozy and absolutely everything that we needed. I love the historical feel to it and it was perfection."
United States
Arianna
The price is AU$424
includes taxes & fees
27 Oct - 28 Oct
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
A coastal town with houses along the beach and a view of the sea.

19. Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (35 reviews)
"Comfortable apartment that was within walking distance to multiple restaurants, a very nice park, and the beach. We had a great time."
United States
Kim W.
The price is AU$630
includes taxes & fees
2 Nov - 3 Nov
Amazing Onset Getaway in the Starfish Suite
A beach with houses in the background and people engaging in various activities.

20. Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (222 reviews)
"Wonderful place to stay! Highly recommend!"
United States
Sara D.
The price is AU$356
includes taxes & fees
22 Oct - 23 Oct
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
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 Eastern Massachusetts Hotel Reviews

The Revolution Hotel

The Revolution Hotel

8/10 Good
"Really nice little room at a cute hotel. Staff was very helpful and kind. We had a queen with a private bathroom and it was very small but exactly what I was expecting. Unfortunately the room above us had some issue with their door that caused it to hit the floor above us loudly every time it opened, which made it hard to fall asleep. We did also hear somebody get mugged outside of our window on the street. But everybody was very friendly and helpful."
Will 3-night trip
Posted 1 hour ago
The Revolution Hotel

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 favourite 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 depend 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 AU$101 per night. Entering your travel dates in the search wizard might find you 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.