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

Holiday Rentals in Eastern Massachusetts

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Our top choices for Eastern Massachusetts holiday rentals

1. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,278 reviews)
"Loved the property, it was right on the beach and close to downtown."
United States
Christopher D
The price is €63
includes taxes & fees
25 Oct - 26 Oct
Sandcastle Resort and Club

2. 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 €132
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts

3. Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (128 reviews)
"Great location, clean and the room setup is perfect for family."
United States
Heather
The price is €380
includes taxes & fees
15 Oct - 16 Oct
Thomas Sea Suites

4. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
The price is €385
includes taxes & fees
13 Oct - 14 Oct
Charming Family-friendly Getaway in Sandwich!

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, (163 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 €350
includes taxes & fees
15 Oct - 16 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

6. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (28 reviews)
"The place was great, and the host was even better! Very good communication and great customer service. I would highly recommend!"
United States
Travis
The price is €223
includes taxes & fees
2 Nov - 3 Nov
Enjoyable 2-bedroom lower level apartment in charming Lynn

7. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (92 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is €295
includes taxes & fees
14 Oct - 15 Oct
New Seabury Cape Condo + Pool & Beach Escape

8. ♥ 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, (82 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 €331
includes taxes & fees
9 Nov - 10 Nov
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

9. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,308 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is €152
includes taxes & fees
31 Oct - 1 Nov
Crescent Suites Hotel

10. Coastal 1BR Retreat Spa Walk to Dining Water

Coastal 1BR Retreat Spa Walk to Dining Water
2.0 star property
Warren
The price is €332
includes taxes & fees
14 Oct - 15 Oct
Coastal 1BR Retreat Spa Walk to Dining Water

11. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (95 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is €299
includes taxes & fees
18 Oct - 19 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖

12. Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (33 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 €408
includes taxes & fees
1 Nov - 2 Nov
Amazing Onset Getaway in the Starfish Suite

13. 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)
"Excellent above garage large studio in a superb Rockport location central to everything. Hosts were gracious and warm and made the overnight stay a good one. Highly recommend."
United States
Eugene
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

14. Best location in Ptown,1 Bedroom,PARKING/WaterVIEW

Best location in Ptown,1 Bedroom,PARKING/WaterVIEW
Provincetown
8.8 out of 10, Excellent, (35 reviews)
"It was a great stay and felt like home. Will book again in the future!"
United States
Jeremy D.
The price is €162
includes taxes & fees
9 Nov - 10 Nov
Best location in Ptown,1 Bedroom,PARKING/WaterVIEW

15. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (68 reviews)
"Clean, great location. "
United States
Peter G.
The price is €413
includes taxes & fees
19 Oct - 20 Oct
On Town Cove with salt water access! Kayaks and paddle board available for use!

16. 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 €236
includes taxes & fees
1 Nov - 2 Nov
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

17. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (107 reviews)
"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."
United States
Mark K.
The price is €478
includes taxes & fees
9 Nov - 10 Nov
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

18. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
The price is €355
includes taxes & fees
12 Oct - 13 Oct
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

19. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is €477
includes taxes & fees
24 Oct - 25 Oct
Brand new! Lovely apartment-Vineyard Haven

20. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.8 out of 10, Exceptional, (16 reviews)
"It was a great stay!"
United States
Adina S.
The price is €290
includes taxes & fees
29 Oct - 30 Oct
Light-filled Studio | Back Bay
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

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, 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 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 €63 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.