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

Holiday Homes in Eastern Massachusetts

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Eastern Massachusetts holiday homes

A beach with waves crashing onto the shore under a clear sky.

1. Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill

Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
Plymouth
10.0 out of 10, Exceptional, (21 reviews)
The price is €302
includes taxes & fees
25 Oct - 26 Oct
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
A covered outdoor deck with wicker furniture, a small table, and chairs.

2. 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, (164 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 €351
includes taxes & fees
15 Oct - 16 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
A sandy beach with a forest in the background and a clear sky.

3. Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
10.0 out of 10, Exceptional, (12 reviews)
"Very clean, comfortable and updated house. We had a great stay!"
United States
Edna R.
The price is €288
includes taxes & fees
22 Oct - 23 Oct
Make this charming, modern retreat your home away from home!!
A spacious kitchen with a dining area, a balcony with a view, and a sign reading 'BEACH HOUSE'.

4. Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
Newburyport
9.8 out of 10, Exceptional, (91 reviews)
"Perfect for two! Loved our stay and the hosts were kind and very easy to communicate with if you had any questions. Already planning my next stay"
United States
Laura M.
Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
A house with a front porch, a white door, and a number '36' on the wall.

5. Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.

Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
Sandwich
9.8 out of 10, Exceptional, (105 reviews)
"This property was the perfect beach house for our weekend trip. Everything looked exactly like the photos, was clean and accurate. The owner made check-in and check-out extremely clear on expectations and definitely provided a reasonable price for its amazing location. I will be staying here again!"
United States
Alysha D.
The price is €441
includes taxes & fees
24 Oct - 25 Oct
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

6. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (58 reviews)
"Great overall stay!"
United States
Chris R.
The price is €393
includes taxes & fees
18 Oct - 19 Oct
Cozy three-bedroom home close to Boston w/ plenty of parking
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

7. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (61 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is €327
includes taxes & fees
20 Oct - 21 Oct
Beach Life Bliss - steps to the beach
A boat docked at a concrete pier with a sandy shore in the background.

8. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great stay!"
United States
Kian S.
The price is €420
includes taxes & fees
18 Oct - 19 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A wooden front door with a glass panel and the number 383.

9. 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 €393
includes taxes & fees
1 Nov - 2 Nov
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

10. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 reviews)
The price is €257
includes taxes & fees
4 Nov - 5 Nov
The Essex of Gloucester
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

11. 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 €451
includes taxes & fees
19 Oct - 20 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A living room with a sofa, coffee table, and a view of the kitchen.

12. Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
9.8 out of 10, Exceptional, (60 reviews)
"This was the perfect stay for our family as we celebrated a wedding at the Red Lion Inn!!! It made everything so easy!"
United States
Kelly C.
The price is €619
includes taxes & fees
14 Oct - 15 Oct
Village Colonial / Harbor Views.
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

13. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (224 reviews)
"Great location "
United States
Stephanie B.
The price is €470
includes taxes & fees
2 Nov - 3 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

14. Historic Marblehead Nautical Home • Minutes to Salem

Historic Marblehead Nautical Home • Minutes to Salem
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay at this property. It is in a great location. Easy to walk to restaurants and stores in Marblehead. It was nice to not have to spend more time in our car after driving from Georgia. Property had everything we needed to live comfortably during our stay."
United States
Kevin H.
The price is €539
includes taxes & fees
18 Oct - 19 Oct
Historic Marblehead Nautical Home • Minutes to Salem
A beach with a wooden fence and a clear view of the ocean.

15. The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!
Eastham
9.2 out of 10, Wonderful, (12 reviews)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is €473
includes taxes & fees
14 Oct - 15 Oct
The Alpine/Walk to Beach for 2 or more!
A living room with a grey sofa, striped rug, and a lamp.

16. The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (30 reviews)
"We had such a wonderful time at the Surf Shack. The location was perfect. Within 15 minutes the best beaches, best dining, best shopping..everything. The house was incredibly clean with all the amenities needed to have a great family vacation. The host was incredibly quick to reply to any and all inquiries and was so pleasant to deal with. We couldn’t be any happier with our stay and will definitely stay there again if our travels return us to the Cape."
United States
Justin R.
The price is €465
includes taxes & fees
26 Oct - 27 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
A resort with a large pool, sun loungers, and a pier extending into the water.

17. Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is €433
includes taxes & fees
27 Oct - 28 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort
A sandy beach with wooden posts and a clear view of the ocean.

18. Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (34 reviews)
"We had a lovely visit with access to the beach and very comfortable beds. Enjoyed a beautiful sunset!"
United States
Debra H.
The price is €473
includes taxes & fees
14 Oct - 15 Oct
Sand Bar-Dog Friendly on Cooks Brook Beach
A wooden deck overlooking a calm lake with trees and houses in the background.

19. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is €631
includes taxes & fees
25 Oct - 26 Oct
Stunning 4-bedroom Private Fresh Water Beach Front
A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

20. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (45 reviews)
"Our family of four humans and two tiny dogs enjoyed our stay at this cozy home. The neighborhood is cute, quiet, and perfectly located to get in and out of town easily. The high appliances made cooking, laundry, and dishes convenient. We‘d love to stay here again."
United States
Bridget H.
The price is €558
includes taxes & fees
2 Nov - 3 Nov
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
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
"The Godfrey is in a perfect location, easily walkable to most downtown sites and the freedom trail. The staff were friendly and helpful and the hotel was clean and well maintained. The room was a little small but perfect for what we needed."
Jennifer 4-night trip
Posted less than an hour ago
The Godfrey Hotel Boston

Find out more about Eastern Massachusetts

Eastern Massachusetts Holiday Homes information

Number of reviews
1,161
Accommodation
486 Holiday Homes
Lowest Price
€257
Highest Price
€631