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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Our top choices for Eastern Massachusetts holiday homes

1. Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Santorini*themed*priv. yard*near beach* firepit*outdoor shwr
Plymouth
10.0 out of 10, Exceptional, (20 reviews)
"Very nice place. I’d stay there again!"
United States
Jamie C.
The price is NZ$477
includes taxes & fees
29 Oct - 30 Oct
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

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, (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 NZ$645
includes taxes & fees
30 Oct - 31 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

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 NZ$547
includes taxes & fees
15 Nov - 16 Nov
Make this charming, modern retreat your home away from home!!

4. SeaGlass Walk to Beach, Firepit, Ext Shower, Pets

SeaGlass Walk to Beach, Firepit, Ext Shower, Pets
Plymouth
10.0 out of 10, Exceptional, (23 reviews)
"Very nice property and location and hosts"
United States
PETER K.
SeaGlass Walk to Beach, Firepit, Ext Shower, Pets

5. 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$691
includes taxes & fees
17 Nov - 18 Nov
Plovers Nest

6. Panoramic Cape Cod Bay Views with Private Sandy Beach

Panoramic Cape Cod Bay Views with Private Sandy Beach
Plymouth
10.0 out of 10, Exceptional, (9 reviews)
"The view alone is worth every penny and will definitely visit again. The property is small but is perfect for two to four people. It’s a beautiful, quaint, quiet seaside neighborhood just a few miles from downtown Plymouth. The cottage itself was well laid out for the small space and the views from the moment you walk in are breathtaking. Can’t wait to book my next stay there."
United States
Dawn c.
The price is NZ$962
includes taxes & fees
10 Nov - 11 Nov
Panoramic Cape Cod Bay Views with Private Sandy Beach

7. Private Suite w/ Bath & Free Parking

Private Suite w/ Bath & Free Parking
Brockton
10.0 out of 10, Exceptional, (5 reviews)
"It was a very nice little place with a convienient patio deck."
United States
Robin
The price is NZ$291
includes taxes & fees
3 Nov - 4 Nov
Private Suite w/ Bath & Free Parking

8. Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton
Brockton
8.6 out of 10, Excellent, (19 reviews)
"Pet friendly"
United States
John
The price is NZ$303
includes taxes & fees
2 Nov - 3 Nov
Charming garden level 1 bedroom 1 bath apartment in Brockton

9. 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, (59 reviews)
"Great overall stay!"
United States
Chris R.
The price is NZ$767
includes taxes & fees
2 Nov - 3 Nov
Cozy three-bedroom home close to Boston w/ plenty of parking

10. 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 place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is NZ$754
includes taxes & fees
1 Nov - 2 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

11. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is NZ$1,002
includes taxes & fees
31 Oct - 1 Nov
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

12. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.4 out of 10, Exceptional, (10 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is NZ$357
includes taxes & fees
4 Nov - 5 Nov
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

13. Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Bayside
9.8 out of 10, Exceptional, (21 reviews)
"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "
United States
Candice C.
The price is NZ$694
includes taxes & fees
2 Nov - 3 Nov
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

14. Scituate Seaside Escape – Sleeps 8, Walk to Beach

Scituate Seaside Escape – Sleeps 8, Walk to Beach
Scituate
10.0 out of 10, Exceptional, (14 reviews)
"A great location near everything."
United States
Robert
The price is NZ$1,081
includes taxes & fees
28 Oct - 29 Oct
Scituate Seaside Escape – Sleeps 8, Walk to Beach

15. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (16 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is NZ$354
includes taxes & fees
4 Nov - 5 Nov
The Essex of Gloucester

16. 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 NZ$1,152
includes taxes & fees
1 Nov - 2 Nov
Stunning 4-bedroom Private Fresh Water Beach Front

17. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (100 reviews)
"Such a great experience! Loved the property"
United States
Alex B.
The price is NZ$1,148
includes taxes & fees
8 Nov - 9 Nov
Nantucket - edge of town

18. Spectacular Bayfront Cottage with Private Deck & Sunset Views

Spectacular Bayfront Cottage with Private Deck & Sunset Views
Wellfleet
10.0 out of 10, Exceptional, (85 reviews)
"Amazing stay at this pet-friendly cottage on the beach. Location was great and the hosts were very accommodating. We loved the privacy of the island, the outdoor space, and the sunsets overlooking the bay!"
United States
Scott M.
The price is NZ$894
includes taxes & fees
15 Nov - 16 Nov
Spectacular Bayfront Cottage with Private Deck & Sunset Views

19. 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)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is NZ$815
includes taxes & fees
11 Nov - 12 Nov
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

20. 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, (225 reviews)
"Great location "
United States
Stephanie B.
The price is NZ$902
includes taxes & fees
2 Nov - 3 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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

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Eastern Massachusetts Holiday Homes information

Number of reviews
570
Accommodation
476 Holiday Homes
Lowest Price
NZ$291
Highest Price
NZ$1,152