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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Eastern Massachusetts vacation homes

A covered outdoor deck with wicker furniture, a small table, and chairs.

1. 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 ￥39,218
￥60,102 total
includes taxes & fees
Oct 30 - Oct 31
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.

2. 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 ￥23,374
￥50,991 total
includes taxes & fees
Nov 15 - Nov 16
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'.

3. 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)
"Cute little place that is clean and well taken care of. Plum Island was adorable with a mile walk or ride to a great beach. Enjoyed our stay."
United States
Ann P.
The price is ￥20,550
￥60,795 total
includes taxes & fees
Nov 9 - Nov 10
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.

4. 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, (106 reviews)
"We had a great stay in a lovely house. Linda (the host) was very responsive. There are plenty of utensils and pots and pans to cook with. House was clean and met our expectations."
United States
Antony V.
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
A boat docked at a concrete pier with a sandy shore in the background.

5. 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 ￥24,707
￥67,954 total
includes taxes & fees
Oct 26 - Oct 27
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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, (59 reviews)
"Great overall stay!"
United States
Chris R.
The price is ￥30,354
￥70,878 total
includes taxes & fees
Nov 2 - Nov 3
Cozy three-bedroom home close to Boston w/ plenty of parking
New lighting throughout the first floor.

7. Right on the Cape Cod Canal and bike path!

Right on the Cape Cod Canal and bike path!
Bourne
10.0 out of 10, Exceptional, (32 reviews)
"The hosts were very accessible and helpful with questions and requests that we made. On several occasions they went above and beyond to make our stay perfect."
United States
Tracy G.
The price is ￥39,218
￥91,746 total
includes taxes & fees
Oct 26 - Oct 27
Right on the Cape Cod Canal and bike path!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

8. 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 ￥19,868
￥32,396 total
includes taxes & fees
Nov 4 - Nov 5
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

9. 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 ￥25,099
￥32,066 total
includes taxes & fees
Nov 2 - Nov 3
The Essex of Gloucester
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

10. Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
9.8 out of 10, Exceptional, (8 reviews)
"Perfect stay for the night. Communication was great and property was clean and had everything we needed."
United States
Ryan E.
The price is ￥25,884
￥45,033 total
includes taxes & fees
Nov 1 - Nov 2
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
A wooden deck with a table and chairs, an umbrella, and a view of the sea.

11. Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
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 ￥31,217
￥79,895 total
includes taxes & fees
Nov 15 - Nov 16
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
A wooden deck overlooking a calm lake with trees and houses in the background.

12. 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 ￥43,061
￥106,915 total
includes taxes & fees
Nov 1 - Nov 2
Stunning 4-bedroom Private Fresh Water Beach Front
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

13. 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, (108 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 ￥18,023
￥76,652 total
includes taxes & fees
Oct 27 - Oct 28
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A spacious room with a large bay window overlooking a beach, a fireplace, and a cozy seating area.

14. Love Sand, Madaket on the Beach, Lovely Seaside Home

Love Sand, Madaket on the Beach, Lovely Seaside Home
Nantucket
9.8 out of 10, Exceptional, (58 reviews)
"Almost 270 degree views of the ocean — spectacular setting with lots of privacy, great amenities and miles of beach to explore. Very accessible to town. We loved our stay!"
United States
Marjorie A.
The price is ￥129,575
￥259,534 total
includes taxes & fees
Nov 23 - Nov 24
Love Sand, Madaket on the Beach, Lovely Seaside Home
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 ￥24,908
￥82,368 total
includes taxes & fees
Oct 26 - Oct 27
The Alpine/Walk to Beach for 2 or more!
A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

16. Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Eastham
9.8 out of 10, Exceptional, (8 reviews)
"Clean well maintained"
United States
mark A.
The price is ￥24,392
￥81,060 total
includes taxes & fees
Nov 4 - Nov 5
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
A sandy beach with wooden posts and a clear view of the ocean.

17. Sand Bar~3 BR Dog Friendly Beachside Home

Sand Bar~3 BR Dog Friendly Beachside Home
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 ￥29,030
￥80,982 total
includes taxes & fees
Nov 4 - Nov 5
Sand Bar~3 BR Dog Friendly Beachside Home
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

18. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (63 reviews)
"Very nice little house with all amenities you can ask for. Unfortunately we only had a quick over night stay. Beautiful location. The drive way is a challenge to get out if you are backing out. We certainly would stay again!"
United States
Nicole
The price is ￥77,651
￥127,915 total
includes taxes & fees
Nov 1 - Nov 2
Beach Life Bliss - steps to the beach
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

19. 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 ￥28,237
￥81,512 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

20. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (18 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is ￥59,480
￥145,817 total
includes taxes & fees
Nov 1 - Nov 2
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Beautiful view"
Kevin 1-night trip
Posted 8 hours ago
citizenM Boston North Station

Find out more about Eastern Massachusetts

Eastern Massachusetts Vacation Homes information

Number of reviews
700
Accommodation
460 Vacation Homes
Lowest Price
￥32,066
Highest Price
￥259,534

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