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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Our top choices for Eastern Massachusetts vacation homes

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)
"Property was in great location and central to all the areas of Plymouth worth visiting. Property had heating and air and the communal fire pit area was great and lighted. There was a great park across the street from the bungalows which provided great morning walks and sunrises. If ya have a pet it would make for a great stay."
United States
Jeffrey
The price is ¥21,775
¥54,553 total
includes taxes & fees
Oct 21 - Oct 22
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill

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 ¥21,190
¥48,205 total
includes taxes & fees
Oct 22 - Oct 23
Make this charming, modern retreat your home away from home!!

3. 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, (165 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 ¥39,505
¥60,542 total
includes taxes & fees
Oct 18 - Oct 19
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

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.
The price is ¥20,701
¥61,241 total
includes taxes & fees
Nov 9 - Nov 10
Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

5. 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 ¥18,915
¥28,188 total
includes taxes & fees
Oct 27 - Oct 28
Private Suite w/ Bath & Free Parking

6. 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 ¥35,412
¥75,797 total
includes taxes & fees
Oct 24 - Oct 25
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.

7. 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 ¥24,888
¥68,453 total
includes taxes & fees
Oct 18 - Oct 19
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

8. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (62 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is ¥78,220
¥130,087 total
includes taxes & fees
Nov 1 - Nov 2
Beach Life Bliss - steps to the beach

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, (58 reviews)
"Great overall stay!"
United States
Chris R.
The price is ¥29,155
¥69,104 total
includes taxes & fees
Oct 18 - Oct 19
Cozy three-bedroom home close to Boston w/ plenty of parking

10. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (14 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 ¥35,889
¥45,916 total
includes taxes & fees
Nov 3 - Nov 4
The Essex of Gloucester

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 ¥17,537
¥75,966 total
includes taxes & fees
Oct 18 - Oct 19
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

12. 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)
"We had a fantastic stay at this cottage. The location was absolutely perfect- right on the beach with beautiful views and easy access to the water. Our dog especially loved running on the beach during low tide, which was one of the highlights of our trip. The cottage was comfortable, clean, and well-equipped. We would happily stay here again!"
United States
edyta d.
The price is ¥31,446
¥80,481 total
includes taxes & fees
Nov 15 - Nov 16
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

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 ¥28,444
¥82,289 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

14. 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 ¥28,723
¥81,525 total
includes taxes & fees
Oct 26 - Oct 27
Sand Bar~3 BR Dog Friendly Beachside Home

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 ¥25,090
¥82,971 total
includes taxes & fees
Oct 26 - Oct 27
The Alpine/Walk to Beach for 2 or more!

16. Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
10.0 out of 10, Exceptional, (61 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 ¥47,248
¥107,996 total
includes taxes & fees
Oct 19 - Oct 20
Village Colonial / Harbor Views.

17. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Extraordinarily beautiful VRBO, very clean, convenient to highway, walking distance to several eateries, walk or quick drive to the Red Line to use to get into downtown Boston, and very responsive owner."
United States
Mark T.
The price is ¥35,618
¥69,439 total
includes taxes & fees
Nov 1 - Nov 2
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

18. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (99 reviews)
"Such a great experience! Loved the property"
United States
Alex B.
The price is ¥51,673
¥106,259 total
includes taxes & fees
Oct 18 - Oct 19
Nantucket - edge of town

19. 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 ¥22,123
¥78,584 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Large Home in Harwich with Patio near Wequassett Resort

20. Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (37 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is ¥25,655
¥116,170 total
includes taxes & fees
Oct 19 - Oct 20
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
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

Eastern Massachusetts Vacation Homes information

Number of reviews
1,270
Accommodation
460 Vacation Homes
Lowest Price
¥28,188
Highest Price
¥130,087