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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Eastern Massachusetts vacation 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
9.8 out of 10, Exceptional, (20 reviews)
"Johanna and Costas were the most gracious hosts. The bungalow was exactly what we needed! Excellent stay!"
United States
Anonymous traveler
The price is AED 506
AED 1,268 total
includes taxes & fees
1 Nov - 2 Nov
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
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 AED 493
AED 1,075 total
includes taxes & fees
13 Oct - 14 Oct
Make this charming, modern retreat your home away from home!!
A covered outdoor deck with wicker furniture, a small table, and chairs.

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, (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 AED 918
AED 1,407 total
includes taxes & fees
16 Oct - 17 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

4. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (59 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is AED 485
AED 1,325 total
includes taxes & fees
20 Oct - 21 Oct
Beach Life Bliss - steps to the beach
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, (104 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 AED 915
AED 1,883 total
includes taxes & fees
24 Oct - 25 Oct
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.

6. 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, (44 reviews)
"Great stay!"
United States
Kian S.
The price is AED 643
AED 1,673 total
includes taxes & fees
8 Oct - 9 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

7. 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 Essex of Gloucester
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

8. 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
9.8 out of 10, Exceptional, (106 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 AED 349
AED 1,877 total
includes taxes & fees
13 Oct - 14 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A kitchen with wooden cabinets, a dining table with chairs, and a kitchen island with baskets.

9. Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful home very easy check in and out host was great will definitely be staying their again in the future"
United States
Rachael M.
Cape Cod's "Beach Rose"
A covered outdoor deck with a view of the ocean, string lights, a table with a vase of flowers, and a patterned rug.

10. Soak in the Hot Tub! Water Views and Ocean Scent!

Soak in the Hot Tub! Water Views and Ocean Scent!
Scituate
10.0 out of 10, Exceptional, (12 reviews)
"Even though the weather wasnt very cooperative, it was a great stay, cozy warm and felt like being at home, the host was very pleasant and easy to communicate with, And the veiw is amazing"
United States
Stephen T.
Soak in the Hot Tub! Water Views and Ocean Scent!
A wooden front door with a glass panel and the number 383.

11. 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)
"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 AED 704
AED 1,488 total
includes taxes & fees
12 Oct - 13 Oct
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
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 AED 1,098
AED 2,494 total
includes taxes & fees
19 Oct - 20 Oct
Village Colonial / Harbor Views.
A two-story house with a front porch and a garden with purple flowers.

13. ✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (36 reviews)
"Wonderful stay"
United States
Brent H.
The price is AED 404
AED 699 total
includes taxes & fees
12 Oct - 13 Oct
✨Private Studio w/ Loft Center Historic Carlisle✨
A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

14. 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 AED 678
AED 1,594 total
includes taxes & fees
18 Oct - 19 Oct
Cozy three-bedroom home close to Boston w/ plenty of parking
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

15. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
9.0 out of 10, Wonderful, (11 reviews)
"Nice location, quiet neighborhood, comfortable, and clean with a feeling of newness. Nice time of year to enjoy the porch and there was plenty of room for our group of seven. Three couches in the basement! Easy to get to town or beaches, etc. Host was helpful and communicative."
United States
Jen M.
The price is AED 446
AED 1,775 total
includes taxes & fees
8 Oct - 9 Oct
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

16. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.2 out of 10, Wonderful, (27 reviews)
"Property is convenient to beaches and restaurants."
United States
Laurie and Rick A.
The price is AED 268
AED 1,618 total
includes taxes & fees
8 Oct - 9 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A wooden deck overlooking a calm lake with trees and houses in the background.

17. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (44 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 AED 1,041
AED 2,554 total
includes taxes & fees
11 Oct - 12 Oct
Stunning 4-bedroom Private Fresh Water Beach Front
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

18. 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 AED 661
AED 1,913 total
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A living room with a grey sofa, striped rug, and a lamp.

19. 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, (29 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 AED 599
AED 1,901 total
includes taxes & fees
28 Oct - 29 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
A sandy beach with wooden posts and a clear view of the ocean.

20. Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (33 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 AED 704
AED 1,941 total
includes taxes & fees
19 Oct - 20 Oct
Sand Bar-Dog Friendly on Cooks Brook 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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

8/10 Good
"Hotel was perfect location. Clean, rooms good - staff excellent"
Jane 1-night trip
Posted less than an hour ago
Hilton Boston Park Plaza