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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 ￥21,694
￥54,350 total
includes taxes & fees
Oct 4 - Oct 5
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, (162 reviews)
"Beautiful view extremely clean easy check in/out. LOTS of amenities. Everything you could need or want is there!!"
United States
Roseanne
The price is ￥39,358
￥60,317 total
includes taxes & fees
Oct 4 - Oct 5
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 ￥23,457
￥51,173 total
includes taxes & fees
Oct 13 - Oct 14
Make this charming, modern retreat your home away from home!!
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, (57 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is ￥20,544
￥56,486 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥39,200
￥79,460 total
includes taxes & fees
Oct 24 - Oct 25
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 ￥27,550
￥72,252 total
includes taxes & fees
Oct 6 - Oct 7
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

7. 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 ￥15,013
￥79,687 total
includes taxes & fees
Oct 27 - Oct 28
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A cozy living room with a view of the ocean, featuring a sofa, a coffee table, and a dining area.

8. Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat

Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat
Plymouth
10.0 out of 10, Exceptional, (77 reviews)
"It was an amazing place to stay. The outside heater element looking over the Ocean was amazing! "
United States
Chance4 C.
The price is ￥73,819
￥142,421 total
includes taxes & fees
Oct 5 - Oct 6
Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat
A beach with a clear sky and a child walking on the sand.

9. 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, (20 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 ￥29,868
￥68,489 total
includes taxes & fees
Nov 2 - Nov 3
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
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)
"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 ￥25,443
￥32,480 total
includes taxes & fees
Oct 7 - Oct 8
The Essex of Gloucester
A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

11. 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 ￥37,547
￥79,044 total
includes taxes & fees
Oct 6 - Oct 7
Cozy three-bedroom home close to Boston w/ plenty of parking
A two-story house with a front porch and a garden with purple flowers.

12. ✨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 ￥14,065
￥26,559 total
includes taxes & fees
Oct 5 - Oct 6
✨Private Studio w/ Loft Center Historic Carlisle✨
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

13. 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 ￥10,746
￥68,403 total
includes taxes & fees
Oct 5 - Oct 6
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

14. 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 ￥22,124
￥79,966 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A wooden deck overlooking a calm lake with trees and houses in the background.

15. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (43 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 ￥44,631
￥109,278 total
includes taxes & fees
Oct 13 - Oct 14
Stunning 4-bedroom Private Fresh Water Beach Front
A beach with a wooden fence and a clear view of the ocean.

16. 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 ￥24,997
￥82,662 total
includes taxes & fees
Oct 4 - Oct 5
The Alpine/Walk to Beach for 2 or more!
A living room with a sofa, coffee table, and a view of the kitchen.

17. Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
9.8 out of 10, Exceptional, (60 reviews)
"Second time staying at this beautiful Cohasset destination and home. Would love to come back again. Excellent location, harbor walks, downtown walks, comfortable beds, well appointed kitchen, everything you need!"
United States
Beth G.
The price is ￥47,072
￥106,729 total
includes taxes & fees
Oct 5 - Oct 6
Village Colonial / Harbor Views.
A spacious living room with a large sliding glass door leading to an outdoor patio, a ceiling fan, and a white sofa with patterned cushions.

18. 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 ￥36,398
￥128,683 total
includes taxes & fees
Oct 3 - Oct 4
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A wooden staircase with a railing leading to a covered deck area.

19. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
9.8 out of 10, Exceptional, (20 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is ￥41,099
￥99,718 total
includes taxes & fees
Oct 7 - Oct 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A wooden front door with a glass panel and the number 383.

20. 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, (52 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 ￥26,779
￥59,631 total
includes taxes & fees
Oct 4 - Oct 5
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"It is a very nice hotel. Public transportation is right outside the door which covers most of the Boston area. Location is ideal for downtown activities. Most of the touristy stuff is within walking distance."
Jeremy 2-night trip
Posted 5 hours ago
Harborside Inn Of Boston

Find out more about Eastern Massachusetts

Eastern Massachusetts Vacation Homes information

Number of reviews
972
Accommodation
460 Vacation Homes
Lowest Price
￥26,559
Highest Price
￥142,421

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