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

Search Vacation Homes in Eastern Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Eastern Massachusetts vacation homes

Beach

1. Mayflower*sleeps 5*near beach*firepit*outdoor shwr*grill

Mayflower*sleeps 5*near beach*firepit*outdoor shwr*grill
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"What a great place to stay! Comfortable little bungalow with just a short walk to the beach. Everything we needed was right there. Our little dog loved it too, would stay here again."
United States
Andrew E.
The price is ￥28,083
￥62,959 total
includes taxes & fees
Sep 2 - Sep 3
Mayflower*sleeps 5*near beach*firepit*outdoor shwr*grill
Beach

2. Sintra*romantic*near beach*private outdoor shower

Sintra*romantic*near beach*private outdoor shower
Plymouth
10.0 out of 10, Exceptional, (15 reviews)
"Such a great little space. The owners put so much into it to make it a wonderful vacation home. They thought of all the vacationers needs. We had a wonderful time in Plymouth."
United States
Robert C.
The price is ￥27,594
￥62,409 total
includes taxes & fees
Sep 17 - Sep 18
Sintra*romantic*near beach*private outdoor shower
Beach

3. 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 ￥24,405
￥58,171 total
includes taxes & fees
Sep 2 - Sep 3
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
Private kitchen

4. 3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful place and close to everything!"
United States
Erin A.
The price is ￥63,644
￥125,520 total
includes taxes & fees
Sep 7 - Sep 8
3BR3Bth Entire House/Steps to Downtown & TD Garden
Terrace/patio

5. 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, (156 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 ￥39,800
￥60,994 total
includes taxes & fees
Sep 2 - Sep 3
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Terrace/patio

6. Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.6 out of 10, Exceptional, (37 reviews)
"Loved the private outdoor patio"
United States
Robin P.
The price is ￥33,287
￥62,430 total
includes taxes & fees
Sep 20 - Sep 21
Gorgeous Beacon Hills Studio next to State house
Beach

7. 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 ￥28,513
￥57,812 total
includes taxes & fees
Sep 2 - Sep 3
Make this charming, modern retreat your home away from home!!
Room

8. The Cape Cod Loft | Near Beaches & Canal

The Cape Cod Loft | Near Beaches & Canal
Bourne
10.0 out of 10, Exceptional, (25 reviews)
"Really good place to stay close to Cape Cod and enjoy to visit the place ! Beautiful neighborhood and beautiful loft! Will come back for sure"
Canada
Olivier S.
The price is ￥23,985
￥50,228 total
includes taxes & fees
Sep 2 - Sep 3
The Cape Cod Loft | Near Beaches & Canal
Exterior detail

9. 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 ￥30,447
￥65,307 total
includes taxes & fees
Sep 1 - Sep 2
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
Living area

10. Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.2 out of 10, Wonderful, (26 reviews)
"Place is as advertised in the post/photos. The host is very friendly and attentive. Had small issue with keypad entry but worked through it with host."
United States
Nathan S.
The price is ￥20,059
￥62,678 total
includes taxes & fees
Sep 7 - Sep 8
Oldest Town of Cape Cod In The Historic District
Private kitchen

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

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
9.6 out of 10, Exceptional, (4 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 ￥26,268
￥45,702 total
includes taxes & fees
Sep 23 - Sep 24
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Living area

12. Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay

Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay
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 ￥80,591
￥151,574 total
includes taxes & fees
Sep 22 - Sep 23
Home with spectacular panoramic ocean views from a bluff high above Cape Cod Bay
Beach

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, (18 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 ￥28,513
￥66,882 total
includes taxes & fees
Sep 2 - Sep 3
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Interior

14. Easy access! 1br, 5 min walk to T train, easy access to Highway

Easy access! 1br, 5 min walk to T train, easy access to Highway
Westwood
9.2 out of 10, Wonderful, (17 reviews)
"Great location. Clean and private."
United States
Eric B.
The price is ￥20,928
￥44,903 total
includes taxes & fees
Aug 30 - Aug 31
Easy access! 1br, 5 min walk to T train, easy access to Highway
Private kitchen

15. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay. "
United States
Mary D.
The price is ￥25,238
￥65,908 total
includes taxes & fees
Sep 7 - Sep 8
2BR Historic Marblehead Home+Minutes to Beach
Room

16. 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, (53 reviews)
"Great overall stay!"
United States
Chris R.
The price is ￥35,119
￥77,478 total
includes taxes & fees
Sep 7 - Sep 8
Cozy three-bedroom home close to Boston w/ plenty of parking
Interior

17. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Quincy
9.6 out of 10, Exceptional, (54 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is ￥28,836
￥62,987 total
includes taxes & fees
Aug 30 - Aug 31
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Living area

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

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (26 reviews)
"Loved this property. "
United States
Carol S.
The price is ￥16,716
￥77,131 total
includes taxes & fees
Aug 30 - Aug 31
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Private kitchen

19. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (11 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 ￥28,974
￥36,987 total
includes taxes & fees
Sep 14 - Sep 15
The Essex of Gloucester
Living area

20. 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, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is ￥24,368
￥94,683 total
includes taxes & fees
Aug 31 - Sep 1
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Massachusetts Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Loved the Lemon water in the lobby, the decor of our room. It was difficult having the microwave way down in the lobby. I will be prepared for that next stay."
Susan 3-night trip
Posted 2 hours ago
Harborside Inn Of Boston

Find out more about Eastern Massachusetts

Eastern Massachusetts Vacation Homes information

Number of reviews
726
Accommodation
355 Vacation Homes
Lowest Price
￥36,987
Highest Price
￥151,574

Explore a world of travel with Expedia