Holiday Homes in Eastern Massachusetts

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Our top choices for Eastern Massachusetts holiday homes

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, (168 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 AU$435
includes taxes & fees
1 Dec - 2 Dec
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

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 AU$462
includes taxes & fees
10 Nov - 11 Nov
Make this charming, modern retreat your home away from home!!

3. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.8 out of 10, Exceptional, (8 reviews)
"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...
United States
Maura
The price is AU$512
includes taxes & fees
10 Nov - 11 Nov
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

4. Plovers Nest

Plovers Nest
3.0 star property
Newburyport
10.0 out of 10, Exceptional, (2 reviews)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
The price is AU$557
includes taxes & fees
17 Nov - 18 Nov
Plovers Nest

5. Panoramic Cape Cod Bay Views with Private Sandy Beach

Panoramic Cape Cod Bay Views with Private Sandy Beach
Plymouth
10.0 out of 10, Exceptional, (10 reviews)
"The view alone is worth every penny and will definitely visit again. The property is small but is perfect for two to four people. It’s a beautiful, quaint, quiet seaside neighborhood just a few miles from downtown Plymouth. The cottage itself was well laid out for the small space and the views from the moment you walk in are breathtaking. Can’t wait to book my next stay there."
United States
Dawn c.
The price is AU$733
includes taxes & fees
11 Nov - 12 Nov
Panoramic Cape Cod Bay Views with Private Sandy Beach

6. 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 AU$218
includes taxes & fees
17 Nov - 18 Nov
Private Suite w/ Bath & Free Parking

7. Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton
Brockton
8.6 out of 10, Excellent, (19 reviews)
"Pet friendly"
United States
John
The price is AU$240
includes taxes & fees
11 Nov - 12 Nov
Charming garden level 1 bedroom 1 bath apartment in Brockton

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)
"Nice place but quite expensive."
United States
Jeremy P.
The price is AU$1,250
includes taxes & fees
30 Nov - 1 Dec
Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat

9. 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 AU$624
includes taxes & fees
10 Nov - 11 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

10. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful and relaxing location."
United States
Lauren F.
The price is AU$687
includes taxes & fees
30 Nov - 1 Dec
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

11. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • 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 AU$468
includes taxes & fees
10 Nov - 11 Nov
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

12. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.6 out of 10, Exceptional, (11 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is AU$302
includes taxes & fees
11 Nov - 12 Nov
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

13. 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, (60 reviews)
"Great overall stay!"
United States
Chris R.
The price is AU$616
includes taxes & fees
10 Nov - 11 Nov
Cozy three-bedroom home close to Boston w/ plenty of parking

14. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.8 out of 10, Exceptional, (16 reviews)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
The price is AU$588
includes taxes & fees
10 Nov - 11 Nov
Oceanside Village Home~Private Fenced Yard~Reserved Parking

15. 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, (23 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 AU$554
includes taxes & fees
15 Nov - 16 Nov
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

16. Convenient Central Location• Slps 8• Walk 2 Beach

Convenient Central Location• Slps 8• Walk 2 Beach
Scituate
10.0 out of 10, Exceptional, (14 reviews)
"A great location near everything."
United States
Robert
The price is AU$945
includes taxes & fees
10 Nov - 11 Nov
Convenient Central Location• Slps 8• Walk 2 Beach

17. Spectacular Bayfront Cottage with Private Deck & Sunset Views

Spectacular Bayfront Cottage with Private Deck & Sunset Views
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 AU$682
includes taxes & fees
6 Dec - 7 Dec
Spectacular Bayfront Cottage with Private Deck & Sunset Views

18. 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, (109 reviews)
"Clean, well-appointed, quaint, pet-friendly home centrally located in a great area for driving to Harding's Beach and downtown Chatham."
United States
Jennifer B.
The price is AU$752
includes taxes & fees
7 Dec - 8 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

19. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (18 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 AU$297
includes taxes & fees
16 Nov - 17 Nov
The Essex of Gloucester

20. LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Nantucket Town
10.0 out of 10, Exceptional, (202 reviews)
"Great stay again"
United States
Ray S.
The price is AU$773
includes taxes & fees
14 Nov - 15 Nov
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
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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