Holiday Homes in Southeast Massachusetts

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Our top choices for Southeast Massachusetts holiday homes

1. Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
8.8 out of 10, Excellent, (5 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is €314
includes taxes & fees
9 Nov - 10 Nov
Cozy Riverfront Stay in Wareham

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 €291
includes taxes & fees
10 Nov - 11 Nov
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, (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 €271
includes taxes & fees
1 Dec - 2 Dec
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

4. 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 €401
includes taxes & fees
9 Nov - 10 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

5. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is €918
includes taxes & fees
9 Nov - 10 Nov
West Falmouth Family Retreat Near Chapoquoit Beach

6. Breathtaking Riverfront Hideaway in Wareham

Breathtaking Riverfront Hideaway in Wareham
Wareham
9.4 out of 10, Exceptional, (3 reviews)
"Private setting with lovely viewVery clean and spacious housePerfect for out of town wedding guests"
United States
Karleen L.
The price is €514
includes taxes & fees
9 Nov - 10 Nov
Breathtaking Riverfront Hideaway in Wareham

7. 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 €423
includes taxes & fees
30 Nov - 1 Dec
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

8. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Dartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is €266
includes taxes & fees
11 Nov - 12 Nov
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

9. 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, (227 reviews)
"Great location "
United States
Stephanie B.
The price is €473
includes taxes & fees
9 Nov - 10 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10. 4BR + No Bridge Traffic + Water Wizz Water Park + Pond & Beaches

4BR + No Bridge Traffic + Water Wizz Water Park + Pond & Beaches
Bourne
10.0 out of 10, Exceptional, (8 reviews)
"We survived the blizzard with no power outage. The house had everything we needed.. We ate, drank, played games and put a puzzle together. Thank you for a great stay. Location is awesome!"
United States
Anonymous traveller
4BR + No Bridge Traffic + Water Wizz Water Park + Pond & Beaches

11. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is €740
includes taxes & fees
1 Dec - 2 Dec
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

12. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is €876
includes taxes & fees
19 Nov - 20 Nov
Coastal chic meets French Provençal in this newly renovated oceanfront home.

13. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is €630
includes taxes & fees
20 Nov - 21 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

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 €441
includes taxes & fees
9 Nov - 10 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

15. 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 €826
includes taxes & fees
30 Nov - 1 Dec
Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat

16. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is €573
includes taxes & fees
9 Nov - 10 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

17. Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!
West Barnstable
10.0 out of 10, Exceptional, (150 reviews)
"Great fit for our family!"
United States
William H.
The price is €1,512
includes taxes & fees
23 Nov - 24 Nov
Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

18. Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Barnstable
8.4 out of 10, Very good, (10 reviews)
"Easy check in, lots of room for people. Needs a little updating and it will be perfect."
United States
Austin S.
The price is €973
includes taxes & fees
14 Nov - 15 Nov
Spacious Lake House for Large Groups w Private Acre+ short path to Lake

19. 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 €438
includes taxes & fees
7 Dec - 8 Dec
Panoramic Cape Cod Bay Views with Private Sandy Beach

20. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is €364
includes taxes & fees
9 Nov - 10 Nov
Sal's Place
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.

Learn more about Southeast Massachusetts

Unmissable purely for its history, this region also offers spectacular coastal scenery and a rich cultural community.

A calm river with reflections of houses and trees.