A lake surrounded by autumn-colored trees.

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

Our top choices for Southeast Massachusetts holiday homes

A sandy beach with a forest in the background and a clear sky.

1. 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 NZ$565
includes taxes & fees
13 Oct - 14 Oct
Make this charming, modern retreat your home away from home!!
A bedroom with a bed, two windows with curtains, a door, a bedside table with a lamp, and a picture on the wall.

2. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is NZ$1,360
includes taxes & fees
5 Oct - 6 Oct
West Falmouth Family Retreat Near Chapoquoit Beach
A beach with waves crashing onto the shore under a clear sky.

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 traveller
The price is NZ$599
includes taxes & fees
6 Oct - 7 Oct
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
A covered outdoor deck with wicker furniture, a small table, and chairs.

4. 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 NZ$680
includes taxes & fees
5 Oct - 6 Oct
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
A boat docked at a concrete pier with a sandy shore in the background.

5. 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 NZ$805
includes taxes & fees
6 Oct - 7 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A house with a front porch, a white door, and a number '36' on the wall.

6. 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 NZ$913
includes taxes & fees
24 Oct - 25 Oct
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
A wooden deck overlooking a calm lake with trees and houses in the background.

7. 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 NZ$1,228
includes taxes & fees
11 Oct - 12 Oct
Stunning 4-bedroom Private Fresh Water Beach Front
A water park with a large central pool, multiple slides, and a variety of play structures.

8. 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)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is NZ$991
includes taxes & fees
31 Oct - 1 Nov
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A deck with a fire pit, outdoor seating, and a blue umbrella.

9. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is NZ$1,435
includes taxes & fees
8 Oct - 9 Oct
Cozy Cottage walk to Menauhant Beach
A sandy beach with a calm lake and a forested hill in the background.

10. Charming 3-bedroom house in lovely Barnstable

Charming 3-bedroom house in lovely Barnstable
Barnstable
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay! Loved the home! "
United States
Cailee B.
The price is NZ$1,168
includes taxes & fees
12 Oct - 13 Oct
Charming 3-bedroom house in lovely Barnstable
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

11. 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 NZ$893
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A beach with clear water, people sunbathing, and a house in the background.

12. 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, (7 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
The price is NZ$1,359
includes taxes & fees
5 Oct - 6 Oct
4BR + No Bridge Traffic + Water Wizz Water Park + Pond & Beaches
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

13. 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 NZ$870
includes taxes & fees
5 Oct - 6 Oct
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A wooden deck with a table and chairs, surrounded by a wooden fence and large windows.

14. Classic Cape Escape in Charming Cotuit

Classic Cape Escape in Charming Cotuit
Contuit
9.0 out of 10, Wonderful, (6 reviews)
"Loved the location and walking path across the way. Very comfortable and spacious home. Would definitely revisit again. "
United States
Michelle
The price is NZ$1,900
includes taxes & fees
7 Oct - 8 Oct
Classic Cape Escape in Charming Cotuit
A backyard with a seating area, a white fence, and a variety of plants.

15. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is NZ$2,037
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

16. 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 NZ$1,456
includes taxes & fees
8 Oct - 9 Oct
Oak Bluffs 4BR • 5 Min Drive to Downtown
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

17. 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 NZ$773
includes taxes & fees
6 Oct - 7 Oct
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A beach with clear water and a sandy shore.

18. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (53 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is NZ$1,804
includes taxes & fees
30 Oct - 31 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A modern kitchen with white cabinetry, a central island, skylights, and a view of the outdoors.

19. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"The home worked out well for our needs. They have a very nice fully fenced in yard which was very beneficial."
United States
Rosemary P.
The price is NZ$2,098
includes taxes & fees
6 Oct - 7 Oct
Recently renovated 3 bedroom
A cozy living room with a view of the ocean, featuring a sofa, a coffee table, and a dining area.

20. 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.
Whale Away Panoramic Cape Cod Bay Views from a 5-Bedroom Bluff-Top Retreat
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 Southeast Massachusetts Hotel Reviews

Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

10/10 Excellent
"Great place to stay at a great price. Rooms were clean and the free breakfast was good!"
Kent 2-night trip
Posted 1 hour ago
Sunbird Cape Cod Resort

Find out more about Southeast Massachusetts

Southeast Massachusetts Holiday Homes information

Number of reviews
843
Accommodation
751 Holiday Homes
Lowest Price
NZ$565
Highest Price
NZ$2,098