A lake surrounded by autumn-colored trees.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southeast Massachusetts vacation 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 ￥23,520
￥51,309 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥33,464
￥122,147 total
includes taxes & fees
Oct 6 - Oct 7
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 traveler
The price is ￥21,752
￥54,495 total
includes taxes & fees
Oct 6 - Oct 7
Oahu*sleeps 5*near beach*outdoor shower*firepit*gas grill
A boat docked at a concrete pier with a sandy shore in the background.

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, (44 reviews)
"Great stay!"
United States
Kian S.
The price is ￥27,624
￥72,446 total
includes taxes & fees
Oct 6 - Oct 7
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A covered outdoor deck with wicker furniture, a small table, and chairs.

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, (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 ￥39,463
￥60,478 total
includes taxes & fees
Oct 8 - Oct 9
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
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 ￥39,305
￥80,395 total
includes taxes & fees
Oct 24 - Oct 25
Town Neck Beach , Sandwich, MA, Cape Cod. Treehouse Brewery, marina, cc canal.
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

7. 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 ￥28,413
￥82,562 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A wooden deck overlooking a calm lake with trees and houses in the background.

8. 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 ￥44,750
￥109,208 total
includes taxes & fees
Oct 11 - Oct 12
Stunning 4-bedroom Private Fresh Water Beach Front
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 ￥37,109
￥128,460 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥39,778
￥103,698 total
includes taxes & fees
Oct 12 - Oct 13
Charming 3-bedroom house in lovely Barnstable
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

11. 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 ￥19,889
￥77,080 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A backyard with a seating area, a white fence, and a variety of plants.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is ￥70,748
￥180,585 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs
A wooden deck with a table and chairs, surrounded by a wooden fence and large windows.

13. 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 ￥51,046
￥168,426 total
includes taxes & fees
Oct 7 - Oct 8
Classic Cape Escape in Charming Cotuit
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

14. 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 ￥56,684
￥132,787 total
includes taxes & fees
Oct 8 - Oct 9
Oak Bluffs 4BR • 5 Min Drive to Downtown
A kitchen with wooden cabinets, a dining table with chairs, and a kitchen island with baskets.

15. Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful home very easy check in and out host was great will definitely be staying their again in the future"
United States
Rachael M.
The price is ￥27,703
￥35,861 total
includes taxes & fees
Oct 9 - Oct 10
Cape Cod's "Beach Rose"
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

16. 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 ￥10,734
￥68,326 total
includes taxes & fees
Oct 6 - Oct 7
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A room with a bay window, wooden beams, and three potted plants on the sill.

17. Welcome home. Comfortable four bedroom , two bath house

Welcome home. Comfortable four bedroom , two bath house
Plymouth
9.6 out of 10, Exceptional, (26 reviews)
"Awesome place to stay, Hope to stay there again soon"
United States
Kris
The price is ￥52,706
￥97,485 total
includes taxes & fees
Oct 13 - Oct 14
Welcome home. Comfortable four bedroom , two bath house
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 ￥70,401
￥164,401 total
includes taxes & fees
Oct 30 - Oct 31
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

19. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ￥62,824
￥215,814 total
includes taxes & fees
Oct 6 - Oct 7
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A circular stone patio with Adirondack chairs and a small table in a forested area.

20. 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 ￥49,881
￥112,844 total
includes taxes & fees
Oct 6 - Oct 7
1 Mi to Ferry Terminal: Oak Bluffs Family 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.
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Top Southeast Massachusetts Hotel Reviews

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"Loved staying here. Definitely will be back!"
Kevin 1-night trip
Posted 3 hours ago
Red Jacket Beach Resort

Find out more about Southeast Massachusetts

Southeast Massachusetts Vacation Homes information

Number of reviews
796
Accommodation
751 Vacation Homes
Lowest Price
￥35,861
Highest Price
￥215,814

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