Southeast Massachusetts Vacation Homes

A lake surrounded by autumn-colored trees.

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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!!

Wareham

Edna R.

HK$2,298 total

includes taxes & fees

13 Oct - 14 Oct

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

Falmouth

HK$6,028 total

includes taxes & fees

12 Oct - 13 Oct

A beach with waves crashing onto the shore under a clear sky.

3. Oahusleeps 5near beachoutdoor showerfirepit*gas grill

Plymouth

Anonymous traveller

HK$2,709 total

includes taxes & fees

12 Oct - 13 Oct

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!

Seconsett Island

Kian S.

HK$3,575 total

includes taxes & fees

18 Oct - 19 Oct

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

"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!"

Bruce

HK$3,007 total

includes taxes & fees

9 Oct - 10 Oct

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.

Sandwich

Alysha D.

HK$4,024 total

includes taxes & fees

24 Oct - 25 Oct

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

Falmouth

Stephanie B.

HK$4,087 total

includes taxes & fees

1 Nov - 2 Nov

A wooden deck overlooking a calm lake with trees and houses in the background.

8. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

HK$5,456 total

includes taxes & fees

11 Oct - 12 Oct

A deck with a fire pit, outdoor seating, and a blue umbrella.

9. Cozy Cottage walk to Menauhant Beach

East Falmouth

Grace P.

HK$6,660 total

includes taxes & fees

12 Oct - 13 Oct

A sandy beach with a calm lake and a forested hill in the background.

10. Charming 3-bedroom house in lovely Barnstable

Barnstable

Cailee B.

HK$5,155 total

includes taxes & fees

12 Oct - 13 Oct

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

Barnstable

Jen M.

HK$3,971 total

includes taxes & fees

12 Oct - 13 Oct

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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

Oak Bluffs

Chris S.

HK$6,602 total

includes taxes & fees

14 Oct - 15 Oct

A kitchen with wooden cabinets, a dining table with chairs, and a kitchen island with baskets.

13. Cape Cod's "Beach Rose"

Dennis

Rachael M.

A beach with clear water and a sandy shore.

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

Little Neck Bay

Eric S.

HK$8,137 total

includes taxes & fees

30 Oct - 31 Oct

A circular stone patio with Adirondack chairs and a small table in a forested area.

15. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

HK$5,566 total

includes taxes & fees

12 Oct - 13 Oct

A modern bedroom with a wooden wall, a bed with grey bedding, a bedside table, a TV mounted on the wall, and a ceiling light.

16. Private Suite w/ Bath & Free Parking

Brockton

Robin

HK$1,496 total

includes taxes & fees

20 Oct - 21 Oct

A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

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

Oak Bluffs

Sherri R.

HK$10,729 total

includes taxes & fees

9 Oct - 10 Oct

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

18. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham

Mark K.

HK$4,011 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinetry, stainless steel appliances, a large island, and a view of greenery outside.

19. Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!

Yarmouth

Allison V.

HK$5,268 total

includes taxes & fees

18 Oct - 19 Oct

A beach with clear blue water and a sandy shore.

20. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable

Jim C.

HK$5,254 total

includes taxes & fees

12 Oct - 13 Oct

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Top Southeast Massachusetts Hotel Reviews

Iris Hotel Cape Cod

8/10 Good

"Room was clean, staff at the desk could be a bit more knowledgeable. I had a message on the phone and asked how to retrieve it. He didn't know. Breakfast was good except for the last 2 days. There was a different person in charge and the breakfast was terrible. 2 coffee pots were empty, Food trays were empty. I had to go to the kitchen and yell for someone to fill the coffee. Croissants were as hard as a rock. The person that was in charge the first few days we were there did an excellent job."

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