A lake surrounded by autumn-colored trees.

Winery Hotels & Resorts in Southeast Massachusetts from NZ$248

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Check availability on Southeast Massachusetts Winery Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Southeast Massachusetts hotels with winery

A two-story house with a stone facade, a balcony, and a well-maintained garden.
A room with a large window, a dining table with a tablecloth, and a chair with a cushion.
A garden patio with stone steps, a table and chairs, and a large umbrella.
A park with a wooden staircase, lush greenery, and blooming pink flowers.

1. Frederick William House

Frederick William House
Falmouth
United States
David
NZ$493
includes taxes & fees
22 Oct - 23 Oct
Frederick William House
A cozy lounge area with leather sofas, striped armchairs, a fireplace, and a bookshelf.
A bathroom with a marble sink, a white toilet, and a shower area.
A library with bookshelves, a vase, and a table with chairs.
A room with a dark brown wall, a black leather sofa, a wooden dining table with chairs, a lamp, and framed pictures.

2. The Drew Hotel

The Drew Hotel
Plymouth Downtown Waterfront District
United States
Robert
NZ$352
includes taxes & fees
6 Oct - 7 Oct
The Drew Hotel
A two-story house with a front porch, a stone wall, and a well-maintained garden.
A staircase with a railing decorated with lights, a table with a lamp, and a chair.
A stone pathway leading through a lush garden with dense foliage and a variety of plants.
A pathway leading to a house with a stone wall, a white bench, and a gate.

3. Delano Homestead Bed & Breakfast

Delano Homestead Bed & Breakfast
Fairhaven
United States
Michael
NZ$434
includes taxes & fees
1 Oct - 2 Oct
Delano Homestead Bed & Breakfast
A waterfront property with a large house, a sandy beach, and a person fishing.
A room with a brick wall, a round table with two chairs, a fire extinguisher, and a sign that reads "BISDENGEN GUEST HOUSE".
A bedroom with a large bed, a desk, a chair, and a window with curtains.
A cozy living room with a red brick wall, a vintage refrigerator, a small table with chairs, and a patterned rug.

4. Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!

Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
Wareham
United States
Jaimie
NZ$633
includes taxes & fees
1 Oct - 2 Oct
Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
A poolside area with a wooden pergola, green seating, and a sign reading "LE JARDIN BLEU".
A modern indoor dining area with a wooden table, chairs, and a decorative wall with string lights.
A bartender pouring a drink into a gold cocktail shaker.
A row of white bicycles with brown seats and wicker baskets, parked in front of a white building with black railings and large windows.

5. Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection
West Yarmouth
United States
Omar
NZ$248
includes taxes & fees
14 Oct - 15 Oct
Uncommoner Hotel by Reverie Boutique Collection
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.
A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.
A spacious lobby with a reception desk, a large sofa, and a chandelier.
A two-story building with a symmetrical facade, large glass doors, and a brick-paved entrance.

6. Faraway Martha's Vineyard

Faraway Martha's Vineyard
Edgartown
United States
Thomas
NZ$568
includes taxes & fees
27 Oct - 28 Oct
Faraway Martha's Vineyard
A two-story residential building with a well-maintained lawn, a wooden fence, and a patio area with outdoor furniture.
A beach with clear water, a sandy shore, and houses in the background.
A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.
A staircase with wooden steps and a white wall. There is a white sofa with a geometric pillow in the living area.

7. Kingfisher Harwich Port

Kingfisher Harwich Port
Harwich Port
United States
Marc
NZ$464
includes taxes & fees
1 Oct - 2 Oct
Kingfisher Harwich Port
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
A living room with wicker furniture, a fireplace, and a staircase.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.

8. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
Canada
Ashley
NZ$439
includes taxes & fees
29 Oct - 30 Oct
Chatham Wayside Inn
A water park with a large central pool, multiple slides, and a variety of play structures.
A living room with a fireplace, a recliner, and a television on a mantel.
A patio with outdoor furniture, a tree, and a lattice fence.
A room with a wooden interior, a chair, a table, and large windows offering a view of a grassy field and a bridge.

9. 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
United States
Jainessa
NZ$987
includes taxes & fees
31 Oct - 1 Nov
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.
A waterfront hotel with outdoor seating and a view of the marina.
A storefront with a sign reading "SEA BAGS" and a chalkboard sign advertising handmade totes and accessories.
A modern kitchen with a central island, built-in appliances, and wicker chairs.

10. Thomas Sea Suites

Thomas Sea Suites
Plymouth Downtown Waterfront District
United States
Heather
NZ$757
includes taxes & fees
1 Oct - 2 Oct
Thomas Sea Suites
View all properties

Top Southeast Massachusetts Hotel Reviews

Inn on the Square

Inn on the Square

8/10 Good
"Property is a bit tired, but comfortable. Certainly a welcome stay when the ferries aren’t running!"
Beth 1-night trip
Posted less than an hour ago
Inn on the Square
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Lovely property. Would stay here again. Comfortable beds. Nice ambience in lobby. Great breakfast. Views at check in area beautiful. They have a little patio out front where u can sit and stare at the lake. There is a road between hotel and view of lake. Very peaceful there."
andrea 1-night trip
Posted 7 hours ago
Iris Hotel Cape Cod
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"This hotel was beautiful, clean and well located. And as a bonus had a heated outdoor pool that is open till October."
Tiffany 1-night trip
Posted 1 day ago
Hyannis Harbor Hotel
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"K"
Susan 2-night trip
Posted 1 day ago
Margaritaville Resort Cape Cod
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

8/10 Good
"room was beautiful and nice my only complaint was that the shampoo and conditioner and body wash was completely out!!"
emma 1-night trip
Posted 2 days ago
Hotel 1620 Plymouth Harbor

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