A lake surrounded by autumn-colored trees.

Search Winery Hotels in Southeast Massachusetts

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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 park with a wooden staircase, lush greenery, and blooming pink flowers.
A coastal landscape with a sandy beach and grassy dunes.
A garden patio with stone steps, a table and chairs, and a large umbrella.

1. Frederick William House

Frederick William House
Falmouth
United States
David
₹23,434
₹26,820 total
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 room with a dark brown wall, a black leather sofa, a wooden dining table with chairs, a lamp, and framed pictures.
A library with bookshelves, a vase, and a table with chairs.

2. The Drew Hotel

The Drew Hotel
Plymouth Downtown Waterfront District
United States
Robert
₹18,284
₹20,424 total
includes taxes & fees
5 Oct - 6 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 room with a fireplace, a dining table, and a white sofa.
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
₹21,117
₹23,587 total
includes taxes & fees
8 Oct - 9 Oct
Delano Homestead Bed & Breakfast
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 row of white bicycles with brown seats and wicker baskets, parked in front of a white building with black railings and large windows.
A bartender pouring a drink into a gold cocktail shaker.

4. Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection
West Yarmouth
United States
Omar
₹11,403
₹13,507 total
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 spacious living room with a sofa, chairs, a coffee table, and a bookshelf filled with decorative items.

5. Faraway Martha's Vineyard

Faraway Martha's Vineyard
Edgartown
United States
Thomas
₹26,348
₹30,903 total
includes taxes & fees
29 Oct - 30 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 modern bathroom with a glass shower enclosure, a white sink, and a towel rack.
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.

6. Kingfisher Harwich Port

Kingfisher Harwich Port
Harwich Port
United States
Marc
₹22,041
₹25,226 total
includes taxes & fees
7 Oct - 8 Oct
Kingfisher Harwich Port
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
A living room with wicker furniture, a fireplace, and a staircase.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

7. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
Canada
Ashley
₹17,191
₹23,850 total
includes taxes & fees
29 Oct - 30 Oct
Chatham Wayside Inn
A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.
A modern kitchen with a central island, built-in appliances, and wicker chairs.
A storefront with a sign reading "SEA BAGS" and a chalkboard sign advertising handmade totes and accessories.
A waterfront hotel with outdoor seating and a view of the marina.

8. Thomas Sea Suites

Thomas Sea Suites
Plymouth Downtown Waterfront District
United States
Heather
₹32,973
₹41,150 total
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 1 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 8 hours ago
Iris Hotel Cape Cod
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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