A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Search Winery Hotels in Eastern 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 availability on Eastern 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 Eastern Massachusetts hotels with winery

A cozy lounge area with leather sofas, striped armchairs, a fireplace, and a bookshelf.
A hotel room with a large bed, two bedside tables, a nightstand, a lamp, a ceiling light fixture, a window with curtains, and framed artwork on the walls.
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.

1. The Drew Hotel

The Drew Hotel
Plymouth Downtown Waterfront District
United States
Robert
₹18,788
₹20,986 total
includes taxes & fees
6 Oct - 7 Oct
The Drew Hotel
A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.
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.
A modern kitchen with a central island, built-in appliances, and wicker chairs.

2. 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
A two-story house with a stone facade, a balcony, and a well-maintained garden.
A garden patio with stone steps, a table and chairs, and a large umbrella.
A room with a large window, a dining table with a tablecloth, and a chair with a cushion.
A coastal landscape with a sandy beach and grassy dunes.

3. 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 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.

4. 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 row of mobile homes with gravel driveways, each with a small front porch and potted plants.
A spacious living room with a high ceiling, a dining area with a view, and a kitchen with white cabinets.
A bedroom with two beds, a window, and a sign on the wall.
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

5. Truro Beach Cottages

Truro Beach Cottages
North Truro
United States
Kate
₹14,599
₹16,709 total
includes taxes & fees
8 Oct - 9 Oct
Truro Beach Cottages
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.

6. 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 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 modern bathroom with a glass shower enclosure, a white sink, and a towel rack.
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
₹22,041
₹25,226 total
includes taxes & fees
7 Oct - 8 Oct
Kingfisher Harwich Port
A poolside area with a wooden pergola, green seating, and a sign reading "LE JARDIN BLEU".
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 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.

8. 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
View all properties

Top Eastern Massachusetts Hotel Reviews

Explore a world of travel with Expedia