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

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Check availability on Eastern Massachusetts Winery Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 bathroom with a marble sink, a white toilet, and a shower area.

1. The Drew Hotel

The Drew Hotel
Plymouth Downtown Waterfront District
United States
Robert
£153
includes taxes & fees
1 Nov - 2 Nov
The Drew Hotel
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 garden with a pergola structure, a pathway, and a seating area.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

2. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
Canada
Ashley
£188
includes taxes & fees
1 Nov - 2 Nov
Chatham Wayside Inn
A two-story house with a stone facade, a balcony, and a well-maintained garden.
A coastal landscape with a sandy beach and grassy dunes.
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.

3. Frederick William House

Frederick William House
Falmouth
United States
David
£137
includes taxes & fees
1 Nov - 2 Nov
Frederick William House
A row of mobile homes with gravel driveways, each with a small front porch and potted plants.
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.
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.

4. Truro Beach Cottages

Truro Beach Cottages
North Truro
United States
Kate
£139
includes taxes & fees
7 Oct - 8 Oct
Truro Beach Cottages
A two-story house with a front porch, a stone wall, and a well-maintained garden.
A pathway leading to a house with a stone wall, a white bench, and a gate.
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.

5. Delano Homestead Bed & Breakfast

Delano Homestead Bed & Breakfast
Fairhaven
United States
Michael
£127
includes taxes & fees
1 Nov - 2 Nov
Delano Homestead Bed & Breakfast
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.
A spacious lobby with a reception desk, a large sofa, and a chandelier.
A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.
A spacious living room with a sofa, chairs, a coffee table, and a bookshelf filled with decorative items.

6. Faraway Martha's Vineyard

Faraway Martha's Vineyard
Edgartown
United States
Thomas
£207
includes taxes & fees
1 Nov - 2 Nov
Faraway Martha's Vineyard
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 bar area with a patterned wall, wicker chairs, and a tiled floor.
A row of white bicycles with brown seats and wicker baskets, parked in front of a white building with black railings and large windows.

7. Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection
West Yarmouth
United States
Melissa
£103
includes taxes & fees
1 Nov - 2 Nov
Uncommoner Hotel by Reverie Boutique Collection
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
£321
includes taxes & fees
15 Oct - 16 Oct
Thomas Sea Suites
A wooden pier leading to a beach with a clear sky.
A balcony with a view of a forested landscape and hills.
A covered swimming pool with lounge chairs and a table, surrounded by a wooden deck and glass doors.
A beachside building with a wooden deck and a staircase leading to an upper level.

9. Blue Sea Motor Inn

Blue Sea Motor Inn
North Truro
United States
Richard
£105
includes taxes & fees
7 Oct - 8 Oct
Blue Sea Motor Inn
A coffee station with a display case of pastries and a beverage dispenser.
A hotel hallway with wooden paneling, framed artwork on the walls, a reception desk with a vase of flowers, and a carpeted floor.
A lobby with a reception desk, a staircase, leather chairs, a coffee table, and a framed picture on the wall.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a window with curtains.

10. Four Points by Sheraton Boston Logan Airport Revere

Four Points by Sheraton Boston Logan Airport Revere
Revere
United States
Margaret
£125
includes taxes & fees
1 Nov - 2 Nov
Four Points by Sheraton Boston Logan Airport Revere
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Top Eastern Massachusetts Hotel Reviews

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

8/10 Good
"This was a great location for a solo traveler walking around the city. There is construction next door which goes on 24/7 and all you hear at night is pounding. I’m sure it won’t last forever however for the time being it could be an issue for some."
Lisa 3-night trip
Posted 8 hours ago
Wyndham Boston Beacon Hill

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