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

Winery Hotels & Resorts in Eastern Massachusetts from NZ$250

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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 library with bookshelves, a vase, and a table with chairs.
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.

1. 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 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 elevator with a control panel, a framed artwork above, and a wicker basket on the floor.

2. 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
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 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
NZ$496
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 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 stone pathway leading through a lush garden with dense foliage and a variety of plants.

4. 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 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.

5. Truro Beach Cottages

Truro Beach Cottages
North Truro
United States
Kate
NZ$307
includes taxes & fees
7 Oct - 8 Oct
Truro Beach Cottages
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A garden with a pergola structure, a pathway, and a seating area.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
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
NZ$441
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 staircase with wooden steps and a white wall. There is a white sofa with a geometric pillow in the living area.
A modern bathroom with a glass shower enclosure, a white sink, and a towel rack.
A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.

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 multi-story hotel with a modern architectural design, featuring a prominent entrance with a sign, landscaped gardens, and a well-maintained driveway.
A bedroom with a bed, nightstand, lamp, and white wardrobe.
A modern kitchen with light grey cabinets, stainless steel appliances, and a white dining table with chairs.
A modern hotel lobby with a round table, seating area, and large windows.

8. Luxury One Bedroom Condo (675S.F.)

Luxury One Bedroom Condo (675S.F.)
Plymouth Downtown Waterfront District
NZ$895
includes taxes & fees
1 Oct - 2 Oct
Luxury One Bedroom Condo (675S.F.)
A waterfront property with a large house, a sandy beach, and a person fishing.
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.
A marina with boats docked at wooden piers during sunset.

9. 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 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.

10. Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection
West Yarmouth
United States
Omar
NZ$250
includes taxes & fees
13 Oct - 14 Oct
Uncommoner Hotel by Reverie Boutique Collection
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Top Eastern Massachusetts Hotel Reviews

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