Search Winery Hotels in Southeast Massachusetts

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Check availability on Southeast Massachusetts Winery Hotels

Our top choices for Southeast Massachusetts hotels with winery

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Chatham Wayside Inn

Chatham Wayside Inn

4.0 star property
Chatham
9.2 out of 10, Wonderful, (602)
"Super cozy and clean with fantastic staff and great location loved everyday spent here "
United States
noushin
Chatham Wayside Inn
Suite, Balcony, Pool View | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3.0 star property
Plymouth Downtown Waterfront District
8.2 out of 10, Very good, (1004)
"Great pool area for the kids"
United States
Rachel
Hotel 1620 Plymouth Harbor
Dining
Frederick William House

Frederick William House

3.5 star property
Falmouth
9.6 out of 10, Exceptional, (295)
"Beat B&B i have ever stayed at! "
United States
Philip
The price is ₹15,067
₹17,244 total
includes taxes & fees
15 Dec - 16 Dec
Frederick William House
View from room
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

3.0 star property
West Yarmouth
9.4 out of 10, Exceptional, (97)
"Hotel was quiet and very clean , pool water was cool"
United States
Robyn
The price is ₹9,542
₹10,921 total
includes taxes & fees
11 Dec - 12 Dec
Uncommoner Hotel by Reverie Boutique Collection
Garden
The Village Inn Cape Cod

The Village Inn Cape Cod

3.5 star property
Yarmouth Port
10.0 out of 10, Exceptional, (222)
"It was so charming, would definitely stay there again! "
United States
Kyle
The price is ₹15,224
₹17,423 total
includes taxes & fees
11 Dec - 12 Dec
The Village Inn Cape Cod
Exterior
Delano Homestead Bed & Breakfast

Delano Homestead Bed & Breakfast

3.0 star property
Fairhaven
9.6 out of 10, Exceptional, (157)
"Breakfast was great!"
United States
William
The price is ₹10,786
₹12,048 total
includes taxes & fees
21 Dec - 22 Dec
Delano Homestead Bed & Breakfast
Front of property
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 star property
Edgartown
9.0 out of 10, Wonderful, (1002)
"amazing stay"
United States
Cristi
Faraway Martha's Vineyard
Gazebo
Veranda Cape Cod Family Resort

Veranda Cape Cod Family Resort

2.5 star property
Bass River
9.2 out of 10, Wonderful, (262)
"Beautiful grounds, quiet and comfortable. Very well run. "
United States
Benita
The price is ₹16,124
₹18,454 total
includes taxes & fees
1 Jan - 2 Jan 2026
Veranda Cape Cod Family Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southeast Massachusetts Hotel Reviews

Falmouth Inn

Falmouth Inn

10/10 Excellent
"Clean room, amenities, indoor pool "
Inna 3-night trip
Posted 5 days ago
Falmouth Inn

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