Winery Hotels & Resorts in Southeast Massachusetts from NZ$210

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Check availability on Southeast Massachusetts Winery Hotels

Our top choices for Southeast Massachusetts hotels with winery

Beach nearby
Chatham Wayside Inn

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
Hotel 1620 Plymouth Harbor

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

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 NZ$332
includes taxes & fees
14 Dec - 15 Dec
Frederick William House
View from room
Uncommoner Hotel by Reverie Boutique Collection

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 NZ$210
includes taxes & fees
11 Dec - 12 Dec
Uncommoner Hotel by Reverie Boutique Collection
Garden
The Village Inn Cape Cod

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 NZ$335
includes taxes & fees
11 Dec - 12 Dec
The Village Inn Cape Cod
Exterior
Delano Homestead Bed & Breakfast

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 NZ$232
includes taxes & fees
11 Dec - 12 Dec
Delano Homestead Bed & Breakfast
Front of property
Faraway Martha's Vineyard

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

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 NZ$354
includes taxes & fees
6 Jan - 7 Jan 2026
Veranda Cape Cod Family Resort
Property grounds
Big Sandy Beachcomber

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
9.6 out of 10, Exceptional, (12)
"Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!"
United States
Ben L.
The price is NZ$677
includes taxes & fees
17 Dec - 18 Dec
Big Sandy Beachcomber
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (101)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$705
includes taxes & fees
14 Dec - 15 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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

Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"Very cute and quaint. Spectacular hostess and very accommodating"
JEANNETTE 4-night trip
Posted 2 days ago
Faraway Martha's Vineyard

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