Find 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

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (603)
"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 drapes
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, (1006)
"Great pool area for the kids"
United States
Rachel
Hotel 1620 Plymouth Harbor
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 NT$5,272
NT$6,034 total
includes taxes & fees
Dec 16 - Dec 17
The Village Inn Cape Cod
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 NT$3,304
NT$3,782 total
includes taxes & fees
Dec 21 - Dec 22
Uncommoner Hotel by Reverie Boutique Collection
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 NT$3,743
NT$4,181 total
includes taxes & fees
Dec 16 - Dec 17
Delano Homestead Bed & Breakfast
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 NT$5,584
NT$6,390 total
includes taxes & fees
Jan 1 - 2026/1/2
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

Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Helpful staff & food & drinks were great ! "
glen 1-night trip
Posted 3 days ago
Chatham Bars Inn

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