Find Winery Hotels in Southeast Massachusetts

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Top Southeast Massachusetts Winery Hotels

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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
$214 nightly
The price is $245
Dec 23 - Dec 24
Total with taxes and fees
Chatham Wayside Inn
Suite, Balcony, Pool View | Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
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
$179 nightly
The price is $200
Dec 10 - Dec 11
Total with taxes and fees
Hotel 1620 Plymouth Harbor
Dining
Frederick William House

Frederick William House

3.5 star property
Falmouth
9.6 out of 10, Exceptional, (294)
"Beat B&B i have ever stayed at! "
United States
Philip
$169 nightly
The price is $193
Dec 10 - Dec 11
Total with taxes and fees
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
$106 nightly
The price is $121
Dec 10 - Dec 11
Total with taxes and fees
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
$169 nightly
The price is $193
Dec 10 - Dec 11
Total with taxes and fees
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
$120 nightly
The price is $134
Dec 11 - Dec 12
Total with taxes and fees
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
$226 nightly
The price is $252
Dec 14 - Dec 15
Total with taxes and fees
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
$179 nightly
The price is $205
Jan 1 - Jan 2, 2026
Total with taxes and fees
Veranda Cape Cod Family Resort
Property grounds
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.
$350 nightly
The price is $391
Dec 10 - Dec 11
Total with taxes and fees
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

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.
$356 nightly
The price is $407
Dec 14 - Dec 15
Total with taxes and fees
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

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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