Winery Hotels & Resorts in Southeast Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on Southeast Massachusetts Winery Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Best Southeast Massachusetts Winery Hotels

Beach nearby
Chatham Wayside Inn
Chatham Wayside Inn
4.0 star property
9.2 out of 10, Wonderful, (577)
"Great hotel, great locatiion"
United States
Susan
Chatham Wayside Inn
Dining
Frederick William House
Frederick William House
3.5 star property
9.6 out of 10, Exceptional, (291)
"Beat B&B i have ever stayed at! "
United States
Philip
The price is NZ$309
includes taxes & fees
11 Nov - 12 Nov
Frederick William House
Garden
The Village Inn Cape Cod
The Village Inn Cape Cod
3.5 star property
10.0 out of 10, Exceptional, (221)
"It was so charming, would definitely stay there again! "
United States
Kyle
The price is NZ$336
includes taxes & fees
10 Nov - 11 Nov
The Village Inn Cape Cod
Suite, Balcony, Pool View
Hotel 1620 Plymouth Harbor
Hotel 1620 Plymouth Harbor
3.0 star property
8.2 out of 10, Very good, (1018)
"very clean, great staff!"
United States
Brenda
Hotel 1620 Plymouth Harbor
Front of property
The Inn on Onset Bay
The Inn on Onset Bay
2.5 star property
8.4 out of 10, Very good, (181)
"Great place to stay "
United States
Sandra
The price is NZ$175
includes taxes & fees
9 Nov - 10 Nov
The Inn on Onset Bay
View from room
Uncommoner Hotel by Reverie Boutique Collection
Uncommoner Hotel by Reverie Boutique Collection
3.0 star property
9.2 out of 10, Wonderful, (80)
"Great staff, beautiful property"
United States
Margaret
The price is NZ$261
includes taxes & fees
26 Oct - 27 Oct
Uncommoner Hotel by Reverie Boutique Collection
Front of property
Faraway Martha's Vineyard
Faraway Martha's Vineyard
3.5 star property
9.0 out of 10, Wonderful, (1008)
"Just a neat place to stay, very nice place. "
United States
Stuart
Faraway Martha's Vineyard
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
9.6 out of 10, Exceptional, (99)
"Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. "
United States
Mike D.
The price is NZ$712
includes taxes & fees
27 Oct - 28 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Exterior
Delano Homestead Bed & Breakfast
Delano Homestead Bed & Breakfast
3.0 star property
9.6 out of 10, Exceptional, (154)
"We loved staying here. We booked 1 night and stayed 2. The inn keepers are so kind and helpful and great to talk to. Would stay here again if in the area, every time!"
United States
Rona
The price is NZ$268
includes taxes & fees
12 Nov - 13 Nov
Delano Homestead Bed & Breakfast
Terrace/patio
Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street
Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street
8.8 out of 10, Excellent, (30)
"I’ve stayed here twice and have found it perfectly situated. Everything is well maintained. The bed was comfortable. I really enjoyed myself."
United States
Chad C.
The price is NZ$639
includes taxes & fees
28 Oct - 29 Oct
Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street
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.
View all properties

Top Southeast Massachusetts Hotel Reviews

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

10/10 Excellent
"Love this hotel. Love the staff. Very fun to go to with family and friends. My daughter’s favorite place to go to for weekend stays and Feb vacation! "
Lynden 1-night trip
Posted 14 hours ago
Hotel 1620 Plymouth Harbor

Explore a world of travel with Expedia