Find Winery Hotels in Brewster, MA

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

Check availability on Brewster Winery Hotels

This weekend
Next weekend

Top Brewster Winery Hotels

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
$456 nightly
The price is $521
Dec 2 - Dec 3
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Chatham Wayside Inn

4.0 star property
Chatham
9.2 out of 10, Wonderful, (595)
"We loved staying here! Our room was spacious, clean, quiet and very well maintained. The hotel is beautiful and a perfect location. "
United States
Beth
$174 nightly
The price is $199
Dec 2 - Dec 3
Total with taxes and fees
Chatham Wayside Inn

Uncommoner Hotel by Reverie Boutique Collection

3.0 star property
West Yarmouth
9.4 out of 10, Exceptional, (96)
"Great staff, beautiful property"
United States
Margaret
$102 nightly
The price is $117
Dec 4 - Dec 5
Total with taxes and fees
Uncommoner Hotel by Reverie Boutique Collection

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.
$357 nightly
The price is $408
Dec 2 - Dec 3
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
10.0 out of 10, Exceptional, (74)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
$379 nightly
The price is $433
Dec 2 - Dec 3
Total with taxes and fees
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

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 2 - Dec 3
Total with taxes and fees
The Village Inn Cape Cod

Quaint condo near private beach access with fireplace - close to dining

Dennis Port
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
$251 nightly
The price is $288
Dec 7 - Dec 8
Total with taxes and fees
Quaint condo near private beach access with fireplace - close to dining

Modern Beach & Pond Getaway; Heart of Cape Cod

South Yarmouth
10.0 out of 10, Exceptional, (11)
"Place was cozy and well stocked with all the household and bathroom items needed to make it a pleasant stay. Instructions were very clear and easy to follow from host. Host was responsive to requests as well."
United States
Philip R.
$471 nightly
The price is $539
Dec 10 - Dec 11
Total with taxes and fees
Modern Beach & Pond Getaway; Heart of Cape Cod

Cape Cod Irish Village

3.5 star property
Hyannis
6.4 out of 10, (1002)
"Plenty of parking space, walking distance to shops & restaurants."
United States
FLOR
$128 nightly
The price is $147
Dec 5 - Dec 6
Total with taxes and fees
Cape Cod Irish Village

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Chatham
8.6 out of 10, Excellent, (26)
"This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay."
United States
Jeffrey A.
$461 nightly
The price is $528
Dec 2 - Dec 3
Total with taxes and fees
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Top Brewster Hotel Reviews

Explore a world of travel with Expedia