Find Winery Hotels in Chatham, MA from CA $148

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Check availability on Chatham Winery Hotels

Top Chatham Winery Hotels

Our top choices for Chatham hotels with winery

Copper Swan
WhiteCrest, 1 Queen Bed, Kitchenette | Private kitchenette

Copper Swan

3.0 star property
8.2 out of 10, Very good, (110)
"Brekkies was amazing too. Lovely staff. "
The price is CA $222
CA $254 total
includes taxes & fees
Sep 8 - Sep 9
Copper Swan
Uncommoner Hotel by Reverie Boutique Collection
View from room

Uncommoner Hotel by Reverie Boutique Collection

3.0 star property
9.4 out of 10, Exceptional, (31)
"Such a nice place to stay for a weekend getaway, we will definitely be back!"
The price is CA $204
CA $241 total
includes taxes & fees
Sep 14 - Sep 15
Uncommoner Hotel by Reverie Boutique Collection
Cape Cod Irish Village
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Cape Cod Irish Village

3.5 star property
6.4 out of 10, (1015)
"Great place "
The price is CA $195
CA $224 total
includes taxes & fees
Aug 24 - Aug 25
Cape Cod Irish Village
Chatham Wayside Inn
Beach nearby

Chatham Wayside Inn

4.0 star property
9.2 out of 10, Wonderful, (538)
"Great hotel"
The price is CA $373
CA $483 total
includes taxes & fees
Sep 1 - Sep 2
Chatham Wayside Inn
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Microwave, oven, stovetop, dishwasher

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

9.6 out of 10, Exceptional, (96)
"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. "
The price is CA $286
CA $782 total
includes taxes & fees
Sep 14 - Sep 15
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Kingfisher Harwich Port
Front of property

Kingfisher Harwich Port

3.0 star property
9.0 out of 10, Wonderful, (33)
"We had a wonderful stay ! The room was clean, comfortable, and well-maintained — everything we needed for a relax stay! "
The price is CA $311
CA $356 total
includes taxes & fees
Sep 7 - Sep 8
Kingfisher Harwich Port
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Fridge, microwave, oven, stovetop

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

8.8 out of 10, Excellent, (20)
"This is a beautiful cozy cottage, perfect for a small family. Centrally located on the Cape close to a lot of sights and attractions. There is a beach and restaurant within walking distance. My granddaughters and I had a great stay this summer."
The price is CA $148
CA $554 total
includes taxes & fees
Aug 24 - Aug 25
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
Smart TV, fireplace, books

Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach

10.0 out of 10, Exceptional, (15)
"So comfortable and clean!!! Owner is very communicative and this rates as one of my top Vrbo stays."
The price is CA $590
CA $1,224 total
includes taxes & fees
Sep 13 - Sep 14
Newly Renovated Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Outdoor dining

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

10.0 out of 10, Exceptional, (73)
"We had an amazing time in Wellfleet enjoying the beaches and this cottage. The location can’t be beat, and communication with our host was easy and pleasant. We’d love to come back!"
The price is CA $964
CA $1,615 total
includes taxes & fees
Sep 5 - Sep 6
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Newly Renovated Guest House For 10 Near The Beach!
Fridge, microwave, oven, stovetop

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (4)
"Space was great for our family/friends gathering Location perfect for events we were attending on the Cape"
The price is CA $712
CA $1,461 total
includes taxes & fees
Aug 26 - Aug 27
Newly Renovated Guest House For 10 Near The Beach!
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.

Top Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Great central location for Mid Cape. Great price. "
DANIEL 1-night trip
Posted 1 day ago
Cape Sands Inn