Title: Book the Best Chatham WINERY Hotels in 2026 | Expedia.ca

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![Chatham featuring a windmill, general coastal views and wild flowers](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Chatham, MA from CA $168

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## Check availability on Chatham Winery Hotels

Tonight

[Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chatham hotels with winery

![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/471fd6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/f436a6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chatham Wayside Inn

Chatham

9.2/10

Wonderful

(602)

"Super cozy and clean with fantastic staff and great location loved everyday spent here "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

noushin

[](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/bab152c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/d9225b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/7e1e24c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/49d1d00f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Chatham

9.6/10

Exceptional

(101)

"Our second year in a row staying here. Cute house and great location! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erin M.

CA $123

CA $564 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chatham-Hotels-Quaint-Chatham-Home-Wbeautiful-Backyard-Furnished-Multi-Level-Deck.h40283414.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/0a75a95f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/97bd2b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/9f2630b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/60d936ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Chatham

8.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey A.

CA $277

CA $729 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/76dbfadf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![VISIONARY KING ELITE](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/82541975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/10f6fac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/75730e05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uncommoner Hotel by Reverie Boutique Collection

West Yarmouth

9.4/10

Exceptional

(97)

"Hotel was quiet and very clean , pool water was cool"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robyn

CA $146

CA $168 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/00d26354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/1c660188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/2b1f0d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/6a955bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Village Inn Cape Cod

Yarmouth Port

10/10

Exceptional

(222)

"It was so charming, would definitely stay there again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kyle

CA $234

CA $267 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Yarmouth-Port-Hotels-The-Village-Inn-Cape-Cod.h12426891.Hotel-Information)

![Gazebo](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/cf5e1161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/c530c2ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/082cb655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, white sand](https://images.trvl-media.com/lodging/2000000/1190000/1181400/1181333/cf9e4214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Veranda Cape Cod Family Resort

Bass River

9.2/10

Wonderful

(262)

"Beautiful grounds, quiet and comfortable. Very well run. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Benita

CA $247

CA $283 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/South-Yarmouth-Hotels-Veranda-Cape-Cod-Family-Resort.h1181333.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/8928d372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a58600d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, books](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c100b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free internet, bed sheets](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/3e9866f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

West Brewster

9.6/10

Exceptional

(50)

"House was perfect for our family reunion! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gregg H.

CA $183

CA $717 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Brewster-Hotels-Cheery-House-Wdeck.h72434954.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/abe7cc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/43937c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/180-2a992e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/01e797f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Wellfleet

10/10

Exceptional

(75)

"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janice H.

CA $193

CA $600 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/South-Wellfleet-Hotels-Spectacular-Private-Waterfront-Cottage-On-Bayside-Panoramic-Views-Pet-Friendly.h22960042.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/728a4339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/3bdd02f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/d8a1ebdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/6d5b6832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Beach & Pond Getaway; Heart of Cape Cod

South Yarmouth

10/10

Exceptional

(12)

"Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin B.

CA $223

CA $766 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/South-Yarmouth-Hotels-Homey-Central-Vacay-W-Game-Room-Near-Beach-And-Pond.h76664195.Hotel-Information)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/77bb82da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/eadc4fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/592ba5e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/89d3eb8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Dennis Port

9.0/10

Wonderful

(62)

"Clean, beautiful, great location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer B.

CA $83

CA $394 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Dennis-Port-Hotels-Quaint-Condo-Near-Private-Beach-Access-With-Fireplace-Close-To-Dining.h75523575.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24&regionId=10743&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Chatham Hotel Reviews

![Hyannis Travel Inn](https://images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg)

### Hyannis Travel Inn

10/10 Excellent

"Perfect location to walk everywhere. Clean rooms. Very professional and courteous staff"

[](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information)

![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg)

### Margaritaville Resort Cape Cod

10/10 Excellent

"The entire place was spotless and rooom beet pleasant. Staff was super friendly and the Landshark Bar was excellent. Highly recommend a stay here ! "

[](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information)

![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg)

### Bayside Resort Hotel

10/10 Excellent

"Nice and clean, friendly receptionist. Pool is great, amusement arcade good for kids. Reasonable rates and location on the main road through West Yarmouth. Nicely lit up for Christmas. Back area looks on to lagoon and has a fire pit and sand"

[](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information)

![Cape Sands Inn](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg)

### Cape Sands Inn

10/10 Excellent

"Clean room, great rate easy checkin and easy checkout. Will stay again. "

[](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information)

![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg)

### Chatham Bars Inn

10/10 Excellent

"Great accommodation and staff."

[](https://expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information)

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- [Ridgevale Beach ](https://www.expedia.ca/Ridgevale-Beach-Massachusetts.d6287520.Vacation-Attraction)
- [Veterans Field ](https://www.expedia.ca/Veterans-Field-Chatham.d6070219.Vacation-Attraction)

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