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

[Chatham Travel Guide](https://expedia.ca/Chatham.dx10743)[Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d10743.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d10743.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.ca/Cheap-Flights-To-Chatham.d10743.Travel-Guide-Flights)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d10743.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d10743.Destination-Travel-Guides)

![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)

![](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Chatham Winery Hotels

Tonight

[Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2026-01-27&endDate=2026-01-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2026-02-06&endDate=2026-02-08&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/2000000/1520000/1517300/1517204/97707902.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)

![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)

### Chatham Wayside Inn

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

Chatham

9.2/10

Wonderful

(623 reviews)

"Yes, lovely place to stay."

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

Angela

CA $162

CA $245 total

includes taxes & fees

Jan 28 - Jan 29

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

![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)

![Exterior](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/e4387afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/f8355c29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Chatham

9.6/10

Exceptional

(102 reviews)

"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 $122

CA $576 total

includes taxes & fees

Jan 31 - Feb 1

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

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/c5925a50.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)

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

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

Chatham

8.6/10

Excellent

(26 reviews)

"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 $274

CA $745 total

includes taxes & fees

Jan 28 - Jan 29

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

![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/056f2544.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)

![Bicycling](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/6ac8a051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Voyager Escape King Elite](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/c366b6b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uncommoner Hotel by Reverie Boutique Collection

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

West Yarmouth

9.4/10

Exceptional

(103 reviews)

"Clean, nice staff, good amenities, central location"

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

Malbis

CA $161

CA $185 total

includes taxes & fees

Jan 30 - Jan 31

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

![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/ae47522f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/023eb077.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)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12430000/12426900/12426891/03e2796f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Village Inn Cape Cod

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

Yarmouth Port

10/10

Exceptional

(224 reviews)

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

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

Kyle

CA $212

CA $243 total

includes taxes & fees

Jan 28 - Jan 29

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

![Property grounds](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/f2fbf262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22970000/22960100/22960042/2d001dbd.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

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

Wellfleet

10/10

Exceptional

(77 reviews)

"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 $205

CA $616 total

includes taxes & fees

Jan 28 - Jan 29

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

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/c5192e69.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)

![Exterior](https://images.trvl-media.com/lodging/73000000/72440000/72435000/72434954/a7d1d86a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

West Brewster

9.6/10

Exceptional

(50 reviews)

"House was perfect for our family reunion! "

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

Gregg H.

CA $181

CA $734 total

includes taxes & fees

Jan 28 - Jan 29

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/ec7f5979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76670000/76664200/76664195/7b4a3afe.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)

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

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

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

South Yarmouth

10/10

Exceptional

(12 reviews)

"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"

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

Dennis S.

CA $215

CA $752 total

includes taxes & fees

Feb 1 - Feb 2

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

![Beach nearby](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/31cd0145.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)

![TV, fireplace](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/961738aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/76000000/75530000/75523600/75523575/fc910d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Dennis Port

9.0/10

Wonderful

(63 reviews)

"Very nice location and the unit was clean and comfortable. "

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

Jeanne M.

CA $82

CA $440 total

includes taxes & fees

Jan 28 - Jan 29

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

![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/c0db5e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/cf7f29f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/598d00d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69400000/69397500/69397439/74272731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

[](https://www.expedia.ca/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.Hotel-Information)

Harwich - Brewster Border

10/10

Exceptional

(6 reviews)

"Lovely property with attentive hosts "

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

marian t.

CA $888

CA $1,656 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Harwich-Hotels-Pond-Front-In-The-Woods.h69397439.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=2026-02-10&endDate=2026-02-11&regionId=10743&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Chatham Hotel Reviews

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

### Chatham Bars Inn

10/10 Excellent

"Beautiful property "

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

![Anchor In Distinctive Waterfront Lodging](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/7438dff7_y.jpg)

### Anchor In Distinctive Waterfront Lodging

10/10 Excellent

"Mary, at the front desk, was so extraordinarily kind- she was helpful and went out of her way to be kind. I enjoyed my stay there and felt like any question I had- or anything I needed- I could rely on Mary. She made my stay at the Anchor In- extra special "

[](https://expedia.ca/Hyannis-Hotels-Anchor-In-Distinctive-Waterfront-Lodging.h7640889.Hotel-Information)

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

### Bayside Resort Hotel

10/10 Excellent

"I will definitely recommend this resort to my friends. Excellent!"

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

![Hyannis Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg)

### Hyannis Plaza Hotel

10/10 Excellent

"The room was a spotless. Everything was clean. Very nice service. I love it. I would definitely stay again."

[](https://expedia.ca/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.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

"Evrything is so clean! We love staying here with our family with small children. The kids love it and so do we! We go back every year. It's become a tradition! "

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

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- [Luxury Hotels in North Chatham ](https://www.expedia.ca/North-Chatham-Hotels-Luxury-Hotel.0-0-d6285788-tLuxuryHotel.Travel-Guide-Filter-Hotels)
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- [Adults Only Resorts & in Salem ](https://www.expedia.ca/Salem-Hotels-Adults-Only-Resorts.0-0-d6600-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
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- [Boutique Hotels in West Chatham ](https://www.expedia.ca/West-Chatham-Hotels-Boutique-Hotel.0-0-d6285894-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
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- [Chatham Drama Guild ](https://www.expedia.ca/Chatham-Drama-Guild-Chatham.d6311758.Vacation-Attraction)
- [Hardings Lighthouse ](https://www.expedia.ca/Hardings-Lighthouse-West-Chatham.d6070173.Vacation-Attraction)
- [Monomoy Theatre ](https://www.expedia.ca/Monomoy-Theatre-Chatham.d6286898.Vacation-Attraction)
- [Visit North Chatham ](https://www.expedia.ca/North-Chatham.dx6285788)
- [Ridgevale Beach ](https://www.expedia.ca/Ridgevale-Beach-Massachusetts.d6287520.Vacation-Attraction)
- [Veterans Field ](https://www.expedia.ca/Veterans-Field-Chatham.d6070219.Vacation-Attraction)

- [Car rentals near Fox Hill ](https://www.expedia.ca/Car-Rentals-In-Fox-Hill.d553248621532666570.Car-Rental-Guide)

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