Title: Book the Best HISTORIC Hotels in Chatham 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)

![](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 Historic Hotels

Tonight

[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)

Tomorrow

[Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2026-01-28&endDate=2026-01-29&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 historic hotels

![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)

![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)

![Exterior](https://images.trvl-media.com/lodging/41000000/40290000/40283500/40283414/e4387afe.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

Feb 2 - Feb 3

[](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)

![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)

![TV, books](https://images.trvl-media.com/lodging/56000000/55590000/55584200/55584101/97bd2b9b.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)

### 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 $746 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Chatham-Hotels-Beautiful.h55584101.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/c100b426.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)

![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 30 - Jan 31

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/58000000/57120000/57119600/57119600/w1242h889x0y0-ba5cd960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/58000000/57120000/57119600/57119600/w3805h3024x227y0-19b5052c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/58000000/57120000/57119600/57119600/797729b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57120000/57119600/57119600/8311230c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

[](https://www.expedia.ca/Dennis-Port-Hotels-Walk-To-DennisPort-Beaches-4-MinBars-And-Restaurants-2min-WalkPerfect-Location.h57119600.Hotel-Information)

Dennis

10/10

Exceptional

(32 reviews)

"The place was adorable and the location was perfect. We could walk to the beach, to an amazing little bakery and it gave us great access to our weekend of wedding events.Irene had suggested sunset at Mayflower Beach and it was spectacular. We will be back in the future."

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

Natalie D.

CA $411

CA $950 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Dennis-Port-Hotels-Walk-To-DennisPort-Beaches-4-MinBars-And-Restaurants-2min-WalkPerfect-Location.h57119600.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&specialized_stays_group_explore=historic_property&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)

![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg)

### Chatham Wayside Inn

10/10 Excellent

"Yes, I was upgraded. Staff was wonderful. "

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

![The Mansion at Ocean Edge](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52_y.jpg)

### The Mansion at Ocean Edge

10/10 Excellent

"Didnt overlook beach."

[](https://expedia.ca/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.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)

![Captain's House Inn](https://images.trvl-media.com/lodging/3000000/2830000/2824300/2824230/c5cf48fc_y.jpg)

### Captain's House Inn

10/10 Excellent

"Great place to stay in Chatham. Went for First Night celebrations and the Inn was clean and comfortable and served one of the best breakfasts! Highly recommend!"

[](https://expedia.ca/Chatham-Hotels-Captains-House-Inn.h2824230.Hotel-Information)

![Holiday Inn Hyannis by IHG](https://images.trvl-media.com/lodging/1000000/20000/12500/12477/6128ed99_y.jpg)

### Holiday Inn Hyannis by IHG

10/10 Excellent

"Check in was easy and the front desk person was wonderful. "

[](https://expedia.ca/Hyannis-Hotels-Holiday-Inn-Hyannis-By-IHG.h12477.Hotel-Information)

## Frequently asked questions

### What should I expect on my historical trip to Chatham?

### How many historically relevant hotels will I find in Chatham?

### What are the must-see historical sites and other places to visit in Chatham?

### What is a historic hotel like in Chatham?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Chatham have modern facilities?

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