Title: Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=102119969&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) # Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! Bed & breakfast in Chester ## Photo gallery for Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ![Dining - Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! (Chester)](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/c51b349e.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Living area - Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! (Chester)](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/2e170eb4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! (Chester)](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/3195c3db.jpg?impolicy=resizecrop&rw=297&ra=fit) ![1 bedroom, iron/ironing board, WiFi, bed sheets - Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! (Chester)](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/abe9b83f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! (Chester)](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/223d62f8.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Rooms - Location - Policies Experience the charm of Chester Inn, a historic property on Main Street. Unwind in your private room with a smart TV, microwave, and mini fridge or relax in shared spaces with board games and coffee. Take advantage of free parking and proximity to hiking trails right behind the inn. ## Reviews 9.0 Wonderful ## Popular amenities - Air conditioning ## Room options ### Check availability for these dates Tonight [Dec. 10 - Dec. 11](https://www.expedia.ca/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Dec. 11 - Dec. 12](https://www.expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Dec. 12 - Dec. 14](https://www.expedia.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-14&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-14&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Dec. 19 - Dec. 21](https://www.expedia.ca/Hotel-Search?startDate=2025-12-19&endDate=2025-12-21&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-19&endDate=2025-12-21&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) ![Mod logo](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Sign in to view eligible discounts and perks. 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[Sign in](https://www.expedia.ca/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels-Historic-Chester-Inn-Circa.h102119969.Hotel-Information)[Sign up, it's free](https://www.expedia.ca/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels-Historic-Chester-Inn-Circa.h102119969.Hotel-Information) ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C43.26502%2C-72.59952&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=_PfW9mnpn_udBPEEFwNbt8_kBao=) Chester, VT #### What's nearby - DaVallia Art & Accents \- 2 min walk \- 0.2 km - Bonnie's Bundles Dolls \- 13 min walk \- 1.1 km - Okemo Mountain Resort \- 20 min drive \- 24.3 km - Stratton Mountain Resort \- 41 min drive \- 49.0 km - Killington Resort \- 43 min drive \- 56.3 km #### Getting around - Bellows Falls Station - 17 min drive - Springfield, VT (VSF-Hartness State) - 14 min drive #### Restaurants - ‪McDonald's - ‬13 min drive - ‪Country Girl Diner - ‬13 min walk - ‪Dunkin' - ‬14 min drive - ‪Southern Pie Cafe - ‬3 min walk - ‪Black Rock Steakhouse - ‬14 min drive ## About this property ### Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! Bed & breakfast located in Chester Depot Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! provides everything you need. Guests can connect to in-room WiFi. Additional perks include: - Smoke-free premises Room features All guestrooms at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! feature comforts such as air conditioning, as well as amenities like internet access. Extra amenities include: - Bathrooms with showers and hair dryers ## Similar properties ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Whimsical Room & Private Bathroom in Historic Inn Chester Depot - Kitchen - Free WiFi - Air conditioning - Outdoor space 8.8 Excellent 9 reviews CA $179 CA $281 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&selected=87135975&PinnedHotelID=87135975&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/a1626ba0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Room in Historic Inn! 20 Minutes to Okemo! Chester Depot - Air conditioning - Parking available - Toys/games - Kitchen 9.2 Wonderful 18 reviews CA $166 CA $267 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&selected=83938154&PinnedHotelID=83938154&HadPinnedHotel=true®ionId=-1&adults=2) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87135800/87135743/f57da4ca.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Honeymoon Suite with Jacuzzi Tub in Historic Inn Chester Depot - Free WiFi - Air conditioning - Parking available - Toys/games 8.6 Excellent 7 reviews CA $331 CA $478 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=87135743&PinnedHotelID=87135743&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/7656b8f3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### King & Queen Suite in Historic Inn Circa 1780 Chester Depot - Free WiFi - Air conditioning - Parking available - Kitchen 9.8 Exceptional 16 reviews CA $359 CA $527 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&selected=83938140&PinnedHotelID=83938140&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery Chester - Breakfast included - Parking included - Free WiFi - Air conditioning 9.2 Wonderful 107 reviews CA $272 CA $297 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&selected=87486236&PinnedHotelID=87486236&HadPinnedHotel=true®ionId=-1&adults=2) ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Fullerton Inn Chester Depot - Breakfast included - Parking included - Free WiFi - Restaurant 8.2 Very good 402 reviews CA $179 CA $195 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-15&endDate=2025-12-16&selected=15845368&PinnedHotelID=15845368&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/102000000/101650000/101640900/101640818/3316116c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Cairn, 1840s Cozy Stone Cottage, Pet Friendly Chester - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 18 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=101640818&PinnedHotelID=101640818&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22120300/22120284/w5261h3503x5y5-a5207a7e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! Chester Depot - Free WiFi - Parking available - Laundry - Microwave 9.4 Exceptional 39 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=22120284&PinnedHotelID=22120284&HadPinnedHotel=true®ionId=-1&adults=2) ![Restaurant](https://images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### COHO Inn & Motor Lodge Weston - Breakfast included - Parking included - Free WiFi - Bar 9.2 Wonderful 43 reviews CA $180 CA $197 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-16&endDate=2025-12-17&selected=104395732&PinnedHotelID=104395732&HadPinnedHotel=true®ionId=-1&adults=2) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/108320000/108315900/108315854/d9fba77b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Peaceful Brookside Getaway \~10 Mi to Okemo Slopes! Chester - Kitchen - Washer - Pet-friendly - Parking included 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-24&endDate=2025-12-25&selected=108315854&PinnedHotelID=108315854&HadPinnedHotel=true®ionId=-1&adults=2) ## Property amenities ### Internet - Available in all rooms: WiFi ### More - Smoking not allowed ## Room amenities ### Bedroom - Bedsheets provided ### Bathroom - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### More - Air conditioning - Heating - Iron/ironing board ## Policies ### Check-in Check-in time starts at 3:00 PM Minimum check-in age: 21 ### Check-out Check-out before 11:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## Frequently asked questions ### Is Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! pet-friendly? ### How much does it cost to stay at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? ### What time is check-in at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? ### What time is check-out at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? ### Where is Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Reviews ## Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! Reviews 9.0 ### Wonderful All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 9.0 Amenities ### 9.0 Staff & service ### 9.0 Eco-friendliness ### 10 Property conditions & facilities 10 - Excellent 1 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ## Reviews ### 8/10 Good #### Jacque Aug 19, 2024 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. ##### Jacque Stayed 1 night in Aug 2024 ### 10/10 Excellent #### Sharon Oct 6, 2025 Liked: Cleanliness, staff & service, amenities, property conditions & facilities Yes, wonderful location and stay ##### Sharon Stayed 1 night in Oct 2025 ## Expedia's Latest Trends ### Hotels > [Hotels near Monument Valley](https://www.expedia.ca/Monument-Valley-Hotels.d6351429.Travel-Guide-Hotels) > > [Pet-friendly Hotels in Northern Ontario](https://www.expedia.ca/Northern-Ontario-Hotels-Pet-Friendly-Hotel.0-0-d6057816-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) > > [Hilton Garden Inn Burlington Downtown](https://www.expedia.ca/Burlington-Hotels-Hilton-Garden-Inn-Burlington-Downtown.h9139549.Hotel-Information) > > [Hotel Vermont](https://www.expedia.ca/Burlington-Hotels-Hotel-Vermont.h6048522.Hotel-Information) > > [The Shore Club Turks and Caicos](https://www.expedia.ca/Providenciales-Hotels-The-Shore-Club-Turks-And-Caicos.h15438835.Hotel-Information) > > [Starlight Inn](https://www.expedia.ca/Burlington-Hotels-Starlight-Inn.h8409173.Hotel-Information) > > [Hotels in Dallas](https://www.expedia.ca/Dallas-Hotels.d178253.Travel-Guide-Hotels) > > [Hotels in Canning](https://www.expedia.ca/Canning-Hotels.d181842.Travel-Guide-Hotels) > > [Fairfield Inn by Marriott Burlington Williston](https://www.expedia.ca/Burlington-Hotels-Fairfield-Inn-By-Marriott-Burlington-Williston.h890405.Hotel-Information) > > [Conrad Tulum Riviera Maya](https://www.expedia.ca/Akumal-Hotels-Conrad-Tulum.h70501666.Hotel-Information) > > [Hotels in Tel Aviv](https://www.expedia.ca/Ben-Gurion-Airport-Hotels.0-aTLV-0.Travel-Guide-Filter-Hotels) > > [Occidental Aurelia](https://www.expedia.ca/Rome-Hotels-Occidental-Aurelia.h4107722.Hotel-Information) > > [Courtyard Marriott Burlington Harbor](https://www.expedia.ca/Burlington-Hotels-Courtyard-Marriott-Burlington-Harbor.h1513759.Hotel-Information) > > [Blind Tiger Burlington](https://www.expedia.ca/Burlington-Hotels-Willard-Street-Inn.h29481127.Hotel-Information) ### Flights > [Flights from Piarco (POS) to New York (JFK)](https://www.expedia.ca/lp/flights/pos/jfk/port-of-spain-to-new-york) > > [Flights from Pearson Intl. to MOW-All Airports](https://www.expedia.ca/lp/flights/yyz/mow/toronto-to-moscow) > > [Flights from Hamilton (YHM) to Arlanda (ARN)](https://www.expedia.ca/lp/flights/yhm/arn/hamilton-to-stockholm) > > [Flights from Windsor (YQG) to St. John's (YYT)](https://www.expedia.ca/lp/flights/yqg/yyt/windsor-to-st-johns) > > [IndiGo](https://www.expedia.ca/IndiGo-Flights.c6E.Travel-Guide-Airlines) > > [Flights from Toronto (YYZ) to Orlando (MCO)](https://www.expedia.ca/lp/flights/yyz/mco/toronto-to-orlando) ### Cruise ### Activities ### Packages > [Centreville Amusement Park](https://www.expedia.ca/Centreville-Amusement-Park-Old-Toronto.d6072471.Vacation-Attraction)