Title: Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&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 ![Dining](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/c51b349e.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/3195c3db.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Living area](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/2e170eb4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/223d62f8.jpg?impolicy=resizecrop&rw=297&ra=fit) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/abe9b83f.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. 9.0 Wonderful ## Popular amenities - Air conditioning ## Room options ### Check availability for these dates Tonight [Nov. 28 - Nov. 29](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-29&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-29&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Nov. 29 - Nov. 30](https://www.expedia.ca/Hotel-Search?startDate=2025-11-29&endDate=2025-11-30&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-29&endDate=2025-11-30&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Nov. 28 - Nov. 30](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-28&endDate=2025-11-30&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Dec. 5 - Dec. 7](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-07&selected=102119969&PinnedHotelID=102119969&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-07&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 - ‪Chester 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 ![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 $181 CA $197 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-02&endDate=2025-12-03&selected=15845368&PinnedHotelID=15845368&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 $196 CA $305 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=87135743&PinnedHotelID=87135743&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 - Kitchen - Microwave 9.2 Wonderful 18 reviews CA $139 CA $234 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=83938154&PinnedHotelID=83938154&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 106 reviews CA $272 CA $297 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-02&endDate=2025-12-03&selected=87486236&PinnedHotelID=87486236&HadPinnedHotel=true®ionId=-1&adults=2) ![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 $139 CA $234 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=87135975&PinnedHotelID=87135975&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 $151 CA $165 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=104395732&PinnedHotelID=104395732&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/89000000/88940000/88933400/88933370/b26aecc3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area Chester - Kitchen - Pet-friendly - Free WiFi - Parking available 10 Exceptional 23 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-13&selected=88933370&PinnedHotelID=88933370&HadPinnedHotel=true®ionId=-1&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/108000000/107160000/107157400/107157394/389ff356.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful country cabin with hot tub and outdoor shower in Londonderry Londonderry - Kitchen - Pet-friendly - Air conditioning - Outdoor space 10 Exceptional 2 reviews CA $208 CA $511 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-02&endDate=2025-12-03&selected=107157394&PinnedHotelID=107157394&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/10000000/9720000/9715200/9715200/299bcb43.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Hartness House Springfield - Parking included - Free WiFi - Air conditioning 8.2 Very good 328 reviews CA $221 CA $244 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-29&endDate=2025-11-30&selected=9715200&PinnedHotelID=9715200&HadPinnedHotel=true®ionId=-1&adults=2) ![Exclusive Suite, Multiple Beds, Kitchenette, Mountain View](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Upper Pass Lodge at Magic Mountain Londonderry - Pool - Pet-friendly - Parking included - Free WiFi 8.2 Very good 686 reviews CA $140 CA $155 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&selected=1445790&PinnedHotelID=1445790&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? > No, pets are not allowed at this property. ### How much does it cost to stay at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? > As of Nov 28, 2025, prices found for a 1-night stay for 2 adults at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! on Nov 30, 2025 start from CA $124.83, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. [Choose your dates](https://www.expedia.ca/Chester-Hotels-Historic-Chester-Inn-Circa.h102119969.Hotel-Information?rfrr=HOT.HIS.question.link.click) for more accurate prices. ### What time is check-in at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? > Check-in begins at 3:00 PM. ### What time is check-out at Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! ? > Check-out is at 11:00 AM. ### Where is Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! located? > Located in Chester Depot, this bed & breakfast is within a 15-minute walk of DaVallia Art & Accents and Bonnie's Bundles Dolls. Vermont Country Store and My Minds Design are also within 9 mi (15 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## 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 ### 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 in San José](https://www.expedia.ca/San-Jose-Hotels.d603085.Travel-Guide-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 North Syracuse (SYR) to Nashville (BNA)](https://www.expedia.ca/lp/flights/syr/bna/syracuse-to-nashville) > > [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 > [Holland Zaandam Cruises](https://www.expedia.ca/Holland-America-Line-Zaandam.cHA-sAA.Cruise-Ship-Info) ### Activities > [Things to do in Barcelona](https://www.expedia.ca/Things-To-Do-In-Barcelona.d179992.Travel-Guide-Activities) ### Packages > [Hong Kong Island Vacations](https://www.expedia.ca/Hong-Kong-Island.d184245.Destination-Travel-Guides) > > [Centreville Amusement Park](https://www.expedia.ca/Centreville-Amusement-Park-Old-Toronto.d6072471.Vacation-Attraction)