Title: Book the Best Chester Hotels with FREE PARKING in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) ![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Chester, VT from CA $142 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Hotels with Free Parking Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-08&endDate=2025-11-09&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-09&endDate=2025-11-10&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Hotels with Free Parking ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (916) "The room was very clean, and both staff and service were outstanding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wonji CA $129 CA $142 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/4ee226d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/44151c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c0073409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bromley View Inn Bondville 9.0/10 Wonderful (399) "Breakfast , beverages and hot tub were nice in addition to the family game room area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/32bcc2b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/9ca0f525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (723) "Check in was easy and there is coffee available 24 hours a day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $148 CA $163 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/78c81c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/c887af2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullerton Inn Chester Depot 8.2/10 Very good (400) "A unique inn in a charming town. Breakfast falls short, but staff is friendly and helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dominique CA $181 CA $197 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/ae105a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/0f0b56c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Garden View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/20cd6ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (105) "Room was super quiet and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ernest CA $262 CA $286 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/211acecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/5e6bf716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel Keene 8.4/10 Very good (945) "Room was clean and staff was friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Britney CA $166 CA $180 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/ac65fd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/c828df52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel Springfield 8.8/10 Excellent (798) "so clean and friendly it was a perfect stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colette CA $202 CA $222 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/907a3236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/89435dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Putney Inn Putney 8.4/10 Very good (1001) "Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MICHAEL CA $129 CA $142 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2744f7ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/707e42f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2680e185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1007) "Friendly, efficient staff and a very clean and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $199 CA $219 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Exclusive Room | Living area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/7573dd00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/730277ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/ea836d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/f95851fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Columns Inn Newfane 9.6/10 Exceptional (9) "Cozy inn in a beautiful setting, and great staff and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Archith CA $222 CA $243 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.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=2025-11-22&endDate=2025-11-23®ionId=89014&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "N " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great place to stay" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](//images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Wonderful Staff!" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Front desk woman excellent " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "We loved this hotel as everything was very clean. The staff was very friendly and helpful. They provided us with information as to other areas or places we could go with our family. They were very informative. And they do provide just about everything you need." [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Excellent. Most folks were friendly and would smile. Front desk seemed to being having some rough days. :( But still a great stay. " [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "The staff were so welcoming and friendly! When we got engaged they all cheered for us and were so sweet!" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Friendly staff. Unique stay. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ## Frequently asked questions ### Are there any hotels in Chester with parking? > The [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) is a charming 3-star hotel that not only offers free self-parking but also boasts stunning mountain views. With a remarkable traveller rating of 9.2, guests rave about the delicious breakfast and the excellent hospitality, making it a delightful choice for families seeking both comfort and convenience. > > > > Another great option is the [Fullerton Inn](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information), which also provides complimentary self-parking. With a rating of 8.2, guests appreciate the cozy, clean rooms and the friendly staff. The inn's restaurant is known for its delicious food, adding to the overall positive experience. > > > > For those who prefer a more unique stay, the [King & Queen Suite in Historic Inn Circa 1780](https://www.expedia.ca/Chester-Hotels-King-Queen-Suite-In-Historic-Inn-Circa-1780.h83938140.Hotel-Information) offers a lovely kitchen and a picturesque porch, making it superb for families looking to enjoy a cozy feel. This suite has an impressive traveller rating of 9.8, and guests have mentioned the good quality coffee as a delightful perk. > > > > Additionally, the [Motel in the Meadow](https://www.expedia.ca/Chester-Hotels-Motel-In-The-Meadow.h14724639.Hotel-Information) welcomes pets at no extra charge and features free parking, alongside a review score of 8.4. This could be a wonderful choice for families travelling with pets, seeking both affordability and comfort. ### Are there Chester hotels that offer free parking? > If you're looking for hotels in Chester that offer free parking, the [Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) is a wonderful option to consider. This charming 3-star inn boasts a stellar review rating of 9.2, where travellers rave about the delicious breakfast and the comfortable, clean rooms. Nestled in a beautiful location, it offers stunning mountain views and is conveniently close to mountain biking and climbing activities, making it great for adventure-seeking families. > > > > Another great choice is the [Fullerton Inn](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information), which has a rating of 8.2. Guests appreciate the cozy, clean rooms and the friendly, helpful staff. The inn also serves a delightful continental breakfast and features a lovely restaurant on-site. Plus, with its free self-parking, it provides added convenience for those travelling with children or pets. > > > > Don't overlook the [Motel in the Meadow](https://www.expedia.ca/Chester-Hotels-Motel-In-The-Meadow.h14724639.Hotel-Information), either. With an excellent review score of 8.4, this motel offers both free WiFi and breakfast options, making it an excellent value for families. It welcomes pets at no extra charge and ensures a straightforward stay with complimentary self-parking. ### How much does a hotel with parking in Chester typically cost? > Enjoy staying in a hotel in Chester with parking, with plenty of hotels from CA $142 offering incredible amenities. Be sure to book in advance to explore more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays. Prices can vary depending on the area, season, and hotel amenities. ### Which area of Chester is best to stay in for convenient parking? > The charming village of Chester, Vermont, is an excellent choice for travellers seeking convenience and comfort, particularly when it comes to parking. This picturesque area is known for its historic architecture and friendly atmosphere, making it easy to explore on foot. With ample off-street parking options available, visitors can enjoy the quaint shops and delightful eateries without the hassle of searching for a spot. > > > > For families, staying near the town centre is particularly advantageous. This area not only provides easy access to local attractions like the historic Chester Village Green and the nearby Okemo Mountain Resort, but it also ensures a relaxed environment where children can roam freely. Parks and playgrounds are within walking distance, making it a superb base for family adventures. > > > > Couples may find the scenic outskirts of Chester to be an enchanting retreat. With beautiful landscapes and serene surroundings, this area offers romantic accommodations, where you can unwind after a day of exploring. The proximity to hiking trails and local wineries allows for intimate outings, while still providing convenient parking for ease of access. ### What are the best hotels in Chester with electric vehicle charging stations? > The Beautiful Farmhouse in Historic Village is an excellent option for travellers seeking a charming stay in Chester, Vermont. This delightful property not only features electric vehicle charging stations but also offers stunning mountain views that enhance its picturesque setting. > > > > Families will appreciate the thoughtful amenities designed for children, including a shared outdoor play area, toys, books, and games that will keep the little ones entertained. The farmhouse is well-equipped with a kitchen for convenient meal preparation, alongside a comfortable sofa bed for extra sleeping arrangements. With a remarkable review rating of 9.2, guests consistently praise the warm atmosphere and the welcoming environment for families. ### How can I save on a hotel with parking in Chester with Expedia? > There are plenty of ways to save on a hotel with parking in Chester. Join [One Key™](https://www.expedia.ca/welcome-one-key)—Expedia's free travel rewards program—to unlock discounted prices across a range of top hotels. Another tip is to book in advance as this will often help you secure a cheaper rate. But, if you're feeling spontaneous, be sure to check for last-minute deals. ### Can I cancel my hotel reservation on Expedia? > If your plans change, it's easy to cancel your hotel with free cancellation on Expedia. Just use the "Fully refundable property" filter during your search to find the right hotel in Chester with parking. 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