Title: 4 Stars Hotels in Chester, Vermont from CA $203 - Find Cheap Chester Hotels With 4 Stars | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx89014)[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)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d89014.Travel-Guide-Flights)[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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Chester, Vermont from CA $203 ![](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 4 Star Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-16&endDate=2025-10-17&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester 4 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddae827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/4b2f1194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa Manchester 7.4/10 Good (550) "Beautiful hotel! " CA $142 CA $230 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/2ed69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort Woodstock 9.2/10 Wonderful (538) "Beautiful hotel!! The staff, room, and spa were fantastic!!" CA $490 CA $601 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/55f5385b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/1702fe64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/a88566dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kimpton Taconic Hotel by IHG Manchester 9.4/10 Exceptional (808) "Very nice, beautiful inn" CA $220 CA $296 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![Family Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/e090e64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/125b9e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/29250062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn West Woodstock 9.4/10 Exceptional (1001) "Great location, very quiet with good breakfast choices. " CA $252 CA $328 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson West Woodstock 9.8/10 Exceptional (237) "Excellent Vintage style B&B. " CA $184 CA $203 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Deluxe Room](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/8359157a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/c0e37122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/190c1179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/b891aa86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reluctant Panther Inn and Restaurant Manchester 9.8/10 Exceptional (315) "Helpful staff amazing grounds/property lovely rooms and great breakfasts delivered in baskets" CA $289 CA $318 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/ad9a6e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Garden View | Living area](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/074a9a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/aa061d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Weathersfield Perkinsville 9.8/10 Exceptional (66) "Comfortable room and tasty dinner. Very well run." CA $280 CA $357 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) ![Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/f168cf38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cottage | Private kitchen](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/8785d8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b590c7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/6bc4601c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windham Hill Inn West Townshend 8.4/10 Very good (36) "This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. " CA $255 CA $278 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/065183a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/773ceea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 9](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/1cc60990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 3](https://images.trvl-media.com/lodging/20000000/19540000/19532700/19532700/2ed1bc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Village Inn of Woodstock Woodstock 9.6/10 Exceptional (94) "Super clean and the ambiance was so perfect for such a neat place. Owners are awesome!" [](https://www.expedia.ca/Woodstock-Hotels-The-Village-Inn-Of-Woodstock.h19532700.Hotel-Information) ![Solitude Village Two Bedroom Suite Mountainside | Private kitchen](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/676d662f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 6 Bedrooms (Home) | Living area](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/a005759a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Solitude Village One Bedroom Penthouse | Living area](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/a4732d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/w5264h3508x0y0-08cf438b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Solitude Village at Okemo Clock Tower Base Area 8.0/10 Very good (31) "Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also." [](https://www.expedia.ca/Ludlow-Hotels-Solitude-Village-At-Okemo.h12521237.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun and Moon Room](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/40986f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on Putney Road Brattleboro 9.8/10 Exceptional (55) "Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries." CA $375 CA $412 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/64a51502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winter Place Two Bedroom plus Loft Ski In/Out](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/6a064e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/f3eda008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/3cf7aa32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winterplace at Okemo Clock Tower Base Area 8.8/10 Excellent (24) "I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place " [](https://www.expedia.ca/Ludlow-Hotels-Winterplace-At-Okemo.h12522689.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/8d4d123d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/ac294149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms (Meadow) | Terrace/patio](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/b4207cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920085/eb5b0456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Equinox Resort Residences Manchester 8.0/10 Very good (2) "The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. " CA $1,023 CA $1,474 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Equinox-Resort-Residences.h99920085.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/925c9630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/a49a5b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/99ee403a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31710000/31708400/31708312/beb3eeb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seesaw's Lodge Peru 10/10 Exceptional (24) "Beautiful lodge, the staff are so helpful and friendly. The rooms are really nice and cozy. will stay here again." CA $249 CA $272 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Bennington-Hotels-Seesaws-Lodge.h31708312.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/a23bd7ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, minibar](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/d4a96b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/cea1ec7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/7179648d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesterfield Inn West Chesterfield 9.0/10 Wonderful (104) "Great stay" CA $423 CA $459 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/66d1371a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed | View from room](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/b17b46be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/c2bef1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 1 King Bed | Living area](https://images.trvl-media.com/lodging/26000000/25080000/25079500/25079404/abbab27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Woodstocker B&B Woodstock 10/10 Exceptional (51) "This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! " [](https://www.expedia.ca/Woodstock-Hotels-The-Woodstocker-BB.h25079404.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/a85c8ad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/726c249b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/453cecd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coldbrook Two Doubles](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/5c9dc85d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hermitage Inn Vermont West Dover 9.2/10 Wonderful (15) "Great stay,beautiful property!" CA $626 CA $689 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/West-Dover-Hotels-The-Hermitage-Inn-Vermont.h74248370.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/84000000/83090000/83087000/83086930/e1d2b1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serenity Suite](https://images.trvl-media.com/lodging/84000000/83090000/83087000/83086930/31589c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/84000000/83090000/83087000/83086930/4a2c573b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/84000000/83090000/83087000/83086930/e46c8989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brattleboro Brattleboro 10/10 Exceptional (5) "Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. " [](https://www.expedia.ca/Brattleboro-Hotels-The-Brattleboro.h83086930.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/ccb1644d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/33b62d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/32e0239c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71820000/71814900/71814822/00f4360c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4+BR pet-friendly w/ hot tub & Stratton parking pass! Winhall [](https://www.expedia.ca/Bondville-Hotels-4BR-Pet-Friendly-W-Hot-Tub-Stratton-Parking.h71814822.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/5fe23c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/e76d85b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/22ad6b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/6ee6a37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deer Brook Inn Woodstock 10/10 Exceptional (21) "One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!" [](https://www.expedia.ca/Woodstock-Hotels-Deer-Brook-Inn.h1482698.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d89014.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d89014.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester. ![The Weston](https://images.trvl-media.com/lodging/101000000/100710000/100702800/100702715/5fa05705_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Weston 630 Main St, Weston, VT CA $557 CA $608 total Oct 22 - Oct 23 includes taxes & fees 10/10 Exceptional! (8 reviews) [](https://expedia.ca/Weston-Hotels-The-Weston.h100702715.Hotel-Information) Still don't see what you're looking for? [See all properties in Chester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=89014&star=40&star=40&amenities=WATER_PARK) 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. ## Top Chester Hotel Reviews ![Kimpton Taconic Hotel by IHG](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "The is was our first trip to Manchester. What a great town! The hotel was lovely- easy parking, quiet, and quaint. The staff at the front desk were so helpful ! You could walk to town but it would be about a 20 min adventure… make sure you go to the North field book store~ wonderful!! And we had coffee and egg sandwich at their coffee shop around the corner." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ## Find out more about Chester If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Vermont, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Chester? > To book a 4-star hotel in Chester that fits your budget, take advantage of Expedia's filter tool. Check out the availability during your chosen dates and use our pricing filter to set your maximum rate. You can also list your results by the most budget-friendly retreat first. > > > > - Search for the lowest price from CA $608 ### What's the difference between 5-star and 4-star hotels in Chester? > Offering a welcoming guest experience and upmarket décor, 4-star hotels are an excellent option for your Chester trip. These types of accommodations generally come with lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, gyms and restaurants. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in high-end perks and amenities. 24-hour front desk, complimentary toiletries and gourmet dining are typically featured at these swanky retreats. ### Does Chester have any 4-star all-inclusive resorts? > Finding your dream vacation in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. 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