Title: Best Cottages in Chester in 2026 | Expedia.co.uk [Chester Travel Guide](https://expedia.co.uk/Chester.dx89014)[Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d89014.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d89014.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d89014.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d89014.Holidays-City-Breaks) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [15 May - 17 May](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [12 Jun - 14 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=89014&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester cottages ![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro [](https://www.expedia.co.uk/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) Walpole 10/10 Exceptional (8 reviews) "Beautiful cozy cottage. Very clean. Wonderful host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria A. £200 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/171ffbfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish [](https://www.expedia.co.uk/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) Cavendish £437 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/e8e49a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/413e13e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/441c346c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/620f7707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK [](https://www.expedia.co.uk/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) Jamaica 10/10 Exceptional (3 reviews) "Nice and cozy, just like the listing shows. Great host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kytalia B. £194 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/7212c2d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/3655f9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/9b4bc035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/09450a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Mountain Home w/ Chefs Kitchen & Okemo Views [](https://www.expedia.co.uk/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information) Ludlow £1,570 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.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.co.uk/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09®ionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_89014) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=APARTMENT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=CABIN) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=COTTAGE) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=CHALET) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=VILLA) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d89014-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d89014-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Nice Pool Area" [](https://expedia.co.uk/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg) ### The Manchester View 10/10 Excellent "Clean, comfortable room." [](https://expedia.co.uk/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Great staff, clean rooms, great amenities and proximity of things to do and places to eat" [](https://expedia.co.uk/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/9c9da73f_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Our 2nd time staying here this season. We love it, perfect location to town and ski. Spotless rooms, microwave and fridge a bonus when kids are traveling. Rooms were so warm we turned off heat. Breakfast included. Check in and out very quick and friendly, we will absolutely stay again." [](https://expedia.co.uk/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg) ### Fullerton Inn 10/10 Excellent "Didn't catch the name of the gentleman at the front but he was so kind and accommodating, the space was very clean and a very quiet and cozy spot. Will definitely be going back!" [](https://expedia.co.uk/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Clean room and friendly staff " [](https://expedia.co.uk/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "The Pointe was much more than I expected (honestly). The room was large with a couch, reading chair (and ottoman) and small table and 2 chairs. The bathroom had a tub with jets. There was an indoor pool and hot tub-that worked. The one negative, no microwave in the room or common area— but the desk attendants, who were very very nice and accommodating, took care of that for me! And there was fresh brewed coffee in the lobby by 6 am!" [](https://expedia.co.uk/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Pool and sauna were wonderful after a day of skiing. Excellent breakfast. " [](https://expedia.co.uk/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg) ### Aspen At Manchester 10/10 Excellent "Solid updated motor lodge. Recommended" [](https://expedia.co.uk/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | | | ----------------- | -------- | | Accommodation | Cottages | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Why book your cottage in Chester with Expedia? ### How can I find cheap cottages in Chester? ### What is there to do in Chester near my cottage? ## Explore a world of travel with Expedia - More ways to book - [Book Cottages in Chester on Expedia.com ](https://www.expedia.com/Chester-Cottages.d89014-aaCottages.Travel-Guide-Accommodation)