Title: 20 Best B&B in Chester, NY - Bed and Breakfast from $119 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6046665)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6046665.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d6046665.Destination-Travel-Guides) ![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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/117bcdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Primrose) | Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/0c3a1284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/f9a6b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/3cff05ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast [](https://www.expedia.com/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) Chester 9.2/10 Wonderful (233 reviews) "Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erek $215 nightly $243 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/2154c327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/20894557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.com/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (155 reviews) "Our room was beautiful and well maintained and spotlessly clean. I did not realize before we came to the hotel that the bathroom was out in the hall, not en suite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea $105 nightly $119 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/a9ea5c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/30c7644a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/9e133beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/cc3411cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Verde BB Greenwood Lake NY [](https://www.expedia.com/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) Monroe 10/10 Exceptional (17 reviews) "Lovely property, owner and food! A gem!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Riley $211 nightly $239 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) ![Individually decorated, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/c887d5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/3c2fa034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/8eaa85b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/d6fdabf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Columbus Hotel [](https://www.expedia.com/Middletown-Hotels-Columbus-Hotel.h104142495.Hotel-Information) Middletown 6.0/10 (6 reviews) "21 minutes ago on Google It's a family owned and operated hotel. Norman was kind, communicative and thorough. Keyless entry made checking in super easy. We had a business suite, which is basically a studio apartment. Kitchen , bathroom, bed/living space was clean and neat having a really nice modern clean aesthetic. There was even a candle left for us to enjoy. Overall was a very pleasant stay! Very grateful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane $209 nightly $237 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Columbus-Hotel.h104142495.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/0db4b471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/598f2dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/ecffd1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Quadruple Room, Ensuite (Violet Suite #10)](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/cb3af20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alpine Haus Bed & Breakfast Inn [](https://www.expedia.com/Vernon-Hotels-Alpine-Haus-Bed-Breakfast-Inn.h1587870.Hotel-Information) Vernon 9.2/10 Wonderful (330 reviews) "Really nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $200 nightly $229 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Alpine-Haus-Bed-Breakfast-Inn.h1587870.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/5582c6a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/88bfde2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/4a024a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/29ea3928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Castle at Skylands Manor [](https://www.expedia.com/Ringwood-Hotels-The-Castle-At-Skylands-Manor.h2071739.Hotel-Information) Ringwood 7.4/10 Good (392 reviews) "If you want a quiet, historical experience, then this is the venue. It's not new, shiny - but that is not why you go there. It is a beautiful Tudor-style hotel, with old fixtures, antique windows, and the charm of a storybook castle. The innkeeper is lovely and the grounds are beautiful. We missed peak colors by a week or two and are considering a quick trip back! Buffet breakfast was just right." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lesli $175 nightly $195 total Mar 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Ringwood-Hotels-The-Castle-At-Skylands-Manor.h2071739.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/383d1993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/126b99ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/a124fb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/6c09864d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cromwell Manor Inn [](https://www.expedia.com/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) Cornwall 9.4/10 Exceptional (95 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amrita $281 nightly $332 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/952dd0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/7aba0c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/36951f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/1b99f6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stagecoach Inn [](https://www.expedia.com/Newburgh-Hotels-Stagecoach-Inn.h16065013.Hotel-Information) Goshen 9.6/10 Exceptional (79 reviews) "We only stayed one night, but it was very comfortable and the staff was friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn $282 nightly $347 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Stagecoach-Inn.h16065013.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.com/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03®ionId=6046665&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Bed-And-Breakfast.d6046665-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Bed-And-Breakfast.d6046665-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e_y.jpg) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 10/10 Excellent "Clean rooms,comfy bed, great continental breakfast." [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Great stay! Clean, friendly and accommodating! " [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 8/10 Good "Clean room, safe and staff is courteous " [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/f02832d4_y.jpg) ### Hampton Inn Nanuet 8/10 Good "These rooms are in decent shape and we've been coming to this hotels for more than 15 years now. The cleanings have changed and are now every other day. The issues we encountered was the bathroom tub draining very slowly and the refrigerator freezing our drinks. Otherwise a quiet, restful stay." [](https://expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/d3089562_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "Clean meet my requirements " [](https://expedia.com/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg) ### Hampton Inn & Suites Newburgh Stewart Airport 10/10 Excellent "Everything was perfect " [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Courtyard by Marriott Fishkill](https://images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg) ### Courtyard by Marriott Fishkill 10/10 Excellent "Staff was very nice . Gave us water bottles , and i loved that they didn’t come knocking on the door as soon as it was checkout time" [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/ae4d02f3_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "One of the most comfortable beds we’ve slept on. Lovely staff, good breakfast and lovely holiday decor when we’d stayed. " [](https://expedia.com/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9_y.jpg) ### Sonesta Simply Suites Nanuet 4/10 Poor "." [](https://expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 836 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $119 | | Highest Price | $347 | ## Frequently asked questions ### What are the most popular Chester Bed & Breakfasts? ### What is the nightly rate for a B&B in Chester? ### When is the best time to book a Bed and Breakfast in Chester? > July stands out as the peak month, attracting visitors eager to engage in water sports, hiking, and exploring the picturesque landscape. Temperatures typically range from the mid-70s to low 90s Fahrenheit, providing superb conditions for outdoor adventures. Whether you're picnicking by the lake or taking a scenic hike in the Lassen National Forest, you'll find plenty of opportunities for relaxation and recreation. > > > For those looking for a more budget-friendly option, October is a wonderful time to visit Chester. With the summer crowds dissipating, you can enjoy the stunning fall foliage that blankets the region in vibrant colors, all while experiencing a more tranquil atmosphere. This is also a great time for cozy fireside evenings at your B&B, adding a touch of warmth to your stay. ### What is the difference between a Chester B&B and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Castle Fun Center ](https://www.expedia.com/Castle-Fun-Center-Hotels.0-l6209270-0.Travel-Guide-Filter-Hotels) - [Hotels near Museum Village ](https://www.expedia.com/Museum-Village-Hotels.0-l553248621559142200-0.Travel-Guide-Filter-Hotels) - [Hotels near LEGOLAND® New York ](https://www.expedia.com/LEGOLAND-New-York-Hotels.0-l553248635997928006-0.Travel-Guide-Filter-Hotels) - [Hotels near The Rock Sports Complex ](https://www.expedia.com/The-Rock-Sports-Complex-Hotels.0-l553248624556330411-0.Travel-Guide-Filter-Hotels) - [Hotels near Goosepond Mountain State Park ](https://www.expedia.com/Goosepond-Mountain-State-Park-Hotels.0-l553248635974861777-0.Travel-Guide-Filter-Hotels) - 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