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 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-08&endDate=2026-05-10&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) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/3cff05ce.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) ### 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 16 - Mar 17 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 sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.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) ![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 (154 reviews) "Breakfast was hot and tasty. Staff were all pleasant and accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) wendy $105 nightly $119 total Mar 15 - Mar 16 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) ![Restaurant](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/9e133beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/78872596.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) "Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary $174 nightly $197 total Mar 23 - Mar 24 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) ![Exterior](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/8eaa85b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, oven, stovetop, coffee grinder](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/0408748d.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) ### 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) ![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) ![Luxury Quadruple Room, Ensuite (Violet Suite #10)](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/751f1365.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) "We had a great weekend stay at Alpine! The caretaker, Anil was so hospitable! We will definitely be back soon!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krystal $200 nightly $229 total Mar 12 - Mar 13 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) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/4a024a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom, Garden View (Queen Antoinette Suite) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/1ff0efd3.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) ### 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 18 - Mar 19 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) ![Reception](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/a124fb3e.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) ![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 $296 nightly $349 total Mar 12 - Mar 13 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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/c90ab9b7.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) ### 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 12 - Mar 13 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=2026-03-25&endDate=2026-03-26®ionId=6046665&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6046665) ![](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 ![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 very welcoming staff " [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg) ### Courtyard by Marriott Newburgh Stewart Airport 2/10 Terrible "The lady that checked us in was rude Jacuzzi closed restaurant closed bar closed very disappointing" [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.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 8/10 Good "Good " [](https://expedia.com/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Hilton Garden Inn Nanuet](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca_y.jpg) ### Hilton Garden Inn Nanuet 10/10 Excellent "The staff at the reception desk always kind, professionals and helpful. The room very clean and you don't hear any unwanted noises. " [](https://expedia.com/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Great stay!!! " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9_y.jpg) ### Sonesta Simply Suites Nanuet 2/10 Terrible "The cleanness of the hotel is disgusting. I would never recommend anyone to that hotel. It’s the worst and I mean the worst stuff no good the rooms no good even the toilet flood over so the cleanness and the staff is no good. I was so disappointed and disgusted of that Hotel. " [](https://expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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 "Very friendly staff. Quick and easy check in. Clean room. " [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![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 "nice having an indoor pool...area is very slippery when kids are splashing outside of pool...hot tub and having shower there great" [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 6/10 Okay "Could not connect to internet in room. Only in lobby. " [](https://expedia.com/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 835 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $119 | | Highest Price | $349 | ## 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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