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 [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 two weeks [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 one month [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-22&endDate=2026-05-24&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/20000000/19450000/19441300/19441254/98e48046.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 Apr 6 - Apr 7 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) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.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) ![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) ### Borland House Inn [](https://www.expedia.com/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (157 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 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Borland-House-Inn.h11796055.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) ![Hallway](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/d6fdabf0.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) ![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) ### 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 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Columbus-Hotel.h104142495.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 (18 reviews) "Lovely property, owner and food! A gem!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Riley $231 nightly $262 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1590000/1587900/1587870/ecffd1a7.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 25 - Mar 26 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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2080000/2071800/2071739/4a024a6e.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 (393 reviews) "Special thanks to Billy the innkeeper! He was great and made our stay very enjoyable! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle $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) ![Interior entrance](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/6c09864d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/ac02d781.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) ### 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 $231 nightly $273 total Mar 25 - Mar 26 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) ![Lounge](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/36951f13.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) ### 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 25 - Mar 26 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=2026-04-07&endDate=2026-04-08®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 ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "Great Stay Would Definitely Stay Again" [](https://expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Did not use " [](https://expedia.com/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.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 4/10 Poor "I was highly disappointed. There was spitup on the bed rail and vents were extremely dirty. It's an older building too. There were cigarette stains on the dresser. No rooms were available to change and the housekeeper tired and clean but the presentation turned me off. " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.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 "Everything was great. Customer service was genuine and welcoming!! " [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 8/10 Good "Overall my experience was good. I was hoping for more scrambled eggs and bacon. There was a homeless guy living in his car that was a bit nerve racking, but otherwise harmless. " [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 8/10 Good "Parking was easy- lady at the front desk was great. Room was good " [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/f02832d4_y.jpg) ### Hampton Inn Nanuet 8/10 Good "." [](https://expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Hilton Garden Inn Nanuet](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca_y.jpg) ### Hilton Garden Inn Nanuet 8/10 Good "The front desk clerk was amazing when we checked in. The woman running the breakfast in the morning was pushy - pressuring us to buy the breakfast that we mistakenly thought was free. Overall, super convenient and clean. In the future, I'll be sure to pay a few extra bucks to add breakfast to our booking to avoid $15 for continental and $25 for a full breakfast (approx)." [](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 "Was very clean and nice " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 1,232 | | ----------------- | ------ | | 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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