Title: 20 Best B&B in Chester, NY - Bed and Breakfast from $133 | 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 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 weeks [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 one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-29&endDate=2026-05-31&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) ![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) ### 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 8 - Apr 9 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) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.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) ### Borland House Inn [](https://www.expedia.com/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (157 reviews) "What a wonderful experience staying at the Borland House is! With the quaint, homey feeling of the whole house, to the kindness of the staff. Your stay will absolutely be lovely. Ample towels are provided for the private, spacious bathroom. Very comfortable bedding and well appointed decorations are in the bedroom. I was in the Hummingbird Suite. I could see myself living there, it just had everything I needed. I look forward to visiting again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $117 nightly $133 total Apr 7 - Apr 8 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) ![TV](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/cc3411cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/9e133beb.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) ### 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 $221 nightly $250 total Apr 14 - Apr 15 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) ![Hallway](https://images.trvl-media.com/lodging/105000000/104150000/104142500/104142495/d6fdabf0.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 $210 nightly $238 total Apr 13 - Apr 14 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) ![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) ![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) ### Alpine Haus Bed & Breakfast Inn [](https://www.expedia.com/Vernon-Hotels-Alpine-Haus-Bed-Breakfast-Inn.h1587870.Hotel-Information) Vernon 9.2/10 Wonderful (331 reviews) "Really nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $200 nightly $229 total Apr 6 - Apr 7 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) ![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) ![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) ![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) ### 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 Apr 15 - Apr 16 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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/ac02d781.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 9.6/10 Exceptional (97 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amrita $258 nightly $304 total Apr 6 - Apr 7 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) ![Interior entrance](https://images.trvl-media.com/lodging/17000000/16070000/16065100/16065013/7aba0c3a.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 Apr 8 - Apr 9 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=2026-04-19&endDate=2026-04-20®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 8/10 Good "Love the kitchen in the room. " [](https://expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "U" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 "Clean building and lovely staff. " [](https://expedia.com/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 10/10 Excellent "The upkeep on the property is fantastic. The staff are very courteous, helpful, and professional a great experience." [](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 10/10 Excellent "yes parking was good and breakfast was plentiful" [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great place. Clean room, good breakfast options, good facility. Highly recommend." [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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 "Friendly staff, free parking (!), quiet room & great breakfast with pancake machine." [](https://expedia.com/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.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 6/10 Okay "The design of the room made it impossible to watch TV and control it from bed. Very odd. " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Fantastic stay! Unique and castle-like property. Sandy was an amazing server at the high end restaurant. I recommend the tomahawk pork chop, which can be made into a gluten free dish. Cocktails were tasty and worth the calories. I would stay again! " [](https://expedia.com/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 1,235 | | ----------------- | ------ | | Accommodation | 12 B&B | | Lowest Price | $133 | | 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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