Title: Chester Houseboats from CA $553 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/5fdecfa9ea611e8f8d02038dea5d1c0a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Search Houseboats in Chester from CA $553 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=HOUSE_BOAT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Houseboats ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1198x1y1-8dbb76d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-608c1c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-bea6e8a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-75aef492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cass-N-Reel Luxury Houseboat Grasonville 10/10 Exceptional (40) "We really enjoyed our stay. Looking forward to staying again!" [](https://www.expedia.ca/Grasonville-Hotels-Cass-N-Reel-Luxury-Houseboat.h94672644.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/9f651e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/30aed7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/57c49178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/5a48c8aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Floating 2 bed 2 bath condo stunning views of the bay Stevensville 6.8/10 (5) "Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. " [](https://www.expedia.ca/Stevensville-Hotels-Floating-2-Bed-2-Bath-Condo-Stunning-Views-Of-The-Bay.h105758639.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/955ec950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/0569c639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/949304ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/84be30a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Houseboat Getaway on Kent Island, Maryland Stevensville 9.8/10 Exceptional (42) "Just perfect for a 4 night stay." [](https://www.expedia.ca/Stevensville-Hotels-Chesapeake-Houseboat-Getaway-On-Kent-Island.h99712854.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/674bc712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/d131334a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/10010e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/9c7dbc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views Arnold 10/10 Exceptional (5) "Great visit! Outstanding experience, beautiful houseboat, great views!" CA $219 CA $553 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69340000/69337800/69337792/1e57e6b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69340000/69337800/69337792/482ea74f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69340000/69337800/69337792/86c6d1f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/70000000/69340000/69337800/69337792/9c1927ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cass-Away Luxury Houseboat Grasonville 10/10 Exceptional (103) "Unique and an interesting way to be close to the water." [](https://www.expedia.ca/Grasonville-Hotels-Cass-Away-Luxury-Houseboat.h69337792.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/90000000/89840000/89830200/89830151/w903h683x60y0-05b804cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89840000/89830200/89830151/w906h683x59y0-c203a8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/90000000/89840000/89830200/89830151/acfd1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89840000/89830200/89830151/w906h683x59y0-9e729bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo Houseboat Annapolis 10/10 Exceptional (2) "Comfortable with gorgeous views" [](https://www.expedia.ca/Annapolis-Hotels-Condo-Houseboat.h89830151.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/113000000/112110000/112100700/112100658/38dc4da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112110000/112100700/112100658/388778d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112110000/112100700/112100658/4e13737f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/113000000/112110000/112100700/112100658/32e4d77b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Nights on the Water - Classic Cruiser Getaway Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Downtown-Nights-On-The-Water-Classic-Cruiser-Getaway.h112100658.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99270000/99266100/99266070/422048f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99266100/99266070/3cb5a435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99270000/99266100/99266070/w1125h839x0y2-f4d295df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, bed sheets](https://images.trvl-media.com/lodging/100000000/99270000/99266100/99266070/2d686052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout. Edgewater CA $3,007 CA $4,247 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Edgewater-Hotels-Luxurious-50-Ft-Fountaine-Pajot-Saba-Six-Cabin-Six-Head-Layout.h99266070.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/d512df51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/852031b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/e9152c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/8774bb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views Pasadena CA $250 CA $631 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99260000/99253100/99253014/3c0aceef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99260000/99253100/99253014/e28c89ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, bed sheets](https://images.trvl-media.com/lodging/100000000/99260000/99253100/99253014/c901071b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99260000/99253100/99253014/w1125h839x0y2-38685b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Six bedroom 2020 Fountaine Pajot catamaran Edgewater [](https://www.expedia.ca/Edgewater-Hotels-Six-Bedroom-2020-Fountaine-Pajot-Catamaran.h99253014.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/121000000/120050000/120048500/120048412/567d1ee4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120050000/120048500/120048412/795948d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120050000/120048500/120048412/04f2fdab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120048500/120048412/94fe3c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom boat in amazing Annapolis with AC Historic District CA $1,503 CA $2,095 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Annapolis-Hotels-3-Bedroom-Boat-In-Amazing-Annapolis-With-AC.h120048412.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.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17®ionId=3000440455&adults=2&lodging=HOUSE_BOAT&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Houseboats.d3000440455-aaHouseboats.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Houseboats.d3000440455-aaHouseboats.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hyatt Place Kent Narrows & Marina](//images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Everything was fantastic." [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "The hotel was nice. The first room I got was still a mess because housekeeping didn’t clean that room. So I was given another room, which was clean as a whistle. Very good stay. I would definitely go back. Service was top tier." [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Great stop for what we had planned in the area" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "An easy walk to shops and restaurants. Position A." [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Great place." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Candlewood Suites Annapolis by IHG](//images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1_y.jpg) ### Candlewood Suites Annapolis by IHG 10/10 Excellent "Clean and comfortable room." [](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "This hotel was fantastic. I’m not sure what I was expecting, but it exceeded any expectations I may have had. I would definitely stay here again!" [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Clean room. Professional staff" [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ## Find out more about Chester ## Chester Houseboats information | Number of reviews | 192 | | --- | --- | | Accommodation | 11 Houseboats | | Lowest Price | CA $553 | | Highest Price | CA $4,247 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Kent Island](https://www.expedia.ca/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stevensville](https://www.expedia.ca/5Star-Stevensville-Hotels.s50-0-d162393.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976473602-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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