Title: Chestertown Vacation Home Rentals from CA $175: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Chestertown Vacation Rentals ![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 Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/952fef86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/a1db5475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/bf6c1b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/688e056a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Bay Harbor View in a central location to events/restaurants Rock Hall CA $251 CA $300 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Rock-Hall-Hotels-Chesapeake-Bay-Harbor-View-In-A-Central-Location-To-Eventsrestaurants.h121084764.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax on Kent Island in 3 Bedroom Home w/Waterview Stevensville 9.8/10 Exceptional (41) "We had a great stay! The property has everything we needed and host was easy to communicate with " CA $116 CA $371 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/cfc4be94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/3addbd27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/7c4173a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/1055da7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern New Suite Close to US Capital and BWI Airport Pasadena 7.0/10 Good (2) "Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! " CA $105 CA $213 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Pasadena-Hotels-Modern-New-Townhouse-Close-To-US-Capital-And-BWI-Airport.h112909050.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/7a387636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Modern house with a full kitchen and parking Smyrna 9.8/10 Exceptional (8) "The house is a beautiful place to stay. The location was ideal for going to attractions and stores. " CA $251 CA $490 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/de679fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/b08b990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/e5dbb31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/6e19a811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable two-bedroom retreat close to Easton, Denton, Centreville Queen Anne 10/10 Exceptional (26) "Quiet, quaint....perfect" CA $215 CA $440 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Adorable-Two-Bedroom-Retreat-Close-To-Easton.h87799498.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/708da323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/97debd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e360a10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e33942cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay Glen Burnie 8.0/10 Very good (1) "The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the... CA $126 CA $175 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/ccc91804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/2ca0176e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/a32de752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/f853fb36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC Greektown 10/10 Exceptional (7) "This property was decorated beautifully. Roomy and functional. We enjoyed coffee on the rear deck. Neighborhood restaurants were great. We had great communication with our host. This trip far exceeded our expectations." CA $188 CA $314 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Baltimore-Hotels-Cozy-2-Bedroom-Apartment-In-Welcoming-Baltimore-With-WiFi.h116069925.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/2128b93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7d6d0051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7bb18c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/296e82bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Tide Haven Suite Kent County CA $242 CA $284 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/25541a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3c8498e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/9eb7ac3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HGTV quality, private guest suite, country getaway with hot tub & fire pit Centreville 10/10 Exceptional (6) "Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!" CA $305 CA $658 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/89a58d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/4ee38359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/da0262a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️ Stevensville 9.6/10 Exceptional (30) "Nice and peaceful stay for a quick local getaway. " CA $116 CA $367 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/9fcdfcad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/61b9de4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/a815bd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/b3eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Tiny Pool House -Private Pool -Self Check in Glen Burnie 8.8/10 Excellent (9) "Absolutely loved it, very quiet and peaceful, Jordan is an excellent host" CA $166 CA $221 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/CLEAN.h109465066.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116240000/116236700/116236613/b4035dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/117000000/116240000/116236700/116236613/c08d4f3a_edited_6e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116240000/116236700/116236613/4b78eb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116240000/116236700/116236613/0c8fec18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC Aberdeen CA $128 CA $330 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Aberdeen-Hotels-Charming-1-Bedroom-Basement-In-Enjoyable-Aberdeen-With-WiFi.h116236613.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/166bb313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/882747f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Cottage steps from Rock Hall Harbor Rock Hall 10/10 Exceptional (2) "Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!" CA $244 CA $492 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. Grasonville 9.6/10 Exceptional (12) "Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. " CA $349 CA $575 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/cc3df3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/f9a89b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Pet-Friendly Stay - Near Bay & Beaches. Annapolis 10/10 Exceptional (5) "The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here." CA $393 CA $869 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/b71a43f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/d42b5ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/3751c07c_edited_5953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/1837dc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker Berea 9.6/10 Exceptional (4) "Everything was great, easy check in and simple and clean space!!! Amazing thank you" CA $251 CA $436 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Baltimore-Hotels-Family-Friendly-2-Bedroom-House-In-Welcoming-Baltimore-With-WiFi.h108444163.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-5f725067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-97b0328a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h508x0y136-4ba3382c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h574x0y103-120745ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hideaway Spot- Waterfront w/ Dock on Long Cove Glen Burnie 8.4/10 Very good (7) "The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect." CA $152 CA $486 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115840000/115836600/115836595/9afad3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/116000000/115840000/115836600/115836595/2270818e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115840000/115836600/115836595/10b28666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115840000/115836600/115836595/ed9d7a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern and Cozy Home in Bel Air with a Home Office and Fireplace Bel Air 10/10 Exceptional (3) "The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. " CA $294 CA $423 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bel-Air-Hotels-Modern-And-Cozy-Home-In-Bel-Air-With-A-Home-Office-And-Fireplace.h115836595.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111070000/111068900/111068893/4cac5d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111070000/111068900/111068893/ef2d1c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111070000/111068900/111068893/654a444a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111070000/111068900/111068893/54d1a739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions. Glen Burnie 10/10 Exceptional (3) "This home had everything we needed and more. I say home because it felt like home when we walked in. Super cozy and comfortable. The basement was perfect for our family playing card games. Kitchen had everything we needed. We'll definitely see if this place is avaliable on our next visit. " CA $314 CA $404 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Glen-Burnie-Hotels-Glen-Burnie-Hideaway-Pet-Friendly-With-Easy-Access-To-Multiple-Attractions.h111068893.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/7fa2b473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/76c1b6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Fells Point Gem / Private Courtyard Patio Fells Point 9.6/10 Exceptional (88) "Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!" CA $86 CA $285 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.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=2025-10-22&endDate=2025-10-23®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FChestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent stay but I never received my wine " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!" [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](//images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 10/10 Excellent "Clean building, Beds are comfortable, Breakfasts was good" [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](//images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "Very nice staff" [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Easy access, dmooth check in, felt safe parking, close to port. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](//images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Clean and spacious room with great amenities " [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![SpringHill Suites Baltimore White Marsh/Middle River](//images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_y.jpg) ### SpringHill Suites Baltimore White Marsh/Middle River 10/10 Excellent "Great place to stay, better than any of the other hotels in the middle river area." [](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](//images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 10/10 Excellent "Didn’t have made to order breakfast. They’re many shops nearby. Room was clean and fresh. " [](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![The Inn at Henderson's Wharf, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel 10/10 Excellent "Excellent location Lots of shops and restaurants Quiet" [](https://expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ## Find out more about Chestertown ## Chestertown Vacation Homes information | Number of reviews | 212 | | --- | --- | | Accommodation | 518 Vacation Homes | | Lowest Price | CA $175 | | Highest Price | CA $869 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Best Western Hotels in Aberdeen Proving Ground](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels-Best-Western.0-0-d553248634999428212--bBestWestern.Travel-Guide-Filter-Hotels) - 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