Title: Massey Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Massey](https://expedia.ca/Massey-Hotels.d3000440702.Travel-Guide-Hotels)[Vacation Rentals in Massey](https://expedia.ca/Massey-Vacation-Rentals.d3000440702.Travel-Guide-VacationRentals)[Massey Car Rentals](https://expedia.ca/Car-Rentals-In-Massey.d3000440702.Car-Rental-Guide)[Massey Vacation Packages](https://expedia.ca/Massey.d3000440702.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Massey 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 In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000440702&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Massey Vacation Homes ![Outdoor spa tub](https://images.trvl-media.com/lodging/69000000/68060000/68050800/68050736/c8581853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68060000/68050800/68050736/e76935e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68060000/68050800/68050736/a12bc9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68060000/68050800/68050736/20474c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sailor's Sunrise Cottage - Chesapeake Bay Perryville 9.4/10 Exceptional (53) "It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! " [](https://www.expedia.ca/Perryville-Hotels-Sailors-Sunrise-Cottage-Chesapeake-Bay.h68050736.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/e3526265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/6f840824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/4e7c5213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/c370010d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Circa 1900 Home in the Heart of Historic Downtown Chestertown Chestertown 10/10 Exceptional (74) "Great house, will stay again in the future. " [](https://www.expedia.ca/Chestertown-Hotels-Circa-1900-Home-In-The-Heart-Of-Historic-Downtown-Chestertown.h66473084.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117420000/117414100/117414082/3aedc0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117420000/117414100/117414082/8b2b4e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/118000000/117420000/117414100/117414082/2eaff22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117420000/117414100/117414082/67ce6090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun! Chesapeake City 10/10 Exceptional (1) "The property is exactly as you see in the pictures/description. We were 4 adults, 4 kids (9 months to 13 years). Plenty of room for all of us. Hosts were quick to respond to any messages sent.Had a great 3 days here." [](https://www.expedia.ca/Chesapeake-City-Hotels-Charming-Queen-Of-Chesapeake-City.h117414082.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/ae7d8ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/1085cffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/5457dac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/265dbeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lark's Nest on the Chester River. Spacious, waterfront home with private dock. Millington 9.6/10 Exceptional (22) "Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! " [](https://www.expedia.ca/Millington-Hotels-Larks-Nest-On-The-Chester-River-Spacious.h99280632.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/79000000/78370000/78364200/78364159/d2fafc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78370000/78364200/78364159/6de42630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78370000/78364200/78364159/c0385e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78370000/78364200/78364159/476b906d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Point | Waterfront w/ HOT TUB + Beach! Elkton 9.8/10 Exceptional (18) "Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group." [](https://www.expedia.ca/Elkton-Hotels-Waterfront-Home-W-A-Hot-Tub.h78364159.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99540000/99538900/99538899/77aa21e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99540000/99538900/99538899/43d2bae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99540000/99538900/99538899/d2b358f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99540000/99538900/99538899/bf6ea751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake City Quiet Overlook Chesapeake City 10/10 Exceptional (21) "We had a wonderful stay in Chesapeake City! The property was very clean, well stocked, and perfect for our family. The kitchen is gorgeous with a beautiful view of the water, and everything is labeled so items are easy to find and put away. Just a short walk to dinner at Schaefer’s Canal House and the trail. Highly recommend!" [](https://www.expedia.ca/Chesapeake-City-Hotels-Chesapeake-City-Quiet-Overlook.h99538899.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118140000/118131400/118131345/f51e7c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118140000/118131400/118131345/13c30a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118140000/118131400/118131345/c1784451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/119000000/118140000/118131400/118131345/75c0d265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Lodge packed with Amenities Earleville 10/10 Exceptional (2) "Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. " [](https://www.expedia.ca/Earleville-Hotels-Waterfront-Lodge-Packed-With-Amenities.h118131345.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108970000/108966100/108966012/86cdd46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/109000000/108970000/108966100/108966012/6e7d5bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/109000000/108970000/108966100/108966012/6bc2a20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108970000/108966100/108966012/04cda9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland. Kennedyville 8.6/10 Excellent (4) "Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests." [](https://www.expedia.ca/Kennedyville-Hotels-Spacious-4-Bedroom-House-With-AC-And-WiFi-In-Charming-Kennedyville.h108966012.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107180000/107177200/107177146/7a2c90c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107180000/107177200/107177146/cf0f0da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107180000/107177200/107177146/73effd9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107180000/107177200/107177146/b4d92ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious and spacious townhome with all necessary amenities awaits your stay. Middletown 9.4/10 Exceptional (9) "Great experience all around! " [](https://www.expedia.ca/Middletown-Hotels-Luxurious-And-Spacious-Townhome-With-All-Necessary-Amenities-Awaits-Your-Stay.h107177146.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/a6438229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/cee3d56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/26e808a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/c4667d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!! Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Stunning-Historic-Downtown-Home-Within-2-Blocks-Of-Fountain-Park.h119124197.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36710000/36702800/36702768/d9352f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36710000/36702800/36702768/313518ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36710000/36702800/36702768/8b02e6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36710000/36702800/36702768/684f1c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal Chesapeake City 10/10 Exceptional (70) "Nice home great lication" [](https://www.expedia.ca/Chesapeake-City-Hotels-Spring-Season-In-Chesapeake-City.h36702768.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106300000/106293800/106293774/7337b625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106300000/106293800/106293774/29af44ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106300000/106293800/106293774/e467ff9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106300000/106293800/106293774/4ff6ff1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Countryside Cottage in Sassafras Galena [](https://www.expedia.ca/Galena-Hotels-Cozy-4-Bedroom-House-On-Quiet-Farm.h106293774.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/82000000/81600000/81596000/81595927/636b02c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81600000/81596000/81595927/9f08302c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81600000/81596000/81595927/9cdcb643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/82000000/81600000/81596000/81595927/w1242h1656x0y276-b7b175ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. Galena 9.8/10 Exceptional (21) "Beautiful property overlooking the Sassafras river. Home and property above and beyond pictures. Renter easy to work with and accommodating " [](https://www.expedia.ca/Galena-Hotels-Riverfront-Country-House-On-The-Sassafras-River.h81595927.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95450000/95442700/95442685/5453817a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, computer monitors](https://images.trvl-media.com/lodging/96000000/95450000/95442700/95442685/45f4f04c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95450000/95442700/95442685/c4b33209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95450000/95442700/95442685/b3e330b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown Chestertown 10/10 Exceptional (5) "We rented for my daughter’s graduation from Washington college. Wonderful home that was decorated great with a perfect location!!! " [](https://www.expedia.ca/Chestertown-Hotels-The-Portside-Manor-Queen-Street-Chestertown-Walking-Distance-To-Downtown.h95442685.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103500000/103491300/103491295/e5f2fff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103500000/103491300/103491295/fe90f0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103500000/103491300/103491295/47e3a423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103500000/103491300/103491295/58605fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your perfect Maryland escape awaits! Galena 10/10 Exceptional (4) "Our group had another great stay. The house is exactly as pictured and the host is very responsive. Everything was perfect from checkin to departure. We will definitely stay at this house again!! " [](https://www.expedia.ca/Galena-Hotels-Your-Perfect-Maryland-Escape-Awaits.h103491295.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484099/73e9cabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484099/87f3f652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484099/55fe4bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484099/ec5e6827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Bay House with Dock & Private Beach Elkton 10/10 Exceptional (172) "Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip." [](https://www.expedia.ca/Elkton-Hotels-Chesapeake-Bay-House-With-Dock-Private-Beach.h33484099.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/84000000/83920000/83911600/83911536/ee9ab64f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83920000/83911600/83911536/0dc70f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/84000000/83920000/83911600/83911536/2e8e9339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/84000000/83920000/83911600/83911536/9552f8af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captivating Chesapeake experience Perryville 10/10 Exceptional (276) "We had such a great weekend at this property. It was beautiful and such a relaxing location. House had everything we needed. We hope to be back!! " [](https://www.expedia.ca/Perryville-Hotels-Captivating-Chesapeake-Experience.h83911536.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36630000/36620300/36620295/440a6c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/37000000/36630000/36620300/36620295/130c9da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/37000000/36630000/36620300/36620295/e0e867f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36630000/36620300/36620295/w1439h1075x0y0-a28a7cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nancy’s Touch, A Waterfront Paradise! North East 10/10 Exceptional (169) "Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. " [](https://www.expedia.ca/North-East-Hotels-Nancys-Touch.h36620295.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/75000000/74900000/74897600/74897548/d4423928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74900000/74897600/74897548/6963802b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/75000000/74900000/74897600/74897548/50440bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74900000/74897600/74897548/777db167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach Betterton 9.6/10 Exceptional (44) "This is a jewel as it is private, peaceful with lovely setting." [](https://www.expedia.ca/Betterton-Hotels-Historic-Waterfront-Home-With-Chesapeake-Bay-View-Sleeps-9-Close-To-The-Beach.h74897548.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/72000000/71100000/71092300/71092207/bd800064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71100000/71092300/71092207/bea49d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71100000/71092300/71092207/78376f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71100000/71092300/71092207/8ff0a148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!! Chesapeake City 9.8/10 Exceptional (6) "We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. " [](https://www.expedia.ca/Chesapeake-City-Hotels-Hook-Wine-Sinkersleeps-14-To-16-Includes-Slip-At-Inn-Water-Views.h71092207.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=2025-10-11&endDate=2025-10-12®ionId=3000440702&adults=2&lodging=VACATION_HOME&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%2FMassey-Private-Vacation-Homes.d3000440702-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMassey-Private-Vacation-Homes.d3000440702-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Massey Hotel Reviews ![Holiday Inn Express Hotel & Suites Dover by IHG](//images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg) ### Holiday Inn Express Hotel & Suites Dover by IHG 10/10 Excellent "We stay here every year and love it. Rooms are really spacious and clean. " [](https://expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "This is our 4th, 5th or 6th stay here (lost count) and always find the staff very friendly and courteous. The rooms are always clean, beds are so comfortable (Thank You!), air conditioner works, and the breakfast is wonderful! It's like a full on breakfast and the lady that's in charge of it keeps everything stocked and counters wiped down. Excellent experience that every hotel should use as a model. " [](https://expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information) ![Bally's Dover Casino Resort](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "The facility was very clean & comfortable. The only thing that would have been better, if the hotel check in area was better marked (as their check in area), and if the desk for that was closer to the entrance door. It was a walk across a very large area, inside the building, which was hard if you use a walker or cane." [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Hilton Garden Inn Dover](//images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/eab21539_y.jpg) ### Hilton Garden Inn Dover 10/10 Excellent "Staff was amazing. Room was very clean" [](https://expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Great property" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Fairfield Inn & Suites by Marriott Middletown](//images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 10/10 Excellent "All the staff was so attentive and kind. It’s located next to a several strips malls one of which is walking distance. The breakfast is substantial and there’s a pretty patio to use in nice weather. " [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Sleep Inn And Suites](//images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/558d764a_y.jpg) ### Sleep Inn And Suites 10/10 Excellent "Everything is perfect " [](https://expedia.ca/Dover-Hotels-Sleep-Inn-And-Suites.h2115064.Hotel-Information) ![Holiday Inn Express & Suites Middletown by IHG](//images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131_y.jpg) ### Holiday Inn Express & Suites Middletown by IHG 10/10 Excellent "safe quiet easyparking" [](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Comfort Suites Dover](//images.trvl-media.com/lodging/1000000/50000/42300/42248/7377e77e_y.jpg) ### Comfort Suites Dover 10/10 Excellent "Could not flush toilet first night and the sink stopper would not open. I had to use my finger to make it rise. The carpet and curtains were stained. The breakfast was extremely poor with no bread available and milk was in a cup. How ever the bed and pillows were excellent. " [](https://expedia.ca/Dover-Hotels-Comfort-Suites-Dover.h42248.Hotel-Information) ## Find out more about Massey ## Massey Vacation Homes information | Number of reviews | 940 | | --- | --- | | Accommodation | 70 Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Chesapeake City](https://www.expedia.ca/4Star-Chesapeake-City-Hotels.s40-0-d177517.Travel-Guide-Filter-Hotels) - [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) - [Aberdeen Proving Ground Hotels](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels.d553248634999428212.Travel-Guide-Hotels) - [Apartments in Betterton](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Cottages in Betterton](https://www.expedia.ca/Betterton-Cottages.d3000440429-aaCottages.Travel-Guide-Accommodation) - [Betterton Hotels](https://www.expedia.ca/Betterton-Hotels.d3000440429.Travel-Guide-Hotels) - [Resorts in Betterton](https://www.expedia.ca/Betterton-Resort-Hotels.d3000440429-aaResortHotels.Travel-Guide-Accommodation) - [Cecilton Hotels](https://www.expedia.ca/Cecilton-Hotels.d177525.Travel-Guide-Hotels) - [Cheap Hotels in Charlestown](https://www.expedia.ca/Charlestown-Hotels-Cheap-Hotels.0-0-d553248634999088358-tCheapHotels.Travel-Guide-Filter-Hotels) - [Charlestown Hotels](https://www.expedia.ca/Charlestown-Hotels.d553248634999088358.Travel-Guide-Hotels) - [Cheap Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Cheap-Hotels.0-0-d177517-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Golf-Hotel.0-0-d177517-tGolfHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Luxury-Hotel.0-0-d177517-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Marriott-Hotels-Resorts.0-0-d177517--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Spa Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Spa-Hotel.0-0-d177517-tSpaHotel.Travel-Guide-Filter-Hotels) - [Chesapeake City Hotels](https://www.expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels) - [Inns in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Inns.d177517-aaInns.Travel-Guide-Accommodation) - [Farmstay in Chestertown](https://www.expedia.ca/Chestertown-Agritourism.d7215-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Chestertown](https://www.expedia.ca/Chestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Beach-Hotel.0-0-d7215-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Cheap-Hotels.0-0-d7215-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Hotels-With-Free-Breakfast.0-0-d7215-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Luxury-Hotel.0-0-d7215-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Oceanfront-Hotels.0-0-d7215-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Pet-Friendly-Hotel.0-0-d7215-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Chestertown Hotels](https://www.expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels) - [Inns in Chestertown](https://www.expedia.ca/Chestertown-Inns.d7215-aaInns.Travel-Guide-Accommodation) - [Resorts in Chestertown](https://www.expedia.ca/Chestertown-Resort-Hotels.d7215-aaResortHotels.Travel-Guide-Accommodation) - [Riads in Chestertown](https://www.expedia.ca/Chestertown-Riads.d7215-aaRiads.Travel-Guide-Accommodation) - [Cheap Hotels in Church Hill](https://www.expedia.ca/Church-Hill-Hotels-Cheap-Hotels.0-0-d6359186-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Church Hill](https://www.expedia.ca/Church-Hill-Hotels-Hotels-With-Hot-Tubs.0-0-d6359186-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Church Hill Hotels](https://www.expedia.ca/Church-Hill-Hotels.d6359186.Travel-Guide-Hotels) - [Inns in Church Hill](https://www.expedia.ca/Church-Hill-Inns.d6359186-aaInns.Travel-Guide-Accommodation) - [Cecil County Hotels](https://www.expedia.ca/Destinations-In-Cecil-County.d553248635976434204.Hotel-Destinations) - [Earleville Hotels](https://www.expedia.ca/Earleville-Hotels.d6359189.Travel-Guide-Hotels) - [Hotels near Elk Neck State Park](https://www.expedia.ca/Elk-Neck-State-Park-Hotels.0-l553248621532662916-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Business-Hotel.0-0-d7834-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Cheap-Hotels.0-0-d7834-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Pet-Friendly-Hotel.0-0-d7834-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Spa-Hotel.0-0-d7834-tSpaHotel.Travel-Guide-Filter-Hotels) - [Elkton Hotels](https://www.expedia.ca/Elkton-Hotels.d7834.Travel-Guide-Hotels) - [B&B in Galena](https://www.expedia.ca/Galena-Bed-And-Breakfast.d106992-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels with Hot Tubs in Galena](https://www.expedia.ca/Galena-Hotels-Hotels-With-Hot-Tubs.0-0-d106992-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Galena](https://www.expedia.ca/Galena-Hotels-Romantic-Hotel.0-0-d106992-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Galena Hotels](https://www.expedia.ca/Galena-Hotels.d106992.Travel-Guide-Hotels) - [Lodges in Galena](https://www.expedia.ca/Galena-Lodges.d106992-aaLodges.Travel-Guide-Accommodation) - [Motels in Galena](https://www.expedia.ca/Galena-Motels.d106992-aaMotels.Travel-Guide-Accommodation) - [Resorts in Galena](https://www.expedia.ca/Galena-Resort-Hotels.d106992-aaResortHotels.Travel-Guide-Accommodation) - [Independent Hotels in Georgetown](https://www.expedia.ca/Georgetown-Hotels-Independent.0-0-d553248635975874069--bIndependent.Travel-Guide-Filter-Hotels) - [Great Oak Landing Hotels](https://www.expedia.ca/Great-Oak-Landing-Hotels.d3000045661.Travel-Guide-Hotels) - [Henderson Hotels](https://www.expedia.ca/Henderson-Hotels.d3000440669.Travel-Guide-Hotels) - [Hotels near Historical Society of Cecil County](https://www.expedia.ca/Historical-Society-Of-Cecil-County-Hotels.0-l553248621561879715-0.Travel-Guide-Filter-Hotels) - [Lodges in Kennedyville](https://www.expedia.ca/Kennedyville-Lodges.d3000440679-aaLodges.Travel-Guide-Accommodation) - [Farmstay in Marydel](https://www.expedia.ca/Marydel-Agritourism.d3000430745-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Marydel](https://www.expedia.ca/Marydel-Apart-Hotels.d3000430745-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Marydel](https://www.expedia.ca/Marydel-Bed-And-Breakfast.d3000430745-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Marydel Hotels](https://www.expedia.ca/Marydel-Hotels.d3000430745.Travel-Guide-Hotels) - [Millington Hotels](https://www.expedia.ca/Millington-Hotels.d3000440734.Travel-Guide-Hotels) - [North East Hotels](https://www.expedia.ca/North-East-Hotels.d139151.Travel-Guide-Hotels) - [Pomona Hotels](https://www.expedia.ca/Pomona-Hotels.d553248635976007038.Travel-Guide-Hotels) - [Red Point Hotels](https://www.expedia.ca/Red-Point-Hotels.d553248635975869447.Travel-Guide-Hotels) - [Still Pond Hotels](https://www.expedia.ca/Still-Pond-Hotels.d3000347996.Travel-Guide-Hotels) - [Lodges in Still Pond](https://www.expedia.ca/Still-Pond-Lodges.d3000347996-aaLodges.Travel-Guide-Accommodation) - [Villas in Still Pond](https://www.expedia.ca/Still-Pond-Villas.d3000347996-aaVillas.Travel-Guide-Accommodation) - [Cottages in Templeville](https://www.expedia.ca/Templeville-Cottages.d553248634998688186-aaCottages.Travel-Guide-Accommodation) - [B&B in Warwick](https://www.expedia.ca/Warwick-Bed-And-Breakfast.d553248635975870671-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Warwick](https://www.expedia.ca/Warwick-Guest-Houses.d553248635975870671-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Warwick](https://www.expedia.ca/Warwick-Hotels-Cheap-Hotels.0-0-d553248635975870671-tCheapHotels.Travel-Guide-Filter-Hotels) - [Warwick Hotels](https://www.expedia.ca/Warwick-Hotels.d553248635975870671.Travel-Guide-Hotels) - [Motels in Warwick](https://www.expedia.ca/Warwick-Motels.d553248635975870671-aaMotels.Travel-Guide-Accommodation) - [Resorts in Warwick](https://www.expedia.ca/Warwick-Resort-Hotels.d553248635975870671-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Washington College](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Aparthotels in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Apart-Hotels.d553248635975865930-aaApartHotels.Travel-Guide-Accommodation) - [B&B in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Bed-And-Breakfast.d553248635975865930-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Cottages.d553248635975865930-aaCottages.Travel-Guide-Accommodation) - [White Crystal Beach Hotels](https://www.expedia.ca/White-Crystal-Beach-Hotels.d553248635975865930.Travel-Guide-Hotels) - [Motels in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Motels.d553248635975865930-aaMotels.Travel-Guide-Accommodation) - [Resorts in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Resort-Hotels.d553248635975865930-aaResortHotels.Travel-Guide-Accommodation) - [Worton Hotels](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels) - [Flights to Chestertown](https://www.expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights) - [Flights to Elkton](https://www.expedia.ca/Cheap-Flights-To-Elkton.d7834.Travel-Guide-Flights) - [Flights to North East](https://www.expedia.ca/Cheap-Flights-To-North-East.d139151.Travel-Guide-Flights) - [Flights from Kennedyville](https://www.expedia.ca/lp/flights/3000440679/flights-from-kennedyville) - [Flights from Barclay](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay) - [Flights from Aberdeen Proving Ground](https://www.expedia.ca/lp/flights/553248634999428212/flights-from-aberdeen-proving-ground) - [Flights from Chestertown](https://www.expedia.ca/lp/flights/7215/flights-from-chestertown) - [Flights from Elkton](https://www.expedia.ca/lp/flights/7834/flights-from-elkton) - [Visit Chesapeake City](https://www.expedia.ca/Chesapeake-City.dx177517) - [Visit Elkton](https://www.expedia.ca/Elkton.dx7834) - [Historical Society of Kent County Maryland](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Mount Harmon Plantation](https://www.expedia.ca/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction) - [North East Vacations](https://www.expedia.ca/North-East.d139151.Destination-Travel-Guides) - [Wilmer Park](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Budget Rental Cars in Chestertown](https://www.expedia.ca/Budget-Car-Rentals-In-Chestertown.d7215-c39.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Elkton](https://www.expedia.ca/Budget-Car-Rentals-In-Elkton.d7834-c39.Car-Rental-Guide-Suppliers) - [Car rentals in Budget Santa Maria Public Airport - 3249 Terminal Dr](https://www.expedia.ca/Budget-at-Santa-Maria-Public-Airport-3249-Terminal-Dr-Santa-Maria-California-USA.v7834.Car-Rental-Guide-Location) - [Car rental Chestertown](https://www.expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) - [Car rental Elkton](https://www.expedia.ca/Car-Rentals-In-Elkton.d7834.Car-Rental-Guide) - [Enterprise Rental Cars in Aberdeen Proving Ground](https://www.expedia.ca/Enterprise-Car-Rentals-In-Aberdeen-Proving-Ground.d553248634999428212-c15.Car-Rental-Guide-Suppliers) - [Book Vacation Homes in Massey on Expedia.com](https://www.expedia.com/Massey-Private-Vacation-Homes.d3000440702-aaPrivateVacationHomes.Travel-Guide-Accommodation)