Title: Kent Island Vacation Rentals from CA $368: Short-Term Rentals for 2025 | Expedia.ca [Kent Island Travel Guide](https://expedia.ca/Kent-Island.dx553248635077608788)[Hotels in Kent Island](https://expedia.ca/Kent-Island-Hotels.d553248635077608788.Travel-Guide-Hotels)[Flights to Kent Island](https://expedia.ca/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)[Kent Island Car Rentals](https://expedia.ca/Car-Rentals-In-Kent-Island.d553248635077608788.Car-Rental-Guide)[Kent Island Vacation Packages](https://expedia.ca/Kent-Island.d553248635077608788.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/43a9579ca6b27aad6faa82d08f434807.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jennifer Crim # Kent Island 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=553248635077608788&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Kent Island ## Our top choices for Kent Island vacation rentals ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33510000/33508900/33508826/dd69d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33508900/33508826/63fd99b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33508900/33508826/ecab4cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33508900/33508826/9bd6e47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 240' Private Beachfront @Kent Island Love Point - Great for Large Groups stevensville 10/10 Exceptional (193) "We all had wonderful stay at Love point! " [](https://www.expedia.ca/Stevensville-Hotels-240-Private-Beachfront-Kent-Island-Love-Point-Great-For-Large-Groups.h33508826.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/4d0e4029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/bcee5e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/21ea5e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/17ceb4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. Stevensville 10/10 Exceptional (13) "The host was amazing. The property was as described and was perfect for our group. " [](https://www.expedia.ca/Stevensville-Hotels-Woodland-Retreat-On-Kent-Island-5-Beds.h101278078.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) ![2 bedrooms, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/7cf6f375.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) ![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/66000000/65400000/65393500/65393442/a4e7ac6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65400000/65393500/65393442/c47dc30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65400000/65393500/65393442/bd6766c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65400000/65393500/65393442/2cd0f39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Circa 1700 Chesapeake Colonial home on the National Register. Stevensville 9.8/10 Exceptional (56) "We had a wonderful time staying at your farmhouse! We found it easy to navigate to and the house is as charming as ever. We really enjoyed the private pool during the day and walking down to the deep water dock to take in the picturesque scenery in the evenings. Would absolutely stay here again." [](https://www.expedia.ca/Stevensville-Hotels-Circa-1700-Chesapeake-Colonial-Home-On-The-National-Register.h65393442.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/0d1709c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/02bfe381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/fdf0212d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97090000/97083900/97083848/4ad81af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly Stevensville 10/10 Exceptional (53) "My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area" [](https://www.expedia.ca/Stevensville-Hotels-Accessible.h97083848.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) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.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) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.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 (40) "We had a great stay! The property has everything we needed and host was easy to communicate with " CA $115 CA $368 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/949304ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/17709d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/897979fd.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) ### Chesapeake Houseboat Getaway on Kent Island, Maryland Stevensville 9.8/10 Exceptional (41) "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/98000000/97560000/97553100/97553068/c2f460cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/033d6fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/22d8a3b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97560000/97553100/97553068/5d59a8a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 25-50% Off~Private Beach~Hot Tub~Fire Table~ Stevensville 10/10 Exceptional (29) "Excellent property, great communication with the hosts. Quite and relaxing" [](https://www.expedia.ca/Stevensville-Hotels-Chesapeake-Waterfront-With-Hot-Tub.h97553068.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/bb559863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/6beced05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/cfc6a700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/996d9ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy Stevensville 10/10 Exceptional (41) "Loved the location and the pristine condition of the house. " [](https://www.expedia.ca/Stevensville-Hotels-Waterfront-Home-On-The-Chesapeake-Bay-With-Pier-Only-30-Min-From-Naval-Academy.h33691023.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/8ef85715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/11f83fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/7203703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/w906h683x59y0-0dacccf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Waterfront Cottage Stevensville 8.8/10 Excellent (11) "Enjoyed fishing at the pier and sitting on the porch" [](https://www.expedia.ca/Stevensville-Hotels-Chester-River-Waterfront-Cottage.h83759327.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, toys, books](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/bd18dcc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/9a50943e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/13042673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester 10/10 Exceptional (126) "This was a lovely property and the owners are very attentive and communicate well. The location is perfect for peaceful days/evenings enjoying the Bay, and it’s also a perfect launching spot for day trips to other attractions in the Eastern shore and Annapolis. I am very glad we stayed here. " [](https://www.expedia.ca/Chester-Hotels-Waterfront-Home-On-3-Acres-Fish.h33554342.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c9d30e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/afb23ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/0d1878e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! Saint Michaels 9.6/10 Exceptional (120) "We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage." [](https://www.expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/201547af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/585f0b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/302865e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/ba566cbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably Cape Saint Claire 10/10 Exceptional (36) "Fabulous place. We’ll be booking again next year. " [](https://www.expedia.ca/Annapolis-Hotels-Turning-Point-On-The-Little-Magothy-Large-Private-Estate.h103319197.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-608c1c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1198x1y1-8dbb76d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-8b0bbec7.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) ### Cass-N-Reel Luxury Houseboat Grasonville 10/10 Exceptional (38) "We really enjoyed our stay. Looking forward to staying again!" [](https://www.expedia.ca/Grasonville-Hotels-Cass-N-Reel-Luxury-Houseboat.h94672644.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1646h1094x1y0-5465a8de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/3ae18228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w2058h1525x0y1-500a7afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101200000/101190100/101190049/w1296h1091x4y3-c34e5260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. Historic District 9.4/10 Exceptional (14) "Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!" CA $971 CA $1,716 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Annapolis-Hotels-Grand.h101190049.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/3dba8eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/0c67a974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/8a65e5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/54227098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! Historic District 10/10 Exceptional (233) "This was a wonderful historic home to vacation in" [](https://www.expedia.ca/Annapolis-Hotels-Directly-Across-From-Gate-One-Steps-From-The-Waterfront.h34297781.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/ece781ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/c9bc7ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/ea9f1bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112540000/112534600/112534582/e9d5fa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Waterfront Executive Family Home Annapolis with All Amenities Annapolis 7.4/10 Good (3) "Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. " [](https://www.expedia.ca/Annapolis-Hotels-Luxury-Waterfront-Executive-Family-Home-Annapolis-With-All-Amenities.h112534582.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/d7bd9b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/7e1ea789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/a4a9eedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Getaway, Dock Your Boat & Play! Edgewater 10/10 Exceptional (2) "Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. " CA $145 CA $438 total includes taxes & fees Sep 27 - Sep 28 [](https://www.expedia.ca/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106790000/106784900/106784802/206c024c.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/107000000/106790000/106784900/106784802/905ebea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106790000/106784900/106784802/c74f9d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106790000/106784900/106784802/c86df11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Downtown Annapolis. Stroll to all the Historic District has to offer. Murray Hill 10/10 Exceptional (28) "Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit." [](https://www.expedia.ca/Annapolis-Hotels-Charming-Downtown-Annapolis-Stroll-To-All-The-Historic-District-Has-To-Offer.h106784802.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484012/2805f849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484012/33ccf6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484012/437108b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484012/209add81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! ! Pasadena 9.4/10 Exceptional (89) "This property was a great place for a family to all relax together, play games, and enjoy the water!" [](https://www.expedia.ca/Pasadena-Hotels-Firepit.h33484012.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=2025-10-09&endDate=2025-10-10®ionId=553248635077608788&adults=2&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%2FKent-Island-Vacation-Rentals.d553248635077608788.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FKent-Island-Vacation-Rentals.d553248635077608788.Travel-Guide-VacationRentals) ## Top Kent Island Hotel Reviews ![Microtel Inn & Suites by Wyndham Gambrills](//images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg) ### Microtel Inn & Suites by Wyndham Gambrills 10/10 Excellent "It was great accommodation. The only thing we didn't like was the pillow were not comfortable at all. Too soft and you head just sunk in. Other than that it was great. Room smelled clean and everything was very nice. " [](https://expedia.ca/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Courtyard by Marriott Annapolis](//images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "Extremely cozy. Felt good to just relax." [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.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 "Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "My wife and were away to celebrate our 34th wedding anniversary and the stay was close to home affordable and very comfortable. Hotel staff was very friendly and welcoming " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "No additional comment. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "I was perfect for our visit. Close to everything." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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 "Stayed for one night; room was nice, easy to access, and located near numerous local attractions. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Room was very clean, bed was extremely comfortable!!! Modest hotel but well worth the money! Breakfast was awesome!!! Highly recommended! Will stay here again!" [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![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 "we loved the view and the room" [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ## Find out more about Kent Island **Everything you need to know about** **Kent Island** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kent Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Kent Island vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Kent Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kent Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent Island vacation rentals we have selected for you start as low as CA $368 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Kent Island rentals** At Expedia, we put the best Kent Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Kent Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kent Island vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kent Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Kent Island ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)