Photo by Jennifer Crim

Search Apartments in Kent Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Apartments in Kent Island and around

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (61)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (25)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Fridge, microwave, oven, stovetop

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (76)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Iron/ironing board, WiFi, bed sheets

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

10.0 out of 10, Exceptional, (22)
"This was the perfect spot for a long weekend. Excellent location and the unit itself was more than we expected. "
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (76)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is €434
includes taxes & fees
19 Aug - 20 Aug
Waterfront Oasis of Annapolis Star
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (95)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is €141
includes taxes & fees
26 Aug - 27 Aug
First Floor Studio Apartment in Historic Chestertown
Downtown furnished apartment - walking distance to restaurants
Interior

Downtown furnished apartment - walking distance to restaurants

10.0 out of 10, Exceptional, (5)
"The home is beautiful and exceptionally maintained! The management of the property is fantastic and they are lovely to work with. They thoughtfully had fresh fruit and some light & healthy munchies in the kitchen when I checked in. The history of the home is also quite interesting! I look forward to a return stay."
Downtown furnished apartment - walking distance to restaurants
Guest quarters at the inn - 205
TV

Guest quarters at the inn - 205

9.2 out of 10, Wonderful, (15)
"Great stay"
Guest quarters at the inn - 205
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (52)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Dean Street's Lower Deck House!
Interior

Dean Street's Lower Deck House!

The price is €395
includes taxes & fees
10 Sept - 11 Sept
Dean Street's Lower Deck House!
The heart of St Michaels awaits.
Exterior

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (46)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
The heart of St Michaels awaits.
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is €259
includes taxes & fees
27 Aug - 28 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (31)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (29)
"Our family loved having this as a short-term rental to visit our midshipman and give him the ability to relax off campus. The owners were communicative and amazing to work with for the entire 3 months! Would absolutely stay here again."
Pristine Downtown 1-Bedroom Steps from State House
Tranquility Awaits
Property grounds

Tranquility Awaits

10.0 out of 10, Exceptional, (19)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (31)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Guest Quarters at the Inn - 103
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 103

9.6 out of 10, Exceptional, (24)
"Very nice room with good accessibility for someone with limited mobility. The room description in Expedia was completely accurate, and we loved the accessibility features. The location is very close to good restaurants that also have good accessibility."
Guest Quarters at the Inn - 103
Guest quarters at the inn - 204
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest quarters at the inn - 204

9.8 out of 10, Exceptional, (14)
"Loved the place! Plenty of room. Hubby and I snuggled in the comfy robes most of the time! Only thing I’d recommend is WiFi for tvs so visitors can log on to their personal streaming apps. "
Guest quarters at the inn - 204
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kent Island Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Food is amazing, service is great and Hotel is beautiful. Always a great experience."
Soo Mi 1-night trip
Posted 1 day ago
The Inn at Chesapeake Bay Beach Club