A coastal town with a marina, a bridge, and a highway.

Kent Island Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Kent Island holiday rentals

Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (49 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$1,154
HK$2,669 total
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,154
HK$2,728 total
includes taxes & fees
12 Aug - 13 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining

Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"
United States
Hoi C.
The price is HK$5,686
HK$10,209 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Escape with Pool Nature Lover Paradise
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (86 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$2,118
HK$3,880 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront Oasis of Annapolis Star
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is HK$1,961
HK$3,284 total
includes taxes & fees
28 Jul - 29 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is HK$924
HK$2,232 total
includes taxes & fees
28 Jul - 29 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Coffee/tea maker, fridge, microwave, oven

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (10 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,639
HK$4,551 total
includes taxes & fees
2 Aug - 3 Aug
Renovated Bungalow | Walk to Beach | Dog-Friendly
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,502
HK$4,001 total
includes taxes & fees
10 Aug - 11 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Coffee/tea maker, fridge, microwave, oven

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$1,639
HK$3,916 total
includes taxes & fees
1 Aug - 2 Aug
Pool Loft Suite | Bay Access & Beach Passes
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is HK$1,705
HK$3,606 total
includes taxes & fees
19 Aug - 20 Aug
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is HK$1,341
HK$2,950 total
includes taxes & fees
28 Jul - 29 Jul
Large 2 bedroom house with private parking in a nice neighborhood
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,898
HK$5,436 total
includes taxes & fees
28 Jul - 29 Jul
Family Home on Mayo Peninsula | Deck | Sleeps 10
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,412
HK$4,247 total
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is HK$776
HK$1,246 total
includes taxes & fees
3 Aug - 4 Aug
First Floor Studio Apartment in Historic Chestertown
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$1,035
HK$2,521 total
includes taxes & fees
25 Aug - 26 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
Charming Annapolis WaterVIEW Home
Interior

Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is HK$2,996
HK$3,798 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront Home on Marley Creek!
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,569
HK$2,378 total
includes taxes & fees
29 Jul - 30 Jul
BAYSIDE BUNGALOW
Smart TV, stereo

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (18 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is HK$510
HK$867 total
includes taxes & fees
2 Aug - 3 Aug
Lower Level Loft - Adorable Studio Apt. Near BWI
Coffee/tea maker, fridge, microwave, oven

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (16 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is HK$734
HK$1,901 total
includes taxes & fees
3 Aug - 4 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
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.
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Top Kent Island Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The room was clean and the clean up staff provided prompt service when requested!"
Darren 3-night trip
Posted 4 hours ago
Rod 'N' Reel Resort

Find out more about Kent Island

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