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

Kent Island Vacation Rentals

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Our top choices for Kent Island vacation rentals

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is CA $146
CA $438 total
includes taxes & fees
Nov 23 - Nov 24
Charming Coastal/Country Home w/3 Acres & Sauna!

2. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $120
CA $407 total
includes taxes & fees
Nov 15 - Nov 16
Relax on Kent Island in 4 Bedroom Home w/Waterview

3. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is CA $997
CA $1,797 total
includes taxes & fees
Dec 1 - Dec 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

4. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $997
CA $1,797 total
includes taxes & fees
Dec 1 - Dec 2
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is CA $1,004
CA $1,402 total
includes taxes & fees
Nov 15 - Nov 16
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

6. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is CA $295
CA $673 total
includes taxes & fees
Nov 16 - Nov 17
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

7. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $369
CA $510 total
includes taxes & fees
Nov 22 - Nov 23
Your Annapolis Waterfront retreat for a weekend or any-day getaway!

8. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $385
CA $443 total
includes taxes & fees
Nov 24 - Nov 25
Family Friendly Cozy 3 Bedroom Duplex

9. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is CA $642
CA $1,015 total
includes taxes & fees
Nov 15 - Nov 16
Secluded Cozy Cottage in Historic Downtown

10. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 CA $275
CA $656 total
includes taxes & fees
Nov 15 - Nov 16
Pool Loft Suite | Bay Access & Beach Passes

11. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is CA $307
CA $620 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2br home w/ parking in downtown Annapolis

12. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is CA $333
CA $574 total
includes taxes & fees
Nov 15 - Nov 16
18th Cent. Charm in Historic Downtown Annapolis

13. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $321
CA $751 total
includes taxes & fees
Nov 15 - Nov 16
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

14. 5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
The price is CA $481
CA $863 total
includes taxes & fees
Nov 15 - Nov 16
5 bedroom house with EV charger Near Downtown Annapolis

15. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 CA $275
CA $756 total
includes taxes & fees
Nov 15 - Nov 16
Renovated Bungalow | Walk to Beach | Dog-Friendly

16. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (56 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is CA $546
CA $671 total
includes taxes & fees
Nov 15 - Nov 16
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

17. 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 CA $300
CA $792 total
includes taxes & fees
Dec 15 - Dec 16
Annapolis Retreat - 7 mins from downtown Annapolis!

18. Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!

Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is CA $294
CA $770 total
includes taxes & fees
Nov 15 - Nov 16
Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!

19. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $345
CA $960 total
includes taxes & fees
Nov 15 - Nov 16
Family Home on Mayo Peninsula | Deck | Sleeps 10

20. 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, (35 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $191
CA $418 total
includes taxes & fees
Nov 21 - Nov 22
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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

Find out more about Kent Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kent Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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