Kent Island Holiday Rentals from €185: Search Short-Term Rentals

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Our top choices for Kent Island holiday rentals

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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

Stevensville

Anthony P.

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Stevensville

Michael V.

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a red roof, a brick chimney, and a small porch.

3. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveller

includes taxes & fees

3 Nov - 4 Nov

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

includes taxes & fees

1 Dec - 2 Dec

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

5. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

David R.

includes taxes & fees

30 Nov - 1 Dec

A deck with a view of a marina, including boats and docks.

6. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

includes taxes & fees

12 Nov - 13 Nov

A house with a red door, a small porch, and a view of a river with a bridge in the background.

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

West Annapolis

Jill R.

includes taxes & fees

5 Nov - 6 Nov

A hot tub with a white deck and railing, surrounded by trees and a house in the background.

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

Arundel on the Bay

Ryan C.

includes taxes & fees

3 Nov - 4 Nov

A kitchen with a wooden countertop, a stove, and a refrigerator.

9. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Bradford R.

includes taxes & fees

3 Nov - 4 Nov

A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

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

Annapolis

William

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a covered patio, a garage, and a well-maintained lawn.

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

Admiral Heights

Maureen D.

includes taxes & fees

3 Nov - 4 Nov

A waterfront walkway with a brick path, a lamp post, and a bench.

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

Historic District

Nancy N.

includes taxes & fees

30 Nov - 1 Dec

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Edgewater

Kristin G.

includes taxes & fees

3 Nov - 4 Nov

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Edgewater

Diane D.

includes taxes & fees

4 Nov - 5 Nov

Stylish kitchen with open layout and island seating

15. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

16. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

9 Nov - 10 Nov

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

17. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Jennifer H.

includes taxes & fees

3 Nov - 4 Nov

A building with a black metal gate, a brick pathway, and greenery.

18. Secluded Cozy Cottage in Historic Downtown

Historic District

Bridget C.

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

19. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

3 Nov - 4 Nov

A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

20. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Eastport

Michaell M.

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Top Kent Island Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"great location and access to Annapolis"

Hilton Garden Inn Annapolis Downtown

8/10 Good

"I really think when hotels don’t have free parking for their guests, that price should be included in the price of the hotel room. Having to pay an additional $35 is pretty ridiculous….it’s deceiving. Have one price for people who are bringing their own vehicle and one price for people who take other transportation to the hotel."

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent

"To have this amount of waterfront property to include two small beach areas with a circular walking path to and from the house is truly unique. The sunrises over the Chester River are beautiful. The view of water from all three levels is stunning. Very tranquil. The firepit with an abundance of firewood was enjoyed by all. The house has lots of character, and was well stocked with everything you need for an enjoyable stay. Communication with Hal was great from start to finish. Would highly recommend to others."

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10/10 Excellent

"What a great experience!! The hosts couldn't have been kinder, the house and property were beautiful, and the communication was great! They were so responsive, and obviously were working very hard to make sure everyone had a great stay. Tons of room for people to sleep, visit, and hang out. The house is on a huge wooded lot, and the outside was great too. Highly recommend!"

Find out more about Kent Island

Everything you need to know about Kent Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent Island holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent Island holiday rentals we have selected for you start as low as €185 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 holiday 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 holiday.

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.

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Check prices for these dates

Our top choices for Kent Island holiday rentals

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

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

3. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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