Kent Island holiday rentals

We found 1,006 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Kent Island

Showing deals for:29 Jan - 5 Feb

Interior
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

8% off
S$10,932
for 7 nights, 1 home
S$1,562 per night
includes taxes & fees
Sunset Lodge on the Bay
Kitchen
Exceptional
(18 reviews)

House near Patapsco River 2700 square feet

Pasadena

8% off
S$8,435
for 7 nights, 1 home
S$1,205 per night
includes taxes & fees
House near Patapsco River 2700 square feet
Terrace/patio
Exceptional
(5 reviews)

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Stevensville

16% off
S$6,522
for 7 nights, 1 home
S$932 per night
includes taxes & fees
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
The owners enjoy the local wildlife. Local osprey  & herons are always fishing.
Exceptional
(75 reviews)

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

Stevensville

8% off
S$7,554
for 7 nights, 1 home
S$1,079 per night
includes taxes & fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Marina
Exceptional
(72 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville

9% off
S$2,416
for 7 nights, 1 houseboat
S$345 per night
includes taxes & fees
Chesapeake Houseboat Getaway on Kent Island, Maryland
vista from the great room!
Exceptional
(145 reviews)

Million Dollar View of the Chesapeake Bay

Deale

7% off
S$3,519
for 7 nights, 1 home
S$503 per night
includes taxes & fees
Million Dollar View of the Chesapeake Bay
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
Exceptional
(50 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

11% off
S$7,996
for 7 nights, 1 home
S$1,142 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
The view off of the point, breathtaking.
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
S$6,358
for 7 nights, 1 home
S$908 per night
includes taxes & fees
Grandview- Main House
Large, beautifully updated kitchen area is perfect for meal times.
Exceptional
(39 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
S$8,277
for 7 nights, 1 home
S$1,182 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
3rd Floor Dorm 2/3 - Far corner of U-shaped room.  Bathroom on right.
Exceptional
(220 reviews)

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

Stevensville

20% off
S$3,980
for 7 nights, 1 home
S$569 per night
includes taxes & fees
240' Private Beachfront @Kent Island Love Point - Great for Families
Terrace/patio
Exceptional
(95 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

7% off
S$5,084
for 7 nights, 1 home
S$726 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
New Kitchen 2022
Exceptional
(67 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
S$4,085
for 7 nights, 1 home
S$584 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Living area
Exceptional
(8 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

7% off
S$10,501
for 7 nights, 1 home
S$1,500 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Exterior
Exceptional
(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

8% off
S$7,507
for 7 nights, 1 home
S$1,072 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Cottage Bathroom
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
S$17,612
for 7 nights, 1 home
S$2,516 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Kitchen
Exceptional
(33 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

11% off
S$2,667
for 7 nights, 1 room
S$381 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
In Stevensville MD 5 miles to Chesapeake Bay Bridge. 20 miles o Annapolis.
Exceptional
(44 reviews)

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

Stevensville

8% off
S$7,536
for 7 nights, 1 home
S$1,077 per night
includes taxes & fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Private kitchen
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
S$6,225
for 7 nights, 1 home
S$889 per night
includes taxes & fees
Arcadia Shores on the Cove.
Property grounds
Exceptional
(95 reviews)

Chesapeake Bay Cottage

Churchton

8% off
S$3,250
for 7 nights, 1 cottage
S$464 per night
includes taxes & fees
Chesapeake Bay Cottage
Private kitchen
Exceptional
(15 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

7% off
S$6,670
for 7 nights, 1 home
S$953 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Exceptional
(148 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
S$7,738
for 7 nights, 1 home
S$1,105 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Front gardens
Exceptional
(65 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
S$2,874
for 7 nights, 1 home
S$411 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!
Living area
Exceptional
(12 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
S$5,410
for 7 nights, 1 home
S$773 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Enjoy screened in porch with dining table and sitting area
Exceptional
(64 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

7% off
S$5,017
for 7 nights, 1 home
S$717 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
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Explore the waterfront setting in Kent Island

Enjoy the history and other features of Kent Island. Well known for its island views, boating and cycling, this relaxing city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Kent Island

Do you want to discover attractions to visit in the area? Venture out of your holiday home and check out everything that Kent Island has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (9.4 mi / 15.1 km)
  • Bay Hills Golf Club (11 mi / 17.7 km)
  • St. Michaels Winery (12.2 mi / 19.7 km)
  • Maryland Renaissance Festival (14.6 mi / 23.5 km)
  • Thanksgiving Farm Wines (16.7 mi / 26.8 km)
  • Chesapeake Beach Water Park (20.3 mi / 32.6 km)

Exploring the natural features in Kent Island

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Kent Island is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Northern Chesapeake Bay (2.1 mi / 3.4 km)
  • Sandy Point Beach (6.3 mi / 10.1 km)
  • Bay Ridge Beach (6.9 mi / 11.1 km)
  • Eastern Neck National Wildlife Refuge (8.6 mi / 13.9 km)
  • Maryland Quiet Waters Park (9.1 mi / 14.6 km)
  • Fort Smallwood Park (16.5 mi / 26.6 km)

Frequently asked questions

What is the best area to stay in Kent Island when booking a holiday rental?
One of the more sought-after areas for a Kent Island holiday home is Chester. When you lock in your holiday rental with Vrbo, you'll have the entire place to yourself. This means you don't have to share it with anyone apart from your group.
What is the most popular type of holiday rental accommodation in Kent Island?
Houses are the most popular style of holiday rental in Kent Island, according to our data. Even if you have something else in mind, Vrbo has holiday homes in many sizes and shapes. Filter our options to find your perfect match.
How much does it cost to rent a holiday rental in Kent Island?
The average price for a holiday home in Kent Island is based on several factors, such as property type, season and length of stay. Whether you prefer a villa with space for extended family or a cosy condo perfect for just you and the kids, just enter your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Kent Island?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Kent Island travel dates to view your options on Vrbo. Can't live without a private pool? Use the filters to pick the features and amenities you want in your beach house.
What are popular rental amenities in Kent Island?
The most popular rental amenities people search for in Kent Island include an ocean view, a water view and an electric car charging station. Whether you're on the road with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people that matter most.
Can I find two-bedroom holiday rentals in Kent Island?
Take off with your besties and enjoy total privacy and comfort in one of the three two-bedroom holiday properties Kent Island has to offer.
Are there holiday rentals with WiFi in Kent Island?
Kent Island has 23 holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Vrbo homes will keep you online.
How old do you have to be to rent a holiday rental in Kent Island?
The minimum age allowed can vary across properties on Vrbo, so be sure to look at the rules of the holiday rental in Kent Island you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Kent Island for?
The length of time you can rent a holiday rental in Kent Island differs according to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With tons of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to discover somewhere just right to call your home away from home in Kent Island.

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