1+ Vacation Rentals Near Kent County |
  1. USA
  2. Maryland
  3. Kent County

Lakes Resorts - Vacation Rentals in Kent County

Inn at Haven Harbour From US $350
         

6.4 (27 Reviews)
Resort
Inn at Haven Harbour
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Kent County Vacation Rentals

Luxury Places to Stay in Kent County

Over 174+ Luxury Places to Stay in or Near Kent County
Thornton From US $1,758
         

|
New
House
Thornton
  • Parking
  • Pet Friendly
  • Pool

View Availability
Historic Manor House on Beautiful Eastern Shore Estate From US $1,260
         

10.0 (27 Reviews)
House
Historic Manor House on Beautiful Eastern Shore Estate
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler From US $1,258
         

9.8 (24 Reviews)
House
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
  • Air Conditioner
  • Parking
  • Pool

View Availability
A stunning Chesapeake Bay sunset from a beautiful home with an inground pool! From US $1,214
         

New
House
A stunning Chesapeake Bay sunset from a beautiful home with an inground pool!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna From US $1,212
         

9.8 (40 Reviews)
Villa
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
  • Air Conditioner
  • Parking
  • Pool

View Availability
Sunset Lodge on the Bay From US $1,120
         

10.0 (44 Reviews)
House
Sunset Lodge on the Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
Beautiful, spacious waterfront home, an easy walk to historic Chestertown From US $1,069
         

9.8 (23 Reviews)
House
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
  • Air Conditioner
  • Parking
  • TV

View Availability
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock From US $1,025
         

10.0 (61 Reviews)
House
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Kent County Luxury Vacation Rentals
Find More Kent County Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Kent County

Over 30+ Top-Rated Vacation Rentals with a Pool in or Near Kent County
Eastern Shore beach cottage get-away From US $327
         

10.0 (139 Reviews)
Cottage
Eastern Shore beach cottage get-away
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Waterfront Paradise on the Eastern Shore of Chesapeake Bay From US $911
         

10.0 (73 Reviews)
House
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
  • Air Conditioner
  • Parking
  • Pool

View Availability
Waterfront w/private pier, pool, Hot Tub, kayaks and in town. From US $505
         

10.0 (62 Reviews)
House
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Inn at Huntingfield Creek From US $173
         

|
10.0 (59 Reviews)
Bed & Breakfast
Inn at Huntingfield Creek
  • Air Conditioner
  • Parking
  • Pool

View Availability
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining From US $250
         

10.0 (50 Reviews)
House
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Breathtaking waterfront home on the Chester River From US $749
         

10.0 (38 Reviews)
House
Breathtaking waterfront home on the Chester River
  • Air Conditioner
  • Parking
  • Pool

View Availability
BEACH WITHOUT THE BUSTLE From US $220
         

10.0 (36 Reviews)
Condo
BEACH WITHOUT THE BUSTLE
  • Air Conditioner
  • Parking
  • Pool

View Availability
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. From US $380
         

10.0 (7 Reviews)
Cottage
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Kent County Vacation Rentals with a Pool

Pet-Friendly Vacation Rentals in Kent County

Over 61+ Pet-Friendly Vacation Rentals in or Near Kent County
200 steps to the beach! From US $333
         

10.0 (93 Reviews)
House
200 steps to the beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Chestertown Family Hideaway with Kayaks and Deck! From US $291
         

|
New
House
Chestertown Family Hideaway with Kayaks and Deck!
  • Parking
  • Pet Friendly
  • Wheelchair Accessible

View Availability
Red Roof Inn & Suites Chestertown From US $80
         

7.2 (426 Reviews)
Hotel
Red Roof Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! From US $527
         

10.0 (85 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Country Estate in Historic District From US $384
         

10.0 (70 Reviews)
House
Country Estate in Historic District
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
WATERFRONT right on a BEACH From US $604
         

10.0 (51 Reviews)
House
WATERFRONT right on a BEACH
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
This is truly a Baydream! From US $270
         

10.0 (35 Reviews)
House
This is truly a Baydream!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Entire Townhouse in Rock Hall From US $203
         

10.0 (34 Reviews)
House
Entire Townhouse in Rock Hall
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Pet-Friendly Vacation Rentals in Kent County on PetFriendly.io

Large Vacation Homes & Villas in Kent County

Over 41+ Large Vacation Homes & Villas in or Near Kent County
Harbor View Haven | Waterfront w/Hot Tub + Dock! From US $448
         

10.0 (27 Reviews)
House
Harbor View Haven | Waterfront w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • TV

View Availability
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office From US $428
         

10.0 (1 Review)
House
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD From US $427
         

10.0 (21 Reviews)
House
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
  • Air Conditioner
  • Parking
  • TV

View Availability
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11 From US $304
         

10.0 (20 Reviews)
House
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
  • Air Conditioner
  • Parking
  • TV

View Availability
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets From US $716
         

10.0 (8 Reviews)
House
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Grays Inn Creek Waterfront Pvt. Dock Kayaks & View From US $533
         

10.0 (2 Reviews)
House
Grays Inn Creek Waterfront Pvt. Dock Kayaks & View
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Waterfront! Private Dock, Boat Tie-Up & Near Town From US $238
         

10.0 (2 Reviews)
House
Waterfront! Private Dock, Boat Tie-Up & Near Town
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach From US $374
         

9.8 (46 Reviews)
House
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Family Vacation Rentals in Kent County on FVR

Wheelchair Accessible Vacation Homes in Kent County

Over 3+ Wheelchair Accessible Vacation Homes in or Near Kent County
Stay in the landmark Lighthouse! From US $373
         

10.0 (108 Reviews)
House
Stay in the landmark Lighthouse!
  • Air Conditioner
  • Parking
  • TV

View Availability
Comfort Inn & Suites Chestertown From US $124
         

8.0 (232 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Comfort Inn & Suites Chestertown From US $113
         

8.6 (866 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Properties

Kent County Varoom and Airbnb Places to Stay Under $200

Over 18+ Kent County Varoom and Airbnb Places to Stay Under $200
Historic Downtown Garden Oasis with Private Patio From US $169
         

10.0 (43 Reviews)
Apartment
Historic Downtown Garden Oasis with Private Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

View Availability
Brampton 1860 From US $199
         

|
9.6 (19 Reviews)
Bed & Breakfast
Brampton 1860
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
The Lodge at Great Oak Landing From US $126
         

|
7.8 (77 Reviews)
Cabin
The Lodge at Great Oak Landing
  • Air Conditioner
  • Parking
  • Pool

View Availability
First Floor Studio Apartment in Historic Chestertown From US $159
         

9.6 (108 Reviews)
Apartment
First Floor Studio Apartment in Historic Chestertown
  • Air Conditioner
  • Parking
  • Pool

View Availability
Guest Suite for up to 2 in a Victorian on the Chester River From US $78
         

9.6 (19 Reviews)
Apartment
Guest Suite for up to 2 in a Victorian on the Chester River
  • Air Conditioner
  • Parking
  • TV

View Availability
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland. From US $170
         

8.6 (4 Reviews)
House
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
High Tide Haven Suite From US $200
         

New
House
High Tide Haven Suite
  • Air Conditioner
  • TV
  • View

View Availability
Carriage House Hideaway in Middle of Chestertown From US $190
         

10.0 (101 Reviews)
Apartment
Carriage House Hideaway in Middle of Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Kent County Vacation Rental Deals

Instantly Bookable Vacation Homes in Kent County

Over 62+ Instantly Bookable Vacation Homes in or Near Kent County
Contemporary waterfront house with private dock & kayaks! From US $319
         

10.0 (66 Reviews)
House
Contemporary waterfront house with private dock & kayaks!
  • Air Conditioner
  • Parking
  • TV

View Availability
Circa 1900 Home in the Heart of Historic Downtown Chestertown From US $331
         

10.0 (78 Reviews)
House
Circa 1900 Home in the Heart of Historic Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

View Availability
BAYSIDE BUNGALOW From US $297
         

10.0 (52 Reviews)
House
BAYSIDE BUNGALOW
  • Air Conditioner
  • Parking
  • View

View Availability
Overton Farm Cottage From US $261
         

10.0 (35 Reviews)
House
Overton Farm Cottage
  • Air Conditioner
  • Parking
  • TV

View Availability
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise! From US $259
         

10.0 (29 Reviews)
House
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
  • Air Conditioner
  • Parking
  • TV

View Availability
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest From US $206
         

10.0 (19 Reviews)
House
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
  • Air Conditioner
  • Parking
  • TV

View Availability
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! From US $294
         

10.0 (17 Reviews)
Apartment
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
  • Air Conditioner
  • Parking
  • TV

View Availability
Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay From US $383
         

10.0 (15 Reviews)
House
Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Kent County Short-Term Vacation Rentals

About Kent County Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Kent County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kent County. Places to stay near Kent County are 483.44 ft² on average, with prices averaging $350 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Kent County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kent County

Type Count
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Kent County

★ Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kent County.

Weather in Kent County

View the weather forecast for Kent County before booking your Kent County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Kent County, MD

Lakesresorts offers a large selection of top attractions around Kent County. Research things to do on your vacation before you visit Kent County.


Washington College The Mainstay Wilmer Park Eastern Neck National Wildlife Refuge Rock Hall Harbor Historical Society of Kent County Maryland River Arts Chestertown Betterton Beach Garfield Center for the Arts at the Prince Theater Crow Farm and Vineyard Ferry Park National Aquarium in Baltimore Baltimore Cruise Terminal Baltimore Convention Center Johns Hopkins Hospital Horseshoe Casino Baltimore Baltimore Inner Harbor Marina M&T Bank Stadium Oriole Park at Camden Yards Dover International Speedway Dover Downs Casino U.S. Naval Academy Ripken Stadium Power Plant Live Hippodrome Theatre Baltimore Museum of Art University of Maryland - Baltimore Delaware State University White Marsh Mall Westfield Annapolis Mall

Other Places to Stay Near Kent County, MD


Great Oak Landing 193 Properties Crow Farm and Vineyard 123 Properties Galena 93 Properties Eastern Neck National Wildlife Refuge 87 Properties Tolchester Beach 83 Properties Edesville 78 Properties Rock Hall 61 Properties Millington 54 Properties Chestertown 45 Properties Kennedyville 29 Properties Still Pond 28 Properties Betterton 27 Properties