46+ Vacation Rentals Near Historical Society of Kent County Maryland |
  1. USA
  2. Maryland
  3. Chestertown
  4. Historical Society of Kent County Maryland

Sonoma Villas - Vacation Rentals in Historical Society of Kent County Maryland

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! From US $537
         

10.0 (90 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Brampton 1860 From US $397
         

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

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Comfort Inn & Suites Chestertown From US $119
         

8.6 (929 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Wren Retweet- Country Estate in Center of C’Town From US $552
         

10.0 (75 Reviews)
House
Wren Retweet- Country Estate in Center of C’Town
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Home on Chester River w/Dock! From US $799
         

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New
House
Pet-Friendly Home on Chester River w/Dock!
  • Parking
  • Pet Friendly
  • Pool

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Red Roof Inn & Suites Chestertown From US $75
         

7.2 (464 Reviews)
Hotel
Red Roof Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Historic Downtown Garden Oasis with Private Patio From US $227
         

10.0 (54 Reviews)
Apartment
Historic Downtown Garden Oasis with Private Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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3 Mi to Washington College! Updated Home w/Patio From US $330
         

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New
House
3 Mi to Washington College! Updated Home w/Patio
  • Parking
  • Balcony/Terrace
  • Security/Safety

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Harbor View Haven | Waterfront w/Hot Tub + Dock! From US $618
         

10.0 (31 Reviews)
House
Harbor View Haven | Waterfront w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • TV

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Lovely Home in Chestertown - Free EV Charging for guests From US $291
         

10.0 (27 Reviews)
House
Lovely Home in Chestertown - Free EV Charging for guests
  • Air Conditioner
  • Parking
  • TV

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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown From US $545
         

10.0 (6 Reviews)
House
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
  • Air Conditioner
  • Parking
  • TV

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Newly restored apartment in the heart of Chestertown From US $385
         

9.8 (29 Reviews)
Apartment
Newly restored apartment in the heart of Chestertown
  • Air Conditioner
  • Parking
  • TV

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Beautiful, spacious waterfront home, an easy walk to historic Chestertown From US $1,658
         

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

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First Floor Studio Apartment in Historic Chestertown From US $159
         

9.6 (116 Reviews)
Apartment
First Floor Studio Apartment in Historic Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Home on Chester River w/Dock! From US $1,030
         

9.6 (23 Reviews)
House
Pet-Friendly Home on Chester River w/Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Riverside at Pear Tree Point-Waterfront Escape From US $468
         

New
House
Riverside at Pear Tree Point-Waterfront Escape
  • Air Conditioner
  • Parking
  • TV

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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown From US $662
         

10.0 (111 Reviews)
House
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

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Victorian Hideaway: Beautiful Exterior, Modern interior From US $642
         

9.8 (24 Reviews)
House
Victorian Hideaway: Beautiful Exterior, Modern interior
  • Air Conditioner
  • Parking
  • TV

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Circa 1900 Home in the Heart of Historic Downtown Chestertown From US $383
         

10.0 (87 Reviews)
House
Circa 1900 Home in the Heart of Historic Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

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Breathtaking waterfront home on the Chester River From US $945
         

10.0 (40 Reviews)
House
Breathtaking waterfront home on the Chester River
  • Air Conditioner
  • Parking
  • Pool

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The Lazy River House From US $622
         

10.0 (14 Reviews)
House
The Lazy River House
  • Air Conditioner
  • Parking
  • TV

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Charming Chestertown Waterfront Cottage From US $459
         

10.0 (60 Reviews)
House
Charming Chestertown Waterfront Cottage
  • Air Conditioner
  • Parking
  • TV

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Owl Cottage From US $200
         

10.0 (11 Reviews)
Cottage
Owl Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park! From US $666
         

10.0 (4 Reviews)
House
Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park!
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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★ Pro Tip: Sonomavillas makes it easy to compare the best listings on Sonomavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sonomavillas 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 Historical Society of Kent County Maryland.

Weather in Historical Society of Kent County Maryland

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

December - February
High 56°F       Low 33°F
March - May
High 73°F       Low 38°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 42°F

Top Attractions Around Historical Society of Kent County Maryland, MD

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


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 Morgan State University

Historical Society of Kent County Maryland Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Historical Society of Kent County Maryland?

Currently, the total number of properties listed in 2026 is over 46 in the Historical Society of Kent County Maryland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historical Society of Kent County Maryland.