Kent Area Rentals
From $245 per night (USD)VRBO
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the vi ...
From $245 per night (USD)VRBO
From $456 per night (USD)Expedia
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. W ...
From $456 per night (USD)Expedia
From $279 per night (USD)VRBO
Brand New, Waterfront House on Beautiful Fairlee Creek
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, a ...
From $279 per night (USD)VRBO
From $441 per night (USD)VRBO
3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
At 3 minutes walk to the beach, this Bayfront condo perched on a bluff in beautiful Betterton is a gem the whole year th ...
From $441 per night (USD)VRBO
From $389 per night (USD)VRBO
Historic luxury townhouse in the heart of downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown Welcome to 125 High Street—an exquisitely reno ...
From $389 per night (USD)VRBO
From $313 per night (USD)Expedia
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in t ...
From $313 per night (USD)Expedia
From $4194 per night (USD)VRBO
Bay Cliff: Vacation on the Eastern Shore
- Bedrooms:
- 7
- Bathrooms:
- 13
- Sleeps:
- 30
Enjoy spectacular views of the Chesapeake Bay from an 18-acre property with over 600 feet of waterfront. The magical mai ...
From $4194 per night (USD)VRBO
From $749 per night (USD)Expedia
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BNB Breeze Presents: Langford Estates! Step into your very own, secluded 790-acre sanctuary! This 1864 home has been new ...
From $749 per night (USD)Expedia
From $705 per night (USD)VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $705 per night (USD)VRBO
From $744 per night (USD)VRBO
Breathtaking waterfront home on the Chester River
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated ent ...
From $744 per night (USD)VRBO
From $329 per night (USD)VRBO
All the comforts of home within a 3 Min. walk to the Bay, Restaurants Marinas.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom /2 Full Bath, sleeper sofa and a fully furnished kitchen. Combination Kuerig/Carafe Coffee Maker, Washer/Drye ...
From $329 per night (USD)VRBO
From $266 per night (USD)VRBO
Ruby's Sea Glass Cottage near Betterton Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Have fun with the whole family at this cozy home in the center of Betterton, MD. You can walk to the beach to relax, fi ...
From $266 per night (USD)VRBO
From $583 per night (USD)VRBO
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened ...
From $583 per night (USD)VRBO
From $152 per night (USD)VRBO
Eastern Shore Get Away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Located on Maryland's Eastern Shore, on the Chester River, this fully furnished 1 bedroom, 1 bathroom apartment has all ...
From $152 per night (USD)VRBO
From $343 per night (USD)VRBO
5 bedroom Historic Victorian by Chester River
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...
From $343 per night (USD)VRBO
From $527 per night (USD)Expedia
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire t ...
From $527 per night (USD)Expedia
From $456 per night (USD)VRBO
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recha ...
From $456 per night (USD)VRBO
From $520 per night (USD)VRBO
Waterfront Millington Vacation Rental w/ Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 10
Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...
From $520 per night (USD)VRBO
From $241 per night (USD)VRBO
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" ...
From $241 per night (USD)VRBO
From $688 per night (USD)Expedia
Pet-Friendly Home on Chester River w/ Dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Seasonal Outdoor Pool (May 15-September 15) | Kayaks & Canoe Provided | Crab Traps Calling all waterfront explorers! Lo ...
From $688 per night (USD)Expedia
From $555 per night (USD)VRBO
Welcome to the secluded waterfront oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The cottage has lovely water views from the full kitchen, living room, and a stunning luxurious first floor master suite ...
From $555 per night (USD)VRBO
From $254 per night (USD)Expedia
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the peace and tranquility at "Outrange," Blue Heron Farm's recently updated cabin. While we are new to VRBO, we h ...
From $254 per night (USD)Expedia
From $344 per night (USD)VRBO
Blue Heron Farm Waterfront Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of ...
From $344 per night (USD)VRBO
From $450 per night (USD)VRBO
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 8
Relax with the whole family at this peaceful secluded property. Located on the Chester River in Millington, MD, Pine For ...
From $450 per night (USD)VRBO
From $595 per night (USD)VRBO
The Lazy River House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...
From $595 per night (USD)VRBO