Bespoke Usa Travel - Vacation Rentals in Chestertown

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

The Lodge at Great Oak Landing From US $126
         

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8.0 (76 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! From US $501
         

Country Estate in Historic District From US $384
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Downtown Garden Oasis with Private Patio From US $169
         

10.0 (43 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Chestertown

Over 56+ Luxury Places to Stay in or Near Chestertown
Thornton From US $1,758
         

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New
House
  • Parking
  • Pet Friendly
  • Pool
Historic Manor House on Beautiful Eastern Shore Estate From US $1,283
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Breathtaking waterfront home on the Chester River From US $764
         

Pet-Friendly Home on Chester River w/Dock! From US $683
         

9.6 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Chestertown

Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Chestertown
First Floor Studio Apartment in Historic Chestertown From US $131
         

9.6 (108 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Chestertown From US $113
         

8.6 (857 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Chestertown From US $124
         

8.0 (232 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Private pier and pool at this waterfront Chestertown home From US $1,166
         

9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Chestertown

Over 17+ Pet-Friendly Vacation Rentals in or Near Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! From US $221
         

Red Roof Inn & Suites Chestertown From US $80
         

7.2 (419 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Owl Cottage From US $200
         

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

Large Vacation Homes & Villas in Chestertown

Over 9+ Large Vacation Homes & Villas in or Near Chestertown
Brampton 1860 From US $199
         

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9.6 (19 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
River Lodge, Casual Riverfront setting From US $729
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Chestertown Varoom and Airbnb Places to Stay Under $200

Over 4+ Chestertown Varoom and Airbnb Places to Stay Under $200
2 Beds, 2.5 Baths, Perfect Downtown Location From US $170
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Driftwood Inn From US $70
         

5.2 (175 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Cottage within walking distance to the Bay! From US $191
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • TV
  • Balcony/Terrace
Carriage House Hideaway in Middle of Chestertown From US $136
         

10.0 (97 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Chestertown

Over 10+ Instantly Bookable Vacation Homes in or Near Chestertown
Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park! From US $480
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Newly restored apartment in the heart of Chestertown From US $293
         

River Cottage, Chestertown From US $267
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Blue Heron Farm Waterfront Chalet From US $322
         

10.0 (1 Review)
Other
  • Air Conditioner
  • Parking
  • TV

About Chestertown Vacation Rentals

With more than 65 Chestertown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chestertown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Chestertown, 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 Chestertown. Places to stay near Chestertown are 967.56 ft² on average, with prices averaging $512 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Chestertown 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 Chestertown

Type Count
Vacation Homes 44
Holiday Apartments 8
Hotels with Suites 5
Cottages 3
Cabin Rentals 2
Others 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Chestertown

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel 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 Chestertown.

Weather in Chestertown

View the weather forecast for Chestertown before booking your Chestertown 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