Holiday homes & B&B in Chestertown

Holiday rental deals in Chestertown

We have selected the best vacation rentals in Chestertown. Save money with Bluepillow by comparing the best deals from major travel websites in Chestertown

• Chestertown - United States

  from

  101€

  First Floor Studio Apartment in Historic Chestertown

  • 3 Guests · 1Bedroom

  9.7 Exceptional (88)

  Located in Chestertown, this apartment is in a rural area and next to a golf course. Rock Hall Harbor and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those ...

  Check Availability
• Chestertown - United States

  from

  110€

  Secluded Cottage in Middle of Chestertown

  • 2 Guests · 1Bedroom

  6.9 Pleasant (118)

  Offering free WiFi and garden views, Secluded Cottage in Middle of Chestertown is an accommodation set in Chestertown. This apartment features a garden and free private parking. ...

  Check Availability
• Chestertown - United States

  from

  180€

  Newly restored apartment in the heart of Chestertown

  • 4 Guests · 2Bedrooms

  9.6 Exceptional (5)

  This apartment is located in Chestertown. Rock Hall Harbor and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty ...

  Check Availability
• Chestertown - United States

  from

  153€

  Historic Downtown Garden Oasis with Private Patio

  • 3 Guests · 1Bedroom

  Located in Chestertown, this apartment is in the city center. Rock Hall Harbor and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience ...

  Check Availability

Save on Bed & Breakfast in Chestertown

Are you looking for an accommodation in Chestertown and do you want to save money? Choose from 1 Bed & Breakfasts in Chestertown

• Chestertown - United States

  from

  178€

  Brampton Bed and Breakfast Inn

  • Hotel

  8.4 Fabulous (8)

  This 19th century estate is located on Maryland’s Eastern Shore and features lush gardens, outdoor seating, and a large wrap-around terrace with ceiling fans. Chestertown centre is 2 miles away. ...

  Check Availability

Chestertown and the best offers per the best accommodation

What is the best period with the best offers to stay in Chestertown? If you are looking for accommodation in Chestertown during the best period without the chaos of mass tourism, the low season month with the best tariffs is in the month of January. The week with the best prices for that month is the week from 01-07 to 01-14.
If instead you are looking for accommodation in Chestertown during the high season, to enjoy the destination and it's capacities, the month of September is right for you. The most amount of accommodation available at the most convenient price is during the week that spans from from 09-16 to 09-23.
Chestertown is a touristic destination where the accommodation has an average cost of 434 Canadian dollars per night.

• Chestertown: The best accommodation with the best price
• Chestertown: The best holiday apartments at the best cost for a low cost weekend
• Chestertown: Best B&Bs at the most convenient weekly price

The main interest points and what to see in Chestertown during your stay

• The best accommodation near the major interest areas in Chestertown
• The best apartments
• The best B&Bs
• The best Hotels
• The best independent houses
• The best holiday farmhouses
• The best villas
• The best low cost offers for accommodation in Chestertown near the major interest points

Chestertown: What's the weather like?

Nearby cities

• California
• Ocean City
• Hanover
• Baltimore
• Annapolis
• Clinton