USD
en en English
Chestertown
Transport
Metro
Hotels (5)

5 properties found

Show on map

Filters

Clear all filters to see all properties

  • Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    Hotel

    Good

    (242 reviews)

    8
    Highlighting a banquet hall, suited for gatherings, the comfortable Comfort Inn & Suites Chestertown is located nearly 25 minutes' walk from the MassoniArt Gallery. Offering winery tours, the 2-star…

    starts from

    US$ 92 per one night

  • Driftwood Inn

    Driftwood Inn

    Motel

    Average

    (64 reviews)

    4.6
    Nearly 20 minutes' walk from Emmanuel Episcopal Church, the 2-star Driftwood Inn Chestertown includes 18 rooms. With Wi-Fi in public areas, this Chestertown hotel offers 24-hour front desk assistance…

    starts from

    US$ 57 per one night

  • Brampton Inn

    Brampton Inn

    Bed & Breakfast

    Excellent

    (15 reviews)

    9.4
    Featuring Wi-Fi in the rooms, the 5-star Brampton 1860 Bed & Breakfast Chestertown sits 2.8 km from the Cassinelli Winery & Distillery. The hotel entices guests with a car park, available on site.

    starts from

    US$ 337 per one night

  • Lodging At The Imperial

    Lodging At The Imperial

    Hotel
    Situated around 5 minutes' walk from Lodging At The Imperial Hotel Chestertown, guests can reach the Cassinelli Winery & Distillery in no time. Guests who stay at this Chestertown hotel can park…

    starts from

    US$ 194 per one night

  • Inn At Mitchell House

    Inn At Mitchell House

    Hotel
    Inn At Mitchell House Chestertown features 7 rooms and lies 3.8 km from Caulks Field Memorial. Within a 90-minute drive of the hotel, guests can visit Philadelphia.

Change your search parameters to find the hotel you want.

Hotels in Chestertown

With 8 hotels in Chestertown, travelers can choose from cozy boutique inns to modern 5-star accommodations. Most are in the historic downtown district, offering charming ambiance and easy access to local attractions. Average prices hover around $150 for a 3-star and $300 for a 5-star stay. A recently built eco-friendly hotel stands out for its sustainable design. Explore and book now through our platform!

Where to stay in Chestertown - a guide to the best areas and neighborhoods

Hotel Name
Description

Garden Bliss B&B

* The Garden District offers plenty of parks and open spaces for children to play.

* Family-friendly attractions like the Chestertown Botanic Gardens are nearby.

* Residential streets ensure a peaceful and safe environment.

Families will love staying in the Garden District.

Modern Haven

* Midtown offers easy access to major roads and business centers.

* There are several modern hotels equipped with business facilities.

* Dining options are plentiful for quick lunch meetings or dinners.

Business travelers should consider the Midtown area.

Artistry B&B

* The Cultural Arts District buzzes with galleries and events, perfect for exploration.

* It's a great area for networking and meeting fellow travelers with similar interests.

* Many cafés offer free Wi-Fi, perfect for digital nomads.

Solo travelers might enjoy the vibrant Cultural Arts District.

The Old Post Inn

* Historic Downtown's charming streets and cozy restaurants set the perfect romantic scene.

* Plenty of historical sites offer interesting day adventures for couples.

* The town's riverfront views make for idyllic evening walks.

Couples on a romantic getaway should head to the Historic Downtown.

Riverside Retreat

* The River Quarter features several budget-friendly accommodations.

* It's close to nature trails and parks, which are free to explore.

* Public transportation links are conveniently located for easy town navigation.

Budget travelers can find affordable options in the River Quarter.

Chestertown Tips You Must Know

* For the best hotel deals, book during the off-peak months of November to February, avoiding the high prices of the summer and fall festivities.

* Be aware that peak tourist seasons include May for the Chestertown Tea Party Festival and September for the Riverfest, affecting both price and availability.

* If flying in, Baltimore/Washington International Thurgood Marshall Airport is the nearest major airport. From there, renting a car or using local taxis (around $2 per mile) is advisable.

* Save money by dining at local farmer's markets and using the town's free trolley service for sightseeing; check for off-peak museum discounts.

* Exercise caution while exploring unfamiliar or less-populated areas after dark, sticking to well-lit streets in the Historic Downtown.

Frequently asked question

Which hotels offer the best river views in Chestertown?

Riverside Retreat offers spectacular views of the Chester River from almost every room.

Are there any hotels near Chestertown's historic attractions?

The Old Post Inn is just a short walk from several historic attractions, including the Kent County Courthouse.

What hotels are ideal for adventure and outdoor activities?

Staying at Garden Bliss B&B gives you easy access to numerous hiking and biking trails around the area.

When is the best time to enjoy hotel discounts in Chestertown?

The best discounts are generally available during the off-season from November to February.

Are there any hotels that provide easy access to local beaches?

While there's no direct beach in Chestertown, Riverside Retreat offers easy routes to the nearby Sandy Point State Park beach.

Thank you for subscribing
Currency
  • USD U.S. dollar
  • EUR Euro
  • GBP Pound sterling
  • AUD Australian dollar
  • CAD Canadian dollar
  • BRL Brazilian real
  • CNY Chinese yuan
  • CZK Czech koruna
  • DKK Danish krone
  • HKD Hong Kong dollar
  • ILS Israeli new sheqel
  • JPY Japanese yen
  • MYR Malaysian ringgit
  • NZD New Zealand dollar
  • NOK Norwegian krone
  • PLN Polish zloty
  • RON Romanian leu
  • RUB Russian ruble
  • SAR Saudi riyal
  • SGD Singapore dollar
  • ZAR South African rand
  • KRW South Korean won
  • SEK Swedish krona
  • CHF Swiss franc
  • TRY Turkish lira
  • UAH Ukrainian hryvnia
  • THB Thai baht
  • ARS Argentina, Peso
Select language
Check-in
Check-out
Guests
2 guests

Adults:

2

Children:

0