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  • 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

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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.

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