Photo by Julie Miller

Hotels with Parking in Chestertown

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Apr 2 - Apr 3
Tomorrow
Apr 3 - Apr 4
This weekend
Apr 4 - Apr 6
Next weekend
Apr 11 - Apr 13

Hotels with Parking in Chestertown

Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
9.0 out of 10, Wonderful, (87)
The price is $248
includes taxes & fees
$223 per night
Apr 4 - Apr 5
Friends Lake Inn
Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
Pine Tree Motel & Cabins
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
The price is $652
includes taxes & fees
$587 per night
Apr 14 - Apr 15
The Fern Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top landmarks in Chestertown

Friends Lake

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.

See properties in Friends Lake
Friends Lake

Loon Lake

Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.

See properties in Loon Lake
Loon Lake

Loon Lake Beach

If you can't wait to get to the beach, you might enjoy a trip to Loon Lake Beach located 2 mi (3.3 km) from central Chestertown.

See properties in Loon Lake Beach
Loon Lake Beach

Frequently asked questions

What are the best hotels with parking in Chestertown?
One of the leading Chestertown hotels with parking based on guest reviews is Highlands Castle Overlooking Lake George. . Plus 2 Other Castles. Make the most of hypo-allergenic bedding and a lake view. Or set your GPS for Pine Tree Motel & Cabins, another top-rated option with a place for your vehicle. Want free parking in Chestertown? Check the hotel listing to find out if it’s included.
What are the cheapest hotels with parking in Chestertown?
Staying at a cheap hotel in Chestertown with parking makes sticking to your budget a breeze. Rest up in between exploring the sights at Pine Tree Motel & Cabins, which offers individually decorated rooms and a yard.
What is the best time to stay in a hotel with parking in Chestertown?
When deciding when to stay in a hotel with parking in Chestertown, consider the tourist seasons, weather and local events. These will often impact costs, crowds and the experiences you’ll have. Also, think about your travel preferences, including whether you prefer lively peak times or quieter months.
What hotels with parking are closest to Loon Lake Beach?
Just a short drive from Loon Lake Beach, Pine Tree Motel & Cabins is one of the closest hotels with parking. Take advantage of a yard and a firepit here. Another option nearby is The Loft at The Remington. Stay in a hotel in Chestertown with parking and come and go as you please.
Are there any hotels in Chestertown with free parking?
Parking is on the house at HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!. This hotel has a lake view and hypo-allergenic bedding. Pine Tree Motel & Cabins has free parking too. If you want to see what else is available, check out the 1,471 Chestertown hotels with parking.