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Chestertown (NY) hotels and places to stay

Search among 23 available hotels and places to stay in Chestertown from 50+ providers.

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12Aug2022Friday
13Aug2022Saturday
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  • The inn has
    • Free Wi-Fi in public areas
  • The inn has
    • On-site car park
  • The inn has
    • 24-hour reception
View on map2.7 mi from City Center2.6 mi from City Center
The hotel overlooks the garden and offers American cuisine, boasting location in a natural area.
8.8
Great1 review
From   US$ 199 /nightSelect
Not available
Bed & Breakfast
  • The bed & breakfast has
    • Free Wi-Fi in rooms
  • The bed & breakfast has
    • On-site car park
  • The bed & breakfast has
    • Bar/ Lounge area
    • Outdoor dining area
  • The bed & breakfast has
    • Fitness centre
View on map3.3 mi from City Center3.1 mi from City Center
Featuring a sports bar plus an unforgettable view of the mountain, the venue is located in a busy area just off a boat dock.
8.8
Great17 reviews
From   US$ 523 /nightSelect
Not available
11 adults
4 bedrooms
4 beds
500 yd from City Center100 yd from City Center
Up Yonda Farm is 15 km from this villa that offers 6 bedrooms along with a full kitchen.
From   US$ 676 /nightSelect
Not available
2.1 mi from City Center2.2 mi from City Center
The hotel offers a budget accommodation with 8 rooms in the beach area of Chestertown.
7.4
Very good4 reviews
From   US$ 158 /nightSelect
Not available
6 adults
4 bedrooms
4 beds
4.1 mi from City Center
Offering a kitchen complete with a microwave oven, a dishwasher and coffee/tea making facilities, this villa is located close to Circle B Ranch.
From   US$ 219 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
2.1 mi from City Center2.2 mi from City Center
Circle B Ranch is 7 km from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 152 /nightSelect
Not available
7 adults
4 bedrooms
5 beds
2.8 mi from City Center2.9 mi from City Center
Offering a fully-fitted kitchen complete with a dishwasher, coffee/tea makers and a stove, this villa is located close to Rustic Charm.
From   US$ 735 /nightSelect
Not available
8 adults
3 bedrooms
4 beds
3.4 mi from City Center
Prospect Mountain is 30 km from this villa that offers 3 bedrooms along with a fully-fitted kitchen.
From   US$ 209 /nightSelect
Not available
10 adults
5 bedrooms
7 beds
3.5 mi from City Center
Situated a 20-minute drive to Rustic Charm, this villa features the balcony and a patio.
From   US$ 615 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
2.2 mi from City Center2.3 mi from City Center
Rustic Charm is 3.8 km from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 536 /nightSelect
Not available
6 adults
3 bedrooms
4 beds
3.7 mi from City Center
Rustic Charm is 6 km from this villa that offers 3 bedrooms along with a full kitchen.
From   US$ 410 /nightSelect
Not available
14 adults
4 bedrooms
5 beds
3.5 mi from City Center
Featuring a play area and a playground which are perfect for kids, this villa is situated 6 km away from the city centre.
From   US$ 466 /nightSelect
Not available
6 adults
3 bedrooms
4 beds
3.5 mi from City Center
Featuring a play area and a playground which are perfect for kids, this villa is situated 6 km away from the city centre.
From   US$ 282 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
2.4 mi from City Center2.5 mi from City Center
Situated 2.5 miles from Rustic Charm, the vacation home offers snorkeling, canoeing and diving.
From   US$ 391 /nightSelect
Not available
Villa
8 adults
4 bedrooms
4 beds
3.0 mi from City Center2.8 mi from City Center
Located about 2.8 miles from Loon Lake Public Beach, the vacation home offers accommodation for 8 guests.
From   US$ 334 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
3.6 mi from City Center
Featuring a games room and a playroom which are perfect for kids, this villa is situated 3.4 miles away from the city center.
From   US$ 209 /nightSelect
Not available
9.6 mi from City Center
This villa is a 10-minute drive from North Creek Baptist Church and offers snorkeling, diving and bowling.
From   US$ 430 /nightSelect
Not available
2.6 mi from City Center2.7 mi from City Center
Situated 2.5 miles from Dynamite Hill Recreation Area, the villa offers snow skiing, hiking and horse riding.
From   US$ 239 /nightSelect
Not available
4.7 mi from City Center
View is 1.6 miles from this villa that offers 2 bedrooms along with a fully-fitted kitchen.
From   US$ 395 /nightSelect
Not available
4.7 mi from City Center
This villa is a 10-minute drive from Loon Lake Public Beach and offers snorkeling, diving and snow skiing.
From   US$ 191 /nightSelect
Not available
3.6 mi from City Center
Loon Lake Public Beach is 2 miles from this villa that offers 3 bedrooms along with a kitchen.
From   US$ 207 /nightSelect
Not available
700 yd from City Center700 yd from City Center
Being within 0.5 miles of Rustic Charm, this villa features a shared lounge.
From   US$ 277 /nightSelect
Not available
2 adults
1 bedroom
2 beds
3.6 mi from City Center
Situated a 20-minute drive to Natural Stone Bridge and Caves, this villa features the garden and a sunny patio.
From   US$ 197 /nightSelect
Not available

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23 hotels found

FAQs about hotels in Chestertown

We hope that the answers to these questions will help you plan your trip

What are the best cheap hotels in Chestertown?

Conways Lake Manor rated 7.0/10 is great for your budget stay in Chestertown. This property has a picnic area, a golf course and fishing. To check more cheap hotels click here.

What are the top 5-star hotels in Chestertown?

The best one is Friends Lake Inn rated 8.8/10 at the cost of 301US$ per night with meals, a swimming pool and various massages. To see more favored 5-star hotels click here.

What are the top Chestertown hotels for couples?

According to Booked.net travel data, there are 3 deals for couples. The Fern Lodge rated 8.8/10 is a favorite 4-star hotel for couples, featuring snow skiing, a playroom and hiking. Travelers can book a room at this property for about 523US$ per night. Friends Lake Inn with rating 8.8/10 is also a perfect 5-star property for couples with meals, a swimming pool and various massages. It also has a swimming pool and an outdoor pool and offers rooms for about 301US$ per night. Go here to check more romantic accommodations.

What are the most favored hotels in Chestertown?

You may book The Fern Lodge rated 8.8/10 with snow skiing, a playroom and hiking. It costs 523US$ per night. Also, you may book Friends Lake Inn (rating: 8.8/10), a fantastic hotel with meals, a swimming pool and various massages. It costs about 301US$ per night.

What are the top luxury properties in Chestertown?

Alternatively, you may book Friends Lake Inn with dry cleaning/laundry, concierge service and dry cleaning on site. It costs 523US$ per night.

How much is an average Chestertown hotel price?

According to Booked.net travel data, the average prices for Chestertown properties are:
A 4-star hotel room costs 523US$ per night. You may check The Fern Lodge with snow skiing, a playroom and hiking.
If you're looking for something really special, a 5-star hotel can be found for 301US$ per night. Check Friends Lake Inn with rating 8.8/10.

What's the best hotel for a beach vacation in Chestertown?

For instance, check The Fern Lodge (rating: 8.8/10) offering snow skiing, a playroom and hiking, along with dry cleaning/laundry, concierge service and dry cleaning on site. It costs 523US$ per night.

What are the most popular resorts in Chestertown?

To stay at the top Chestertown resort, check 3 properties on Booked.net. We recommend The Fern Lodge rated 8.8/10 with dry cleaning/laundry, concierge service and dry cleaning on site. It costs about 523US$ per night. Alternatively, check Friends Lake Inn (rating: 8.8/10) for 301US$ per night. It provides meals, a swimming pool and various massages.

Where to stay in Chestertown?

Best cheap hotels in Chestertown

If you're on a budget in Chestertown and want good value for your money, you can stay at the 3-star Sunset Mountain Lodge. You will find Llama House Adk apartment just a stone's throw from Gore Mountain Farms Alpaca.

Convenience of staying in hotels downtown

A convenient accommodation option is Pine Tree Motel & Cabins, which is situated near Loon Lake Beach.

Explore and find your best apartments, B&Bs and others

Guests traveling to Chestertown should consider one of the 3 resorts, such as Sunset Mountain Lodge, which offers free self-parking, a picnic area and a patio with views of the garden.

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