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Chestertown (NY) hotels and places to stay

Search among 28 available hotels and places to stay in Chestertown from 50+ providers.

When you reserve Chestertown accommodation with Booked.net, you will find heaps of affordable options. Our website has search filters which you may find very useful while looking for 5-star hotels and places to stay in Chestertown near tourist attractions. We have business and spa hotels with a large list of facilities and services along with other attractive accommodation options which provide you with an ideal base for exploring.Hide
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  • Price: low to high
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  • Popularity: high to low
Bed & Breakfast
  • The bed & breakfast has
    • Free Wi-Fi in rooms
  • The bed & breakfast has
    • Bar/ Lounge area
    • Outdoor dining area
  • The bed & breakfast has
    • Fitness centre
View on map3.1 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.
9.0
Perfect15 reviews
From   US$ 522 /nightSelect
Not available
  • The inn has
    • Bar/ Lounge area
    • Restaurant
View on map2.6 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$ 274 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
3.2 mi from City Center
Rustic Charm is 6 km from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 407 /nightSelect
Not available
11 adults
6 bedrooms
6 beds
100 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$ 659 /nightSelect
Not available
5 adults
2 bedrooms
4 beds
2.4 mi from City Center1.1 mi from Ridin Hy Ranch Resort
Offering a kitchen equipped with a microwave, a dishwasher and a fridge, this villa is set near Rustic Charm.
From   US$ 215 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
3.6 mi from City Center
Gore Mountain Farms Alpaca is 10 km from this villa that offers 3 bedrooms along with a kitchen.
From   US$ 232 /nightSelect
Not available
2.2 mi from City Center2.2 mi from City Center
The hotel offers a budget accommodation with 8 rooms in the beach area of Chestertown.
From   US$ 141 /nightSelect
Not available
6 adults
4 bedrooms
4 beds
4.0 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$ 260 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
2.2 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$ 207 /nightSelect
Not available
23 adults
5.8 mi from City Center
Set 10 km from Rustic Charm, this property features a picnic area and barbeque grills.
From   US$ 99 /nightSelect
Not available
7 adults
4 bedrooms
6 beds
3.3 mi from City Center
Rustic Charm is 3.4 miles from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 195 /nightSelect
Not available
7 adults
4 bedrooms
4 beds
2.9 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$ 798 /nightSelect
Not available
4 adults
2 bedrooms
2 beds
5.6 mi from City Center
This is a 1-bedroom villa, set in proximity to Natural Stone Bridge and Caves.
From   US$ 235 /nightSelect
Not available
8 adults
3 bedrooms
3 beds
3.5 mi from City Center
Prospect Mountain is 30 km from this villa that offers 3 bedrooms along with a fully-fitted kitchen.
From   US$ 281 /nightSelect
Not available
1.6 mi from City Center1.6 mi from City Center
A few meters away you can enjoy Rustic Charm.
10.0
Perfect1 review
Select
Not available
6 adults
3 bedrooms
3 beds
3.4 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$ 372 /nightSelect
Not available
Villa
8 adults
4 bedrooms
4 beds
2.8 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$ 571 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
2.5 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$ 315 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
2.9 mi from City Center2.9 mi from City Center
This vacation home is a 10-minute drive from Dynamite Hill Recreation Area and offers hiking and fisheries.
From   US$ 573 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
3.6 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$ 362 /nightSelect
Not available
2 adults
1 bedroom
2 beds
3.7 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
14 adults
4 bedrooms
4 beds
3.6 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$ 489 /nightSelect
Not available
6 adults
3 bedrooms
4 beds
5.6 mi from City Center
This is a 3-bedroom villa, set in proximity to Natural Stone Bridge and Caves.
From   US$ 171 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
3.5 mi from City Center
Rustic Charm is 6 km from this villa that offers 3 bedrooms along with a full kitchen.
From   US$ 294 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
2.3 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$ 363 /nightSelect
Not available
12 adults
2.6 mi from City Center2.6 mi from City Center
Situated in vicinity of Circle B Ranch, the well-equipped villa entices guests with canoeing and fishing.
Select
Not available
10 adults
5 bedrooms
7 beds
3.7 mi from City Center
Situated a 20-minute drive to Rustic Charm, this villa features the balcony and a patio.
From   US$ 622 /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$ 480 /nightSelect
Not available

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28 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 5-star hotels in Chestertown?

The best one is Friends Lake Inn rated 8.8/10 at the cost of 274US$ per night with a golf course, concierge service and canoeing. See more 5-star options here.

Which hotels for couples in Chestertown are the best to stay at?

According to Booked.net travel data, there are 4 deals for couples. The Fern Lodge rated 9.0/10 is a favorite 4-star hotel for couples, featuring a gym, canoeing and hiking. Travelers can book a room at this property for about 522US$ per night. Other suitable options for couples you can find here.

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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