Chestertown Vacation Rentals

Compare 69 available properties from 15 providers
Chestertown

Compare and find a welcoming rental for as little as $74 per night by searching and comparing the 69 properties listed in Chestertown. By comparing these accommodations, HomeToGo highlights the best deals and the most popular vacation homes in Chestertown.

Recommended Vacation Rentals in Chestertown

Rent a vacation accommodation in Chestertown: from $74 per night

House ∙ 2 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $110
VRBO
5.0
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House ∙ 6 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $158
VRBO
4.0
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House ∙ 7 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $176
HomeAway
5.0
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House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $184
VRBO
5.0
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Apartment ∙ 6 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $145
VRBO
4.1
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Apartment ∙ 6 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $71
VRBO
4.6
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House ∙ 6 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $246
VRBO
5.0
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House ∙ 8 guests ∙ 4 bedrooms
Chestertown, Chester, New York, United States
from $240
VRBO
5.0
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House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $246
VRBO
4.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 5 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $166
VRBO
5.0
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Fireplace
Apartment ∙ 4 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $150
VRBO
4.7
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Fireplace
House ∙ 7 guests ∙ 4 bedrooms
Chestertown, Chester, New York, United States
from $185
VRBO
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $133
VRBO
4.0
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Fishing
Apartment ∙ 5 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $93
VRBO
4.4
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Fishing
Apartment ∙ 6 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $133
VRBO
4.9
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 5 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $961
VRBO
4.7
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Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $203
VRBO
5.0
View deal
Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $263
VRBO
4.9
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Popular Rental Amenities in Chestertown

  • Internet (64)
  • TV (64)
  • No smoking (64)
  • Parking (63)
  • Kitchen (63)
  • Grill (60)
  • Microwave (59)
  • No pets (47)
  • Fishing (47)
  • Fireplace (44)
  • Washer (43)
  • Dishwasher (42)
Accommodations can be chosen based on various criteria. Above, you can see the number of rentals that include a specific amenity in Chestertown. In Chestertown, 43 rentals include "internet". So, if you need internet access during your vacation, select the internet filter to compare these accommodations. Plan your vacation in advance if you're dreaming of days spent poolside or you love sweating the stress away in saunas. There are just 3 listed rentals including "pools" and 6 properties including "saunas."

The Weather in Chestertown

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12°
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43°
21°
57°
34°
72°
46°
77°
54°
82°
59°
81°
57°
73°
48°
61°
39°
48°
28°
37°
23°
Jan.
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June
July
Aug.
Sep.
Oct.
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Dec.
- Rainy days

You can see our climate diagram above. During July, maximum temperatures go up to more than 82° On the contrary, the coolest month is January. The rainiest month is July while the driest month is August.

Accommodations in Chestertown

In Chestertown, two-thirds of the 69 properties are house rentals, which represent 74.42% of its short-term accommodations. Interestingly, specific accommodation type, this type of accommodation in particular is $298 per night, with an average area of 1,910 ft². Moreover, if you are going in a group of 8, house rentals are the perfect property type in Chestertown, as they usually welcome this exact group size. You can also consider other accommodation types in Chestertown. Hotel rooms are, for example, another popular accommodation type in this destination, with 9 currently listed. While house rentals in Chestertown have an average size of 1,910 ft², hotel rooms have an average size of 800 ft².

Get in touch with nature with a vacation home in Chestertown, New York

Not far from the Adirondack Mountain range, Chestertown is the perfect retreat for those wishing to get back to nature. Stunning wilderness, glistening lakes, and a charming local culture are yours to enjoy, in this scenic part of Upstate New York.

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Art & Culture

Chestertown souvenirs

With its eclectic yet thoughtful collection of craft items, Rustic Charm is aptly named. Locally-made jewellery, decorative items, and more make for the perfect souvenirs, while the family-run shop also offers fun arts and crafts workshops.

Before heading off for you wilderness adventure, stop by The Crossroads to pick up some picnic items. Treat the kids to an ice cream - rumored to be the best in the area - and purchase local specialities such as boar meat and gluten-free beer. This is also the best place to buy your fishing equipment.

Family Activities

Family action

For an experience the kids won't forget, take them to Circle B Ranch. Based within Chestertown, the friendly team lead horse rides along excellent trails that take in some superb views. What's more, the horses are well-trained and well-looked-after.

For exciting water sports action, head over to Loon Lake Marina. Kids of all ages can have a go at waterskiing, stand-up paddle boarding, canoeing, and more, as you savor some quality family time.

Local Attractions

Into the wild

Get a taste of the region's natural beauty with a visit to the 1,909-acre Cat and Thomas Mountains Preserve. Taking the yellow trail is highly recommended, due to the breathtaking views of Lake George and the Adirondacks, seen from the summit of Cat Mountain.

Characterised by the rugged cliffs that rise up alongside the Hudson River, the Hudson Gorge Wilderness Area is another top choice for keen hikers. The vast Pharaoh Lake Wilderness Area is also easily reached from your vacation home in Chestertown. With hidden ponds, the giant lake itself, and the 2,551-ft. Pharaoh Mountain, it's a true joy to explore.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Chestertown VRBO Vacation Rentals in Chestertown HomeAway Vacation Rentals in Chestertown TripAdvisor Vacation Rentals in Chestertown VacationRentals.com Vacation Rentals in Chestertown HouseTrip Vacation Rentals in Chestertown FlipKey Vacation Rentals in Chestertown Wimdu Vacation Rentals in Chestertown 9flats.com Vacation Rentals in Chestertown VaycayHero Vacation Rentals in Chestertown PerfectPlaces.com Vacation Rentals in Chestertown Homestay.com Vacation Rentals in Chestertown Only-apartments Vacation Rentals in Chestertown Interhome Vacation Rentals in Chestertown Bedycasa Vacation Rentals in Chestertown Novasol Vacation Rentals in Chestertown HomeEscape Vacation Rentals in Chestertown

Vacation Destinations Near Chestertown