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Accommodations in Chestertown You’ll Love

Affordable, Top-Rated Places to Stay in Chestertown – For Every Budget

Looking for accommodation in Chestertown (Florida)? Discover a wide range of places to stay starting at just $64.00 per night – from hotels and bed & breakfasts to vacation rentals. Whether you're visiting for business or leisure, you'll find the perfect place that fits your budget and travel needs. Book your ideal Chestertown accommodation today!

We found 39 Accommodations in Chestertown and the surrounding area (within 20 miles)

The Lodge at Loon Lake in Chestertown, USA

The Lodge at Loon Lake

Motel in Chestertown, Florida , 5381 State Route 8
Featuring a private beach area, The Lodge at Loon Lake is in Chestertown.
  • Parking
  • Allergy-free room

Superb 92 Reviews 9.3

from $210.89 Show details »

Friends Lake Inn in Chestertown, USA

Friends Lake Inn

Inn in Chestertown, Florida , 963 Friends Lake rd
Located in Chestertown and with Fort William Henry reachable within 26 miles, Friends Lake Inn has concierge services, non-smoking rooms, a garden, fr...
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Kid meals

Very good 47 Reviews 8.0

from $292.32 Show details »

Sagevick Cabin in Chestertown, USA

Sagevick Cabin

Holiday home in Chestertown, Florida
Sagevick Cabin offers accommodations in Chestertown, 26 miles from Fort William Henry and 31 miles from Six Flags Great Escape and Splashwater Kingdom...
  • Parking

no reviews

from $114.71 Show details »

Hunerburg White House in Chestertown, USA

Hunerburg White House

Holiday home in Chestertown, Florida
Hunerburg White House is located in Chestertown, just 31 miles from Six Flags Great Escape and Splashwater Kingdom and 31 miles from Six Flags Great E...
  • Parking

no reviews

from $197.95 Show details »

Basic Adirondack Camp in Chestertown, USA

Basic Adirondack Camp

Holiday home in Chestertown, Florida
Basic Adirondack Camp is located in Chestertown, just 30 miles from Six Flags Great Escape and Splashwater Kingdom and 30 miles from Six Flags Great E...
  • Parking
  • Pets allowed

Fabulous 2 Reviews 9.0

from $228.49 Show details »

Moonbeams & Fireflies in Chestertown, USA

Moonbeams & Fireflies

Holiday home in Chestertown, Florida
Moonbeams & Fireflies offers accommodations in Chestertown, 26 miles from Fort William Henry and 31 miles from Six Flags Great Escape and Splashwater ...
  • Parking

Fabulous 1 Reviews 9.0

from $415.29 Show details »

Pines Way Camp in Chestertown, USA

Pines Way Camp

Holiday home in Chestertown, Florida
Pines Way Camp is located in Chestertown, just 22 miles from Six Flags Great Escape and Splashwater Kingdom and 30 miles from Hudson Falls Historic Di...
  • Parking

Superb 4 Reviews 9.3

from $228.44 Show details »

Private Contemporary in Chestertown, USA

Private Contemporary

Holiday home in Chestertown, Florida
Private Contemporary offers accommodations in Chestertown, 25 miles from Fort William Henry and 29 miles from Six Flags Great Escape and Splashwater K...
  • Parking

no reviews

from $1.027.51 Show details »

Adirondack Mountains Cottage Near Gore Mountain! in Warrensburg, USA

Adirondack Mountains Cottage Near Gore M...

Holiday home in Warrensburg near Chestertown, Florida
Adirondack Mountains Cottage Near Gore Mountain! offers accommodations in Warrensburg, 20 miles from Six Flags Great Escape and Splashwater Kingdom an...
  • Parking

Exceptional 8 Reviews 10.0

from $243.25 Show details »

Whits End in Chestertown, USA

Whits End

Holiday home in Chestertown, Florida
Whits End is located in Chestertown, just 22 miles from Six Flags Great Escape and Splashwater Kingdom and 30 miles from Hudson Falls Historic Distric...
  • Parking

Exceptional 3 Reviews 10.0

from $299.98 Show details »

Hideaway Chalet in Chestertown, USA

Hideaway Chalet

Holiday home in Chestertown, Florida
Hideaway Chalet is located in Chestertown, just 28 miles from Hudson Falls Historic District and 20 miles from Six Flags Great Escape Lodge.
  • Parking

Exceptional 2 Reviews 9.5

from $377.64 Show details »

Hudson Riverside Cottage in Chestertown, USA

Hudson Riverside Cottage

Holiday home in Chestertown, Florida
Free Wifi is available throughout the property and Fort William Henry is 27 miles away.
  • Parking

no reviews

from $257.85 Show details »

Rustic Adirondacks Home with Hot Tub and Lake Access! in Chestertown, USA

Rustic Adirondacks Home with Hot Tub and...

Holiday home in Chestertown, Florida
Rustic Adirondacks Home with Hot Tub and Lake Access! offers accommodations in Chestertown, 31 miles from Six Flags Great Escape and Splashwater Kingd...
  • Parking
  • Pets allowed

Exceptional 4 Reviews 9.8

from $270.05 Show details »

Antler Lake House in North Creek, USA

Antler Lake House

Holiday home in North Creek near Chestertown, Florida
Antler Lake House offers accommodations in North Creek, 27 miles from Six Flags Great Escape and Splashwater Kingdom and 27 miles from Six Flags Great...
  • Parking
  • Pets allowed

Good 3 Reviews 7.0

from $277.13 Show details »

Retreat on the Pond in Chestertown, USA

Retreat on the Pond

Holiday home in Chestertown, Florida
Retreat on the Pond offers accommodations in Chestertown, 26 miles from Six Flags Great Escape and Splashwater Kingdom and 26 miles from Six Flags Gre...
  • Parking
  • Pets allowed

Fabulous 2 Reviews 9.0

from $268.81 Show details »

River Retreat in Brant Lake, USA

River Retreat

Holiday home in Brant Lake near Chestertown, Florida
River Retreat offers accommodations in Brant Lake, 25 miles from Six Flags Great Escape Lodge and 30 miles from Fort Ticonderoga.
  • Pets allowed

no reviews

from $277.95 Show details »

Overlook in Warrensburg, USA

Overlook

Apartment in Warrensburg near Chestertown, Florida
Overlook is located in Warrensburg, just 27 miles from Hudson Falls Historic District and 19 miles from Six Flags Great Escape Lodge.
  • Parking

Good 2 Reviews 7.0

from $145.73 Show details »

Getaway Condo in Warrensburg, USA

Getaway Condo

Apartment in Warrensburg near Chestertown, Florida
Getaway Condo offers accommodations in Warrensburg, 19 miles from Six Flags Great Escape and Splashwater Kingdom and 27 miles from Hudson Falls Histor...
  • Parking

Very good 8 Reviews 8.2

from $145.73 Show details »

Cozy Condo by Tripp Lake in Warrensburg, USA

Cozy Condo by Tripp Lake

Apartment in Warrensburg near Chestertown, Florida
The property is around 20 miles from Six Flags Great Escape and Splashwater Kingdom, 27 miles from Hudson Falls Historic District, and 20 miles from S...
  • Parking

Passable 7 Reviews 5.2

from $98.47 Show details »

Chestertown Hideaway with Lake and Beach Access! in Chestertown, USA

Chestertown Hideaway with Lake and Beach...

Holiday home in Chestertown, Florida
Chestertown Hideaway with Lake and Beach Access! is located in Chestertown, just 30 miles from Six Flags Great Escape and Splashwater Kingdom and 30 m...
  • Parking

Fabulous 4 Reviews 8.8

from $328.24 Show details »

Schroon River Adventures in Warrensburg, USA

Schroon River Adventures

Holiday home in Warrensburg near Chestertown, Florida
Schroon River Adventures is located in Warrensburg, just 25 miles from Six Flags Great Escape and Splashwater Kingdom and 25 miles from Six Flags Grea...
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $307.80 Show details »

Secluded Haven - Guest House in Wevertown, USA

Secluded Haven - Guest House

Holiday home in Wevertown near Chestertown, Florida
Secluded Haven - Guest House offers accommodations in Wevertown, 23 miles from Six Flags Great Escape and Splashwater Kingdom and 23 miles from Six Fl...
  • Parking

Exceptional 1 Reviews 10.0

from $300.09 Show details »

11 Overlook Lane, Unit E in Warrensburg, USA

11 Overlook Lane, Unit E

Apartment in Warrensburg near Chestertown, Florida
11 Overlook Lane, Unit E offers accommodations in Warrensburg, 19 miles from Six Flags Great Escape and Splashwater Kingdom and 27 miles from Hudson F...
  • Parking

Very good 1 Reviews 8.0

from $92.00 Show details »

Secluded Haven - Main House in Wevertown, USA

Secluded Haven - Main House

Holiday home in Wevertown near Chestertown, Florida
Secluded Haven - Main House is located in Wevertown, just 23 miles from Six Flags Great Escape and Splashwater Kingdom and 23 miles from Six Flags Gre...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $317.34 Show details »

Peaceful Brant Lake Home Less Than 1 Mi to Beach! in Brant Lake, USA

Peaceful Brant Lake Home Less Than 1 Mi...

Holiday home in Brant Lake near Chestertown, Florida
Peaceful Brant Lake Home Less Than 1 Mi to Beach! is located in Brant Lake, just 21 miles from Fort William Henry and 25 miles from Six Flags Great Es...
  • Parking

Exceptional 2 Reviews 10.0

from $263.86 Show details »

Number of Accommodations in Chestertown 39
Number of guest ratings 171
Average price per night $316.00
Lowest price per night $64,00
Highest price per night $2.362,60

Top 10 Most Popular Accommodations in Chestertown

Explore the Most Popular Accommodations in Chestertown – Ranked by Average Guest Ratings.

Top 10 Cheapest Accommodations in Chestertown

Discover the Cheapest Accommodations in Chestertown – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Accommodations in Chestertown

Check out the Most Booked Accommodations in Chestertown – Based on Guest Popularity.

Discover Chestertown – Your Guide to the Best Places to Stay

Planning a trip to Chestertown? Choosing the right place to stay is one of the most important parts of making your visit memorable. Whether you are looking for a luxury hotel, a cozy guesthouse, a modern apartment, or a family-friendly vacation rental, Chestertown offers a wide range of lodging options to suit every travel style and budget.

When deciding where to stay in Chestertown, consider key factors like location, amenities, reviews, and proximity to attractions or public transport. Do you prefer being in the heart of the city close to restaurants, shops, and nightlife? Or do you want a quiet neighborhood with a more local feel? With so many types of accommodations in Chestertown, from boutique hotels to spacious homes, you are sure to find something that fits your needs.

Tips for Finding the Perfect Stay in Chestertown

To find the perfect place to stay in Chestertown, consider your budget, preferred location, and the amenities you need. Do you want to stay in a hotel or a vacation rental or do your prefer an apartment or house with more space, privacy, and the opportunity to live like a local? Do you need access to a kitchen, laundry facilities, or a gym? Research online reviews and ratings to get an idea of what past guests have experienced. Also, consider the type of trip you're taking. If you're traveling with family, you may need a larger space or a kid-friendly environment. If you're on a romantic getaway, you may want a more intimate setting.

Accommodation data and pictures provided by Booking.com