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Holiday homes in Chestertown You’ll Love

Top-Rated Chestertown Holiday homes for Every Budget and Style!

Looking for a holiday home in Chestertown (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $64.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chestertown.

We found 30 Holiday-homes in Chestertown and the surrounding area (within 20 miles)

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 »

Family Gem Private Community Beach on Tripp Lake in Chestertown, USA

Family Gem Private Community Beach on Tr...

Holiday home in Chestertown, Florida
Family Gem Private Community Beach on Tripp Lake offers accommodations in Chestertown, 20 miles from Six Flags Great Escape and Splashwater Kingdom an...
  • Parking

Exceptional 1 Reviews 10.0

from $230.81 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 »

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 »

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 »

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 »

Alderbrook Yurt in Warrensburg, USA

Alderbrook Yurt

Holiday home in Warrensburg near Chestertown, Florida , Hendricks Road 193
Alderbrook Yurt offers accommodations in Warrensburg, 16 miles from Fort William Henry and 21 miles from Six Flags Great Escape and Splashwater Kingdo...
  • Parking

no reviews

from $270.00 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 »

Mountain Retreat on Private Lake-Alderbrook Lodge in Bolton, USA

Mountain Retreat on Private Lake-Alderbr...

Holiday home in Bolton near Chestertown, Florida , 275 Hendricks Road
Mountain Retreat on Private Lake-Alderbrook Lodge offers accommodations in Bolton, 16 miles from Fort William Henry and 21 miles from Six Flags Great ...
  • Parking

no reviews

from $1.288.33 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 Road Retreat in Chestertown, USA

River Road Retreat

Holiday home in Chestertown, Florida
The property is around 26 miles from Six Flags Great Escape and Splashwater Kingdom, 26 miles from Six Flags Great Escape Lodge, and 31 miles from For...
  • Parking
  • Pets allowed

no reviews

from $175.62 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 »

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 »

Loon Lake View Newly Built Log Cabin with Fire Pit! in Chestertown, USA

Loon Lake View Newly Built Log Cabin wit...

Holiday home in Chestertown, Florida
Loon Lake View Newly Built Log Cabin with Fire Pit! is located in Chestertown, just 29 miles from Six Flags Great Escape and Splashwater Kingdom and 2...
  • Parking

no reviews

from $86.00 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 »

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 »

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 »

Mossy Bear Retreat in Chestertown, USA

Mossy Bear Retreat

Holiday home in Chestertown, Florida , 23 May Rd
23 miles from Fort William Henry in Chestertown, Mossy Bear Retreat features accommodations with access to a hot tub.
  • Parking

no reviews

from $362.58 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 »

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 »

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 »

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 »

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 »

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 »

Number of Holiday homes in Chestertown 30
Number of guest ratings 171
Average price per night $329.00
Lowest price per night $64,00
Highest price per night $2.362,60

Top 10 Cheapest Holiday-homes in Chestertown

Discover the Cheapest Holiday-homes in Chestertown – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chestertown

Check out the Most Booked Holiday-homes in Chestertown – Based on Guest Popularity.

Holiday homes in Chestertown (Florida), comfortable and familiar

Staying in a holiday or vacation home in Chestertown can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chestertown for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chestertown should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com