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Holiday homes in Chester You’ll Love

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

Looking for a holiday home in Chester (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 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 Chester.

We found 9 Holiday-homes in Chester and the surrounding area (within 50 miles)

Family Home Close to Warwick, 5 Mi to Lake! in Monroe, USA

Family Home Close to Warwick, 5 Mi to La...

Holiday home in Monroe near Chester, Florida
Family Home Close to Warwick, 5 Mi to Lake! is located in Monroe, just 8.2 miles from Metro-North Harriman Station and 17 miles from Bear Mountain Sta...
  • Parking
  • Spa and wellness centre

Exceptional 1 Reviews 10.0

from $418.58 Show details »

Decked-Out Home Hot Tub, Pool, Fire Pit and More! in Monroe, USA

Decked-Out Home Hot Tub, Pool, Fire Pit...

Holiday home in Monroe near Chester, Florida
Decked-Out Home Hot Tub, Pool, Fire Pit and More! offers accommodations in Monroe, 14 miles from Bear Mountain State Park and 26 miles from The Palisa...
  • Parking
  • Bar
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $56.00 Show details »

Hudson Valley Cottage Rental 3 bedrooms Monroe NY in Monroe, USA

Hudson Valley Cottage Rental 3 bedrooms...

Holiday home in Monroe near Chester, Florida , 137 Berry Road
Featuring a garden, Hudson Valley Cottage Rental 3 bedrooms Monroe NY features accommodations in Monroe.
  • Parking

Fabulous 21 Reviews 9.0

from $283.46 Show details »

1786 Farm Cottage Honeymoon Suite Renovated 2022 in Chester, USA

1786 Farm Cottage Honeymoon Suite Renova...

Holiday home in Chester, Florida , 379 Bellvale Road
1786 Farm Cottage Honeymoon Suite Renovated 2022 is located in Chester, just 21 miles from Bear Mountain State Park and 24 miles from St Georges Episc...
  • Parking

Fabulous 11 Reviews 8.7

from $229.42 Show details »

Relaxing New York Home with Boat Dock and Lake View! in Monroe, USA

Relaxing New York Home with Boat Dock an...

Holiday home in Monroe near Chester, Florida
Relaxing New York Home with Boat Dock and Lake View! is located in Monroe, just 15 miles from Bear Mountain State Park and 21 miles from St Georges Ep...
  • Parking

Good 2 Reviews 7.5

from $385.71 Show details »

Large 5-bedroom home with a pool in Chester, USA

Large 5-bedroom home with a pool

Holiday home in Chester, Florida , 7 Summerville Road
Large 5-bedroom home with a pool offers accommodations in Chester, 14 miles from Metro-North Harriman Station and 20 miles from Bear Mountain State Pa...
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $72.00 Show details »

Secluded Sanctuary in Nature in Monroe, USA

Secluded Sanctuary in Nature

Holiday home in Monroe near Chester, Florida , 1296 New York 208
Secluded Sanctuary in Nature offers accommodations in Monroe, 10 miles from Metro-North Harriman Station and 16 miles from Bear Mountain State Park.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $67.00 Show details »

Very Private Large Home on 22 Acres in Chester, USA

Very Private Large Home on 22 Acres

Holiday home in Chester, Florida , 1 Errins Trail
Very Private Large Home on 22 Acres is located in Chester, just 11 miles from Metro-North Harriman Station and 17 miles from Bear Mountain State Park.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $55.00 Show details »

Goshen House: hot tub, fenced yard, by downtown in Goshen, USA

Goshen House: hot tub, fenced yard, by d...

Holiday home in Goshen near Chester, Florida , 27 Bruen Place
Goshen House: hot tub, fenced yard, by downtown is located in Goshen, just 16 miles from Metro-North Harriman Station and 22 miles from Bear Mountain ...
  • Parking
  • Pets allowed

Fabulous 2 Reviews 9.0

from $361.57 Show details »

Number of Holiday homes in Chester 9
Number of guest ratings 531
Average price per night $310.00
Lowest price per night $53,00
Highest price per night $4.006,36

Top 10 Cheapest Holiday-homes in Chester

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

Top 10 Most Booked Holiday-homes in Chester

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

Holiday homes in Chester (Florida), comfortable and familiar

Staying in a holiday or vacation home in Chester 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 Chester 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 Chester 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