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Accommodations in Chester You’ll Love

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

Looking for accommodation in Chester (Florida)? Discover a wide range of places to stay starting at just $53.00 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 Chester accommodation today!

We found 16 Accommodations in Chester and the surrounding area (within 30 miles)

Holiday Inn Express Hotel & Suites Chester by IHG in Chester, USA

Holiday Inn Express Hotel & Suites Chest...

Hotel in Chester, Florida , 2 Bryle Place
Located off Route 6 in the Hudson Valley, this Chester hotel features an indoor pool and on-site gym.
  • Parking
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Very good 517 Reviews 8.2

from $117.38 Show details »

Fairfield Inn & Suites Goshen Middletown in Goshen, USA

Fairfield Inn & Suites Goshen Middletown

Hotel in Goshen near Chester, Florida , 20 Hatfield Lane
Located near Route 17, this hotel is just a 3-minute drive away from Good Time Park.
  • Parking
  • Fitness centre
  • Family rooms
  • Outdoor pool
  • Swimming pool

Fabulous 261 Reviews 8.7

from $114.51 Show details »

Stagecoach Inn in Goshen, USA

Stagecoach Inn

Hotel in Goshen near Chester, Florida , 268 Main Street
Located in Goshen, 16 miles from Metro-North Harriman Station, Stagecoach Inn provides accommodations with a restaurant, free private parking and a ba...
  • Parking
  • Restaurant
  • Bar
  • Kid meals

Superb 49 Reviews 9.4

from $289.36 Show details »

Sleep Inn & Suites Monroe - Woodbury in Monroe, USA

Sleep Inn & Suites Monroe - Woodbury

Hotel in Monroe near Chester, Florida , 1 Sleep Way
Located in Monroe and with Metro-North Harriman Station reachable within 6.9 miles, Sleep Inn & Suites Monroe - Woodbury has concierge services, non-s...
  • Fitness centre
  • Family rooms
  • Allergy-free room

Fabulous 920 Reviews 8.9

from $90.58 Show details »

LEGOLAND New York Resort in Goshen, USA

LEGOLAND New York Resort

Hotel in Goshen near Chester, Florida , One Legoland Blvd
Located in Goshen, 13 miles from Metro-North Harriman Station, LEGOLAND New York Resort provides accommodations with a seasonal outdoor swimming pool,...
  • Parking
  • Restaurant
  • Bar
  • Fitness centre
  • Family rooms

Good 246 Reviews 7.9

from $252.68 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 »

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 »

Craftsman Hideaway at the 1841 Farmhouse in Chester, USA

Craftsman Hideaway at the 1841 Farmhouse

Apartment in Chester, Florida , 379 Bellvale Road
Craftsman Hideaway at the 1841 Farmhouse is located in Chester, just 24 miles from St Georges Episcopal Church and 25 miles from Michie Stadium.
  • Parking

Superb 5 Reviews 9.2

from $190.58 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 »

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 »

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 »

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 »

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 »

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 »

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 »

Spacious Home with Pool, Hot Tub, Mins to Parks Skiing in Monroe, USA

Spacious Home with Pool, Hot Tub, Mins t...

Apartment in Monroe near Chester, Florida , 214 Berry Road
Spacious Home with Pool, Hot Tub, Mins to Parks Skiing is located in Monroe, just 14 miles from Bear Mountain State Park and 31 miles from The Palisad...
  • Swimming pool
  • Swimming Pool

Exceptional 2 Reviews 10.0

from $459.49 Show details »

Number of Accommodations in Chester 16
Number of guest ratings 531
Average price per night $222.00
Lowest price per night $53,00
Highest price per night $4.122,00

Top 10 Most Popular Accommodations in Chester

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

Top 10 Cheapest Accommodations in Chester

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

Top 10 Most Booked Accommodations in Chester

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

Discover Chester – Your Guide to the Best Places to Stay

Planning a trip to Chester? 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, Chester offers a wide range of lodging options to suit every travel style and budget.

When deciding where to stay in Chester, 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 Chester, from boutique hotels to spacious homes, you are sure to find something that fits your needs.

Tips for Finding the Perfect Stay in Chester

To find the perfect place to stay in Chester, 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