Photo by Elizabeth Massa Peroulakis

Search Resorts in Chester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 6 Resorts in Chester with updated reviews, rates, and availability.

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Property grounds

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Holiday Inn Club Vacations Oak 'n Spruce Resort
View from property

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Pool

Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

2.0 star property
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Mountain Lodge Apt!
Private kitchen

Mountain Lodge Apt!

Mountain Lodge Apt!
Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
Indoor pool, outdoor pool

Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee

Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
Canyon Ranch Lenox
Exterior

Canyon Ranch Lenox

3.0 star property
Canyon Ranch Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 855 total
includes taxes & fees
7 Apr - 8 Apr
Berkshire Village Carriage House - Super Private!!
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What is Chester like for a resort vacation?
You deserve to get away, and a resort is the ideal place to find all the amenities and services you need for a relaxing stay in Chester. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chester?
Our highest-rated resort near Chester: Holiday Inn Club Vacations Oak ‘n Spruce Resort - Ski resort. 15 mi (24.1 km) from Chester. Enjoy the sauna, fitness center, and terrace.
What can I do in Chester?
Experience the local theater scene at Chester Town Hall, or bring the kids to Ashintully Gardens for some family fun. In the area, other attractions include Glendale Falls and Iroquis Waterfront.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Chester?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.