Hot Chester Resort Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Resorts in Chester

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

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

Pittsfield
Located in Pittsfield, this resort is in a rural location, within a 5-minute drive of Guido's Marketplace and Bousquet Ski Area.
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

2 out of 5
190 Meadow Street, South Lee, MA
With a stay at Holiday Inn Club Vacations Oak 'n Spruce Resort in South Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic ...
Holiday Inn Club Vacations Oak 'n Spruce Resort
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

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

2 out of 5
Lee
With a stay at this resort in South Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Lee
With a stay at this resort in South Lee, you'll be a 3-minute walk from Housatonic River and within a 5-minute drive of Berkshire Theatre Festival.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Mountain Lodge Apt!

Mountain Lodge Apt!

Pittsfield
With a stay at this resort in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Guido's Marketplace.
Mountain Lodge Apt!
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Chester Hotel Resorts

You’ve got it made. From your amazing bae to a job you love, you know you’re truly #blessed. But your fake work rivalry with Jenny in accounting is getting pretty heated, and she just took an amazing trip. No worries. Chester resort accommodation has that little extra something that will give you the edge in the tea room.

Travelling with the clan? You can stay at family resorts on a budget no matter how many ankle biters you’ve got. Let the kids splash in the pool while you stretch out on a chaise lounge like you own the place. You could also just leave the kids at home (and if you don’t have any, well, even better) and just do your own thing with adults-only resorts in Chester. Just do you. Sip on tropical drinks with tiny umbrellas, take delicate bites of hors d’oeuvres (after you #foodstagram them, obvs), and add so much to your social media story, you’ll feel like a celebrity. No one at home has to know you had such a great time in Chester without them.

Humble brag: You’ll find such great deals on lastminute.com.au, you’ll have trouble picking just one—but at these prices, you don’t have to. Cheap holiday resorts in Chester are just the beginning. You’re gonna love this trip so much, you’ll want five more just like it, so you might as well book them all now. Then bust out those new bathers and sunnies that got you looking like Beyoncé. You deserve it.

Chester Resorts essential information

Accommodation
5 Resorts
Lowest Price
AU$149
Highest Price
AU$197
Popular accommodation
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!, Holiday Inn Club Vacations Oak 'n Spruce Resort, Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, Mountain Lodge Apt!

Top trending hotels in Chester

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
The price is AU$197 per night from 16 Mar to 17 Mar
AU$197
includes taxes & fees
16 Mar - 17 Mar
With a stay at D. Hotel Suites & Spa in Holyoke, you'll be 4.6 mi (7.4 km) from Smith College and 10.4 mi (16.7 km) from University of Massachusetts ...
D. Hotel Suites & Spa
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 27 Mar to 28 Mar
AU$153
includes taxes & fees
27 Mar - 28 Mar
When you stay at Red Roof Inn PLUS+ West Springfield in West Springfield, you'll be in the business district, within a 10-minute drive of MassMutual Center and ...
Red Roof Inn PLUS+ West Springfield
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 20 Mar to 21 Mar
AU$171
includes taxes & fees
20 Mar - 21 Mar
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
Save an average of 15% on thousands of hotels when you're signed in
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 23 Mar to 24 Mar
AU$149
includes taxes & fees
23 Mar - 24 Mar
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.