Hot Chester Resort Rates

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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 Beartown State ...
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 within a 5-minute walk of Beartown State Forest and Housatonic River.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
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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!
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 Beartown State Forest.
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
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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$154
Highest Price
AU$240
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, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, Mountain Lodge Apt!, Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

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$240 per night from 9 Feb to 10 Feb
AU$240
includes taxes & fees
9 Feb - 10 Feb
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
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$173 per night from 19 Feb to 20 Feb
AU$173
includes taxes & fees
19 Feb - 20 Feb
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
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr, Chicopee, MA
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 12 Feb to 13 Feb
AU$183
includes taxes & fees
12 Feb - 13 Feb
With a stay at Tru by Hilton Chicopee Springfield in Chicopee, you'll be within a 10-minute drive of MassMutual Center and MGM Springfield.
Tru by Hilton Chicopee Springfield
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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$154 per night from 5 Mar to 6 Mar
AU$154
includes taxes & fees
5 Mar - 6 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
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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.

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^Subject to availability and chosen travel dates.