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 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
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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!
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

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.
Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
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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
6 Resorts
Lowest Price
AU$148
Highest Price
AU$226
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, Mountain Lodge Apt!, Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee

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$222 per night from 27 Apr to 28 Apr
AU$222
includes taxes & fees
27 Apr - 28 Apr
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$226 per night from 20 Apr to 21 Apr
AU$226
includes taxes & fees
20 Apr - 21 Apr
With a stay at Berkshires Untold in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 30 Apr to 1 May
AU$199
includes taxes & fees
30 Apr - 1 May
A stay at La Quinta Inn & Suites by Wyndham Springfield MA places you in the heart of Springfield, within a 5-minute drive of Paramount Theater and MGM ...
La Quinta Inn & Suites by Wyndham Springfield MA
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Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 11 May to 12 May
AU$148
includes taxes & fees
11 May - 12 May
In the heart of West Springfield, Quality Inn West Springfield is within a 5-minute drive of Olympia Ice Center and Big E.
Quality Inn 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.