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$150
Highest Price
AU$220
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$220 per night from 4 May to 5 May
AU$220
includes taxes & fees
4 May - 5 May
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
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
The price is AU$201 per night from 21 May to 22 May
AU$201
includes taxes & fees
21 May - 22 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
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$179 per night from 4 May to 5 May
AU$179
includes taxes & fees
4 May - 5 May
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
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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$150 per night from 18 May to 19 May
AU$150
includes taxes & fees
18 May - 19 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.