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Our top choices for Chester holiday rentals
1. Berkshire Mountain Lodge
Berkshire Mountain Lodge3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,273 reviews)
9.0/10
Wonderful
(1,273 reviews)
"Excellent stay!!!!"
"Excellent stay!!!!"
Susan J
The price is ₹7,234
₹7,234
₹10,186 total
includes taxes & fees
6 Dec - 7 Dec
2. Modern Studio Ideal for Traveling Professionals
Modern Studio Ideal for Traveling Professionals3.0 star property
Holyoke
The price is ₹8,105
₹8,105
₹21,932 total
includes taxes & fees
19 Nov - 20 Nov
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.
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.
Find holiday rentals that suit your style
Top Chester Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
10/10 Excellent
A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you
A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you
rose
The Ellery
The ElleryNorthampton
10/10 Excellent
Clean, lovely staff and breakfast
Clean, lovely staff and breakfast
MICHAEL
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
10/10 Excellent
Good breakfast, quiet. Friendly staff. Will definitely stay again!
Good breakfast, quiet. Friendly staff. Will definitely stay again!
Chris
Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
8/10 Good
Laundrette being free really useful. Coffee in main lobby superb quality. Only a few minutes from Market 32 for good food and provisions. A couple of downsides - check-in staff were not particularly friendly and there is a high deposit. Rooms are suites so loads of space.
Laundrette being free really useful. Coffee in main lobby superb quality. Only a few minutes from Market 32 for good food and provisions. A couple of downsides - check-in staff were not particularly friendly and there is a high deposit. Rooms are suites so loads of space.
James
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8/10 Good
All good
All good
Vipada
Monument Mountain Motel
Monument Mountain MotelGreat Barrington
10/10 Excellent
Being a motel I was worried over what the room would be like. After seeing the room I can say this was one of the best motels I have ever stayed in.
The room was clean and a nice size. The bathroom was very large and clean.
I would definitely recommend this motel
Being a motel I was worried over what the room would be like. After seeing the room I can say this was one of the best motels I have ever stayed in.
The room was clean and a nice size. The bathroom was very large and clean.
I would definitely recommend this motel
Allen
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
10/10 Excellent
Helpful staff, clean room and great facilities.
Helpful staff, clean room and great facilities.
Laura
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the BerkshiresSouth Lee
10/10 Excellent
We absolutely loved it here 10/10
We absolutely loved it here 10/10
Judith
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
Excellent room. All very clean.
Excellent room. All very clean.
Martin
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
10/10 Excellent
The hotel was typical 'off the peg' but was very comfortable and offered great facilities. The room was a good size, with everything you would need for a good nights stay. The all you can eat breakfast offered good value, together with 24hr lobby hot drinks was a welcome service after a long drive.
The hotel was typical 'off the peg' but was very comfortable and offered great facilities. The room was a good size, with everything you would need for a good nights stay. The all you can eat breakfast offered good value, together with 24hr lobby hot drinks was a welcome service after a long drive.
Rob
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
10/10 Excellent
The hotel’s reception staff were exceptionally welcoming and helpful.
The hotel’s reception staff were exceptionally welcoming and helpful.
Emma
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
8/10 Good
The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.
The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.
Anonymous traveller
Blue A Modern Hotel, an Ascend Collection Hotel
Blue A Modern Hotel, an Ascend Collection HotelWest Springfield
8/10 Good
Its a lovely hotel and but let down by the rules that rooms are only serviced every 4 days in spite of requests Michael in the management team more than made up for it, Room 431 needs new lights and a bathroom that functions better . No mirrors with lights. No where to put tooth brush or soap bar etc in show. No trays at all . It's not thought through,. It has the makings of a good place and Michael was kind and helpful . We also had great help with rescue from the snow as our car was snowed in....
Its a lovely hotel and but let down by the rules that rooms are only serviced every 4 days in spite of requests Michael in the management team more than made up for it, Room 431 needs new lights and a bathroom that functions better . No mirrors with lights. No where to put tooth brush or soap bar etc in show. No trays at all . It's not thought through,. It has the makings of a good place and Michael was kind and helpful . We also had great help with rescue from the snow as our car was snowed in....
Vivienne
The Inn at Stockbridge
The Inn at StockbridgeStockbridge
10/10 Excellent
Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area.
Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area.
Michele
Find out more about Chester
Holiday Rentals in Chester
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Frequently Asked Questions
Can I find a holiday rental in Chester?
Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfalls and shopping. Make sure you have time to check out the riverfront and restaurants during your trip.
What can I see and do in Chester?
While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake are a couple of places you'll find in the wider area.
What are holiday rentals like in Chester?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family gatherings.