Book 4 Star Hotels in Cheshire

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Oct 4 - Oct 5
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Featured Cheshire 4 Stars Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
6.49 mi from city center
$98 nightly
The price is $110 total per night
$110 total
Oct 5 - Oct 6
Total with taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with concierge services and access to locker space. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
9.16 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
9.8 mi from city center
$145 nightly
The price is $161 total per night
$161 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of Hotel Downstreet, an Ascend Collection Hotel have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include a hot tub, express check-out, and laundry facilities.
Pool
Hot Tub
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
10.41 mi from city center
$212 nightly
The price is $236 total per night
$236 total
Nov 2 - Nov 3
Total with taxes and fees
At The Williams Inn, guests have access to a gym, free WiFi in public areas, and a conference center. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include coffee/tea in a common area, a terrace, and a banquet hall.
Pet friendly
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
11.54 mi from city center
$113 nightly
The price is $126 total per night
$126 total
Nov 2 - Nov 3
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
13.38 mi from city center
$88 nightly
The price is $98 total per night
$98 total
Nov 2 - Nov 3
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a fireplace in the lobby, and a water dispenser.
Pet friendly
Parking included
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Free Cancellation
Reserve now, pay when you stay
17.32 mi from city center
$106 nightly
The price is $119 total per night
$119 total
Nov 2 - Nov 3
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$129 nightly
The price is $144 total per night
$144 total
Nov 2 - Nov 3
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Air conditioning
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
20.76 mi from city center
$209 nightly
The price is $233 total per night
$233 total
Nov 4 - Nov 5
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
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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.

Find 4 star hotels in Cheshire

A good hotel meets your expectations, but a great hotel exceeds them. A true 4 star hotel definition includes things like big, comfy beds, stylish décor and friendly service. At Orbitz, we understand that your choice in hotel can make or break an experience, and we are here to help you find the best 4 star hotels for your time in Cheshire. 

What's the difference between a 4 and 5 star hotel?
The difference comes down to level of luxury. While 4 star hotels offer excellent service and quality products, most 5 star hotels will feature complimentary services that go above and beyond, like gourmet dining, luxury spa experiences and poolside service. With 4 star hotels, you’ll find the most comfort without splurging on extras you may not need.

What should I look for in a 4 star hotel?
Cheshire 4 star hotels are likely to include things like:

  • Pool and fitness center
  • Valet parking
  • Room service
  • Dedicated concierge
  • Pillow top mattresses
  • Minibar
  • Bathrobes and bath products
  • Artwork

How do I find the best 4 star hotel?
Orbitz makes finding the best 4 star hotel in Cheshire simple:

  • Pick your price: You’ll find room rates ranging from $98 to $236
  • Get the best quality: 4 star hotels in Cheshire have an average rating of 0.0
  • Read the reviews: Read through reviews to help you choose the hotel that has everything you want

Cheshire hotels essential information

Accommodation
1,007 hotels
Lowest Price
$98
Highest Price
$236
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold, The Red Lion Inn, The Williams Inn, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hotel Downstreet, an Ascend Collection Hotel, Holiday Inn & Suites Pittsfield-Berkshires by IHG

Recent Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

5/5 Excellent
"Great!"
A verified traveler stayed at Vacation Village in the Berkshires
Posted 3 days ago
Vacation Village in the Berkshires

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