Book 5 Star Hotels in Stockbridge

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Nov 25 - Nov 26
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Featured Stockbridge 5 Stars Hotels

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
0.57 mi from city center
$184 nightly
The price is $206 total per night
$206 total
Dec 21 - Dec 22
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 concierge services, securing valuables, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
1.29 mi from city center
$414 nightly
The price is $462 total per night
$462 total
Dec 8 - Dec 9
Total with taxes and fees
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included
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
2.58 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Nov 30 - Dec 1
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 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
3.87 mi from city center
$106 nightly
The price is $119 total per night
$119 total
Dec 15 - Dec 16
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
7.22 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Nov 30 - Dec 1
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 water dispenser, and a fireplace in the lobby.
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
9.09 mi from city center
$99 nightly
The price is $110 total per night
$110 total
Dec 7 - Dec 8
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
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
6.96 mi from city center
$84 nightly
The price is $94 total per night
$94 total
Dec 8 - Dec 9
Total with taxes and fees
Guests of Quality Inn enjoy a gym, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a microwave in a common area, free newspapers, and a water dispenser.
Breakfast included
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
11.57 mi from city center
$89 nightly
The price is $100 total per night
$100 total
Nov 29 - Nov 30
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 securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
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
19.22 mi from city center
$94 nightly
The price is $105 total per night
$105 total
Nov 29 - Nov 30
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
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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.

Best 5 star hotels in Stockbridge

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Stockbridge. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Stockbridge hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Stockbridge 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Stockbridge with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $94 to $462
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 1,347 5 star hotels in Stockbridge!

Stockbridge hotels essential information

Accommodation
1,347 hotels
Lowest Price
$94
Highest Price
$462
Popular hotels
The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Quality Inn

Recent Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

5/5 Excellent
"Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. Gas fireplace worked well, hot water was plentiful, water pressure was good. Kitchen was stocked with just about anything you'd need to cook simple meals. Great option when in the area, would recommend and would stay again."
A verified traveler stayed at Vacation Village in the Berkshires
Posted 3 days ago
Vacation Village in the Berkshires

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