Book 5 Star Hotels in The Berkshires
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured The Berkshires 5 Stars Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
28.42 mi from city center
$120 nightly
The price is $134 total per night
$134 total
Aug 4 - Aug 5
Total includes 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 access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
36.81 mi from city center
$170 nightly
The price is $190 total per night
$190 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of Hotel Downstreet, Ascend Hotel Collection 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 a vending machine.
Pool
Hot Tub
The Williams Inn
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
37.59 mi from city center
$251 nightly
The price is $280 total per night
$280 total
Aug 11 - Aug 12
Total includes 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, concierge services, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, a terrace, and a picnic area.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
20.16 mi from city center
$129 nightly
The price is $144 total per night
$144 total
Jul 27 - Jul 28
Total includes 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 dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
20.23 mi from city center
$127 nightly
The price is $141 total per night
$141 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
21.05 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
9.73 mi from city center
$172 nightly
The price is $192 total per night
$192 total
Jul 30 - Jul 31
Total includes 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
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.41 mi from city center
$199 nightly
The price is $222 total per night
$222 total
Jul 27 - Jul 28
Total includes 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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
17.41 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
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 The Berkshires
Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in The Berkshires. 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 The Berkshires 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?
The Berkshires 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 The Berkshires 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 $88 to $280
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 1,114 5 star hotels in The Berkshires!
The Berkshires hotels essential information
Accommodation | 1,114 hotels |
|---|---|
Lowest Price | $88 |
Highest Price | $280 |
Popular hotels | Vacation Village in the Berkshires, Hotel Downstreet, Ascend Hotel Collection, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, FairBridge Inn Express, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold, The Yankee, Trademark Collection by Wyndham |
Recent Reviews
The Williams Inn
5/5 Excellent
"We did not care for the barn door to the bathroom. Wouldn't stay closed and large gap meant a loud radio or TV required... Otherwise, our stay was great and we would definitely recommend it."
A verified traveler stayed at The Williams Inn
Posted 3 days ago
Areas Of The Berkshires
Hotels Near
Hotel Themes
Flights To
Book on Expedia
Top Trending
Hotels
- Romantic Getaways & Hotels in Cape Cod
- Luxury Hotels in Central Massachusetts
- Pet Friendly Hotels in Cape Cod
- Hotels with Hot Tubs in North Shore
- Hotels in Martha's Vineyard
- Oceanfront Hotels in Cape Cod
- Kid Friendly Hotels in Cape Cod
- Hotels with an Indoor Pool in Cape Cod
- Hotels with Balconies in Cape Cod
- Hotels in Nantucket Island
- Beach Resorts & Hotels in Cape Cod
- All Inclusive Resorts & Hotels in Cape Cod
- Spa Resorts & Hotels in Cape Cod
- Romantic Getaways & Hotels in Western Massachusetts
- Hotels in Cape Cod
- Cheap Hotels in Cape Cod
- Hotels with Hot Tubs in Cape Cod
- Hotels with Hot Tubs in Western Massachusetts
- Casino Resorts & Hotels in Cape Cod
- Hotels with Kitchenettes in Cape Cod
- Waterpark Hotels & Resorts in Cape Cod
Flights