Book 5 Star Hotels in The Berkshires

Name: Hotel Downstreet, an Ascend Collection Hotel
Price range: $120 total

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Dec 4 - Dec 5

Tonight

Dec 5 - Dec 6

Tomorrow night

Featured The Berkshires 5 Stars Hotels

Free Cancellation

Reserve now, pay when you stay

28.42 mi from city center

$101 nightly

$113 total

Dec 7 - Dec 8

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 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

Free Cancellation

Reserve now, pay when you stay

17.93 mi from city center

$101 nightly

$113 total

Jan 4 - Jan 5, 2026

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

Free Cancellation

Reserve now, pay when you stay

37.59 mi from city center

$186 nightly

$208 total

Dec 9 - Dec 10

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, luggage storage, and concierge services. Additional amenities include coffee/tea in a common area, a terrace, and a ballroom.

Pet friendly

Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Free Cancellation

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20.16 mi from city center

$93 nightly

$104 total

Dec 5 - Dec 6

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

Free Cancellation

Reserve now, pay when you stay

16.41 mi from city center

$114 nightly

$127 total

Dec 7 - Dec 8

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

Free Cancellation

Reserve now, pay when you stay

11.5 mi from city center

$169 nightly

$189 total

Jan 4 - Jan 5, 2026

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, luggage storage, 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

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

Free Cancellation

9.73 mi from city center

$122 nightly

$136 total

Dec 8 - Dec 9

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 Yankee, Trademark Collection by Wyndham

Free Cancellation

Reserve now, pay when you stay

17.41 mi from city center

$62 nightly

$70 total

Dec 14 - Dec 15

Total with 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 concierge services, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.

Pool

Hot Tub

Hotel Downstreet, an Ascend Collection Hotel

Free Cancellation

36.81 mi from city center

$107 nightly

$120 total

Dec 20 - Dec 21

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 securing valuables and luggage storage. Additional amenities include a hot tub, express check-out, and laundry facilities.

Pool

Hot Tub

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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 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 $70 to $208
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Choose from 1,088 5 star hotels in The Berkshires!

The Berkshires hotels essential information

Accommodation	1,088 hotels
Lowest Price	$70
Highest Price	$208
Popular hotels	Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Hotel Downstreet, an Ascend Collection Hotel