The Berkshires hotels

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Booking Insights
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Latest The Berkshires Hotel Deals

MOST POPULARStockbridge
3 stars from 159 €
4+ stars from 333 €
Lee
3+ stars from 78 €
Lenox
3 stars from 90 €
4+ stars from 218 €

Best The Berkshires hotels

These are the best prices for 24-25 Oct.
The Red Lion Inn - Stockbridge - Lounge
The Red Lion Inn
Stockbridge, MA, United States
8.1Very Good(654)
Parking
Free Wi-Fi
Pool
Pet-friendly
412 €+
Check availability
Stockbridge Country Inn - Stockbridge - Business centre
Stockbridge Country Inn
Stockbridge, MA, United States
9.3Wonderful(65)
Parking
Free Wi-Fi
Pool
Air Conditioning
523 €+
Check availability
The Cottage - Stockbridge
The Cottage
Stockbridge, MA, United States
5.8Fair(139)
Parking
Free Wi-Fi
Pet-friendly
Air Conditioning
250 €+
Check availability
Cozy Stockbridge Cabin - Walk to Beach and Lake! - Stockbridge - Living room
Cozy Stockbridge Cabin - Walk to Beach and Lake!
Stockbridge, MA, United States
9.3Wonderful(20)
Cabin
Parking
Free Wi-Fi
Air Conditioning
238 €+
Check availability
Stockbridge Home: Walk To Town Beach - Stockbridge - Living room
Stockbridge Home: Walk To Town Beach
Stockbridge, MA, United States
9.6Wonderful(17)
House
Parking
Free Wi-Fi
Air Conditioning
334 €+
Check availability
Tranquil 3 BR Stockbridge House w/ Private Deck! - Stockbridge
Tranquil 3 BR Stockbridge House w/ Private Deck!
Stockbridge, MA, United States
10Wonderful(19)
House
Parking
Free Wi-Fi
Pet-friendly
Air Conditioning
349 €+
Check availability
The Inn at Stockbridge - Stockbridge - Gym
The Inn at Stockbridge
Stockbridge, MA, United States
9.7Wonderful(116)
Parking
Free Wi-Fi
Pool
Pet-friendly
486 €+
Check availability
Secluded Family Home in Serene Stockbridge Woods - Stockbridge - Dining room
Secluded Family Home in Serene Stockbridge Woods
Stockbridge, MA, United States
10Wonderful(12)
House
Free Wi-Fi
Air Conditioning
549 €+
Check availability
A Charming Mid 1800's Stockbridge Farmhouse. - Stockbridge - Building
A Charming Mid 1800's Stockbridge Farmhouse.
Stockbridge, MA, United States
10Wonderful(19)
House
Free Wi-Fi
Air Conditioning
364 €+
Check availability
Completely Renovated Historic Home in the Heart of the Berkshires - Stockbridge - Living room
Completely Renovated Historic Home in the Heart of the Berkshires
Stockbridge, MA, United States
10Wonderful(5)
House
Air Conditioning
417 €+
Check availability
Conroy's B&B - Stockbridge
Conroy's B&B
Stockbridge, MA, United States
8.7Very Good(17)
Air Conditioning
51 €+
Check availability
Seasons on Main Bed and Breakfast - Stockbridge
Seasons on Main Bed and Breakfast
Stockbridge, MA, United States
9.9Wonderful(9)
Free Wi-Fi
74 €+
Check availability
Booking Insights

KAYAK’s insights for hotels in The Berkshires

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in The Berkshires with confidence.

How much is a hotel in The Berkshires for this weekend?

The cheapest hotel room in The Berkshires for the upcoming weekend found on KAYAK in the last 3 days was for 269 € per night. For the same dates, 3-star hotel rooms have been found for as low as 269 € per night and 4-star hotel rooms from 368 € per night.

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How much is a The Berkshires hotel?

Here are our most popular & best value hotels

Good to know

Average price (weeknight)

275 €

Average price (weekend night)

402 €
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a hotel in The Berkshires

  • What is the most popular destination in The Berkshires?

    Based on KAYAK hotel searches, the most popular destination is Drury (50% of total searches to The Berkshires). The next most popular destination is Stockbridge (50%).

  • How much is a cheap hotel in The Berkshires?

    KAYAK users have found double rooms in The Berkshires for as cheap as 246 € (Stockbridge) in the last 3 days. The average price is 246 €.

Where to stay in The Berkshires?

Our map will help you find the perfect place to stay in The Berkshires by showing you the exact location of each hotel.

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