The Berkshires Hotels with Pool
Check availability on The Berkshires Hotels with Pool
Featured The Berkshires Hotels with Pool

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
The price is €86 per night
€86
16 Dec - 17 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the free breakfast at The Yankee, Trademark Collection by Wyndham. During your stay, you're just a quick walk from Guido's Marketplace. Features include free WiFi in public areas and free self-parking, plus an indoor pool.
Uima-allas
Poreallas

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is €109 per night
€109
11 Dec - 12 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Vacation Village in the Berkshires. During your stay, you'll be within walking distance of Jiminy Peak Mountain Resort. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool. This comfortable condo has 360 condos over 2 floors. A fireplace and a patio are available in each condo.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is €88 per night
€88
12 Dec - 13 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Holiday Inn & Suites Pittsfield-Berkshires by IHG. During your stay, you're just a quick walk from Berkshire Museum. Features include free WiFi in public areas and free self-parking, plus an indoor pool.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
The price is €122 per night
€122
14 Dec - 15 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. During your stay, you're just a quick walk from Housatonic River. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is €103 per night
€103
20 Dec - 21 Dec
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel's great location gets high marks from our customers. During your stay, you're just a quick walk from MCLA Gallery 51. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.

Berkshire Valley Inn
2541 Hancock Rd Williamstown MA
The price is €116 per night
€116
10 Dec - 11 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Berkshire Valley Inn. During your stay, you'll be close to Jiminy Peak Mountain Resort. Features include free breakfast, free WiFi in public areas and free self-parking. Some of the pet-friendly amenities that this property offers include food and water bowls and an off-lead area.

Club Wyndham Bentley Brook
1 Corey Road Hancock MA
Our customers tell us that they can't get enough of the helpful staff at Club Wyndham Bentley Brook. During your stay, you're just a quick walk from Jiminy Peak Mountain Resort. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.

Berkshire Inn
150 W Housatonic St Pittsfield MA
The price is €83 per night
€83
15 Dec - 16 Dec
includes taxes & fees
Our customers tell us that they enjoy the helpful staff at Berkshire Inn. During your stay, you'll be within walking distance of Berkshire Museum. Free WiFi in public areas, free self-parking and a seasonal outdoor pool are available.

Lantern House Motel
256 Stockbridge Road Great Barrington MA
During your stay at Lantern House Motel, you're just a quick walk from Housatonic River. Features include free breakfast, free WiFi in public areas and free self-parking.

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
The price is €99 per night
€99
21 Dec - 22 Dec
includes taxes & fees
The free breakfast at Hampton Inn & Suites Berkshires-Lenox gets high marks from our customers. During your stay, you'll be within walking distance of Guido's Marketplace. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool. Some of the pet-friendly amenities that this property offers include food and water bowls, an off-lead area and litter trays.

The Porches Inn at Mass MoCA
231 River Street North Adams MA
The price is €157 per night
€157
8 Jan - 9 Jan 2026
includes taxes & fees
The free breakfast at The Porches Inn at Mass MoCA gets high marks from our customers. During your stay, you're just a quick walk from Bracewell Park. Free WiFi in public areas, free self-parking and an outdoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
The price is €76 per night
€76
10 Dec - 11 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Howard Johnson by Wyndham Lenox. During your stay, you're just a quick walk from Guido's Marketplace. Free WiFi in public areas, free self-parking and an outdoor pool are available.

Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
The price is €98 per night
€98
15 Dec - 16 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Holiday Inn Express Hotel & Suites Great Barrington by IHG. During your stay, you're just a quick walk from Housatonic River. Free breakfast, free WiFi in public areas and free self-parking are available.

Stay Berkshires
1146 Cold Spring Road Williamstown MA
During your stay at Stay Berkshires, you're just a quick walk from Margaret Lindley Park. Features include free breakfast, free WiFi in public areas and free self-parking.

Maple Terrace Motel
555 Main St. Williamstown MA
The price is €95 per night
€95
16 Dec - 17 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Maple Terrace Motel. During your stay, you're just a quick walk from Lower Linear Park. Free breakfast, free WiFi in public areas and free self-parking are available. This property offers pet-friendly amenities, such as food and water bowls.
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.
The Berkshires hotels essential information
Accommodation | 1,085 hotels |
|---|---|
Lowest Price | €76 |
Highest Price | €157 |
Popular hotels | The Yankee, Trademark Collection by Wyndham, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Berkshire Valley Inn, Club Wyndham Bentley Brook, Berkshire Inn, Lantern House Motel, Hampton Inn & Suites Berkshires-Lenox, The Porches Inn at Mass MoCA, Howard Johnson by Wyndham Lenox, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Stay Berkshires, Maple Terrace Motel |
More Hotels with Pool
Other accommodation options
Areas of The Berkshires
Hotels by...
Hotels by star rating
Explore Destinations
Top Trending
Hotels
- Hotels near Xfinity Center
- Hotels with Babysitting Services in Hawaii Island
- Cheap Hotels in Hahajima Island
- Scandic Plaza Borås
- Cheap Hotels in Hyvinkaa
- Hotels near Stockholm Archipelago
- Break Sokos Hotel Bomba
- Hotels with Room Service in Jersey Shore
- Cheap Hotels in Lakeland - Winter Haven
- Hotels near Humanitas San Pio X
- Scandic Oulu Station
- Sandies Baobab Beach Zanzibar
- WeHost Kapteeni Sundmanin katu 3
- Hostels Nijmegen
- Hotels with Babysitting Services in Kauai
- Cheap Hotels in Northern Virginia
- Cheap Hotels in Aleutian Islands
- Cheap Hotels in Carcassonne
- Hilton London Metropole
- Hotels near Cushing Academy
- Cheap Hotels in Dubai
Flights
