Family Resorts in The Berkshires, 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 Kid Friendly Hotels

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
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

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
$124 nightly
The price is $138 total per night
$138 total
Jan 27 - Jan 28, 2026
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

Stay Berkshires
1146 Cold Spring Road Williamstown MA
Guests of Stay Berkshires enjoy free WiFi in public areas, a seasonal outdoor pool, and a communal living room. Free parking is included with your stay. This smoke-free hotel also has a vending machine.
Pool
Breakfast included

Williamstown Motel
295 Main Street Williamstown MA
Williamstown Motel features free WiFi in public areas, a library, and express check-out. There's free parking if you drive. The front desk has multilingual staff that can help with luggage storage and tours/tickets. Additional amenities include free newspapers, a terrace, and laundry facilities.
Breakfast included
Pet friendly

Cozy Corner Motel
284 Sand Springs Rd. Rte 7 Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
Guests of Cozy Corner Motel enjoy a lazy river, free WiFi in public areas, and a business center. If you drive, take advantage of free parking. Front-desk staff can assist with luggage storage and securing valuables. Other amenities at this family-friendly motel include coffee/tea in a common area, free newspapers, and laundry facilities.
Breakfast included
Parking included

Econo Lodge Lee - Great Barrington
980 Pleasant Street Lee MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
Econo Lodge Lee - Great Barrington features free WiFi in public areas and a vending machine. 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.
Breakfast included
Pet friendly

Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Free Cancellation
Reserve now, pay when you stay
$215 nightly
The price is $241 total per night
$241 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub

Lantern House Motel
256 Stockbridge Road Great Barrington MA
Guests of Lantern House Motel enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This motel also has a garden.
Pool
Breakfast included

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $166 total per night
$166 total
Dec 29 - Dec 30
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, a banquet hall, and an ATM.
Pet friendly
Parking included

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd West Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$52 nightly
The price is $57 total per night
$57 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of Pleasant Valley Motel West Stockbridge enjoy features like free WiFi in public areas. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
Parking included
Free WiFi

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $115 total per night
$115 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Jan 4 - Jan 5, 2026
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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Guests staying at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included

Berkshire Valley Inn
2541 Hancock Rd Williamstown MA
$139 nightly
The price is $155 total per night
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Berkshire Valley Inn, guests have access to free WiFi in public areas, a seasonal outdoor pool, and express check-in. A stay here includes free parking. Front-desk staff can assist with luggage storage and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include express check-out, a banquet hall, and a fireplace in the lobby.
Pool
Breakfast included

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Dec 28 - Dec 29
Total with taxes and fees
Howard Johnson by Wyndham Lenox features an outdoor pool, free WiFi in public areas, and coffee in a common area. There's free parking if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include express check-out, a vending machine, and a garden.
Pool
Parking included
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 | 1,084 hotels |
|---|---|
Lowest Price | $57 |
Highest Price | $241 |
Popular hotels | Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Stay Berkshires, Williamstown Motel, Cozy Corner Motel, Econo Lodge Lee - Great Barrington, Jiminy Peak Mountain Resort, Lantern House Motel, Hotel On North, Pleasant Valley Motel West Stockbridge, Hampton Inn & Suites Berkshires-Lenox, The Yankee, Trademark Collection by Wyndham, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Berkshire Valley Inn, Howard Johnson by Wyndham Lenox |
Recent Kid Friendly Hotels Reviews

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 5 days ago
More to Explore
- Cheap Hotels in Lee
- Business Hotels in Lee
- Kid Friendly Hotels in Lee
- Hotels with Pool in Lee
- Hotels with Balconies in Lee
- Hotels with Bar in Lee
- Hotels with Hot Tubs in Lee
- Hotels with Restaurants in Lee
- Oceanfront Hotels in Lee
- Pet Friendly Hotels in Lee
- Romantic Getaways & Hotels in Lee
- Hotels with Shopping in Lee
- Ski Resorts & in Lee
- Spa Resorts & in Lee
- Hotels with a Wedding Venue in Lee
- 4 Star Hotels in Tyringham
- 5 Star Hotels in Tyringham
- B&B in Tyringham
- Cabin Rentals in Tyringham
- Cottages in Tyringham
- Hotels with Pool in Tyringham
- Lodges in Tyringham
- Rv Parks in Tyringham
- Resorts in Tyringham
- Hotels near Jacob's Pillow
- Hotels near Otis Ridge
- Hotels near Pyramid Lake
- Adventure Hotels in Massachusetts
- Business Hotels in Massachusetts
- Hotels with WiFi in Massachusetts
- Hotels with Air Conditioning in Massachusetts
- Hotels with Balconies in Massachusetts
- Hotels with Childcare in Massachusetts
- Hotels with Free Airport Shuttle in Massachusetts
- Hotels with Free Parking in Massachusetts
- Hotels with Restaurants in Massachusetts
- Hotels with Tennis Courts in Massachusetts
- Hotels on the River in Massachusetts
- 4 Star Hotels in Southfield
- B&B in Southfield
- Inns in Southfield
- Motels in Southfield
- Resorts in Southfield
- Villas in Southfield
- Cottages in New Marlborough
- Cheap Hotels in New Marlborough
- Hotels with Pool in New Marlborough
- Hotels with Bar in New Marlborough
- Pet Friendly Hotels in New Marlborough
- Ski Resorts & in New Marlborough
- Inns in New Marlborough
- Hotels near Ski Butternut
- Apartments in Mill River
- Motels in Mill River
- Town Houses in Mill River
- B&B in Otis
- Cabin Rentals in Otis
- Guest Houses in Otis
- Pet Friendly Hotels in Otis
- Otis Hotels
- Motels in Otis
- Vacation Homes in Otis
- Rv Parks in Otis
- Resorts in Otis
- Golf Resorts & in South Lee
- Hotels with Bar in South Lee
- Hotels with Hot Tubs in South Lee
- Hotels with a Wedding Venue in South Lee
- 3 Star Hotels in Monterey
- Apartments in Monterey
- B&B in Monterey
- Monterey Hotels
- Lodges in Monterey
- Motels in Monterey
- Vacation Homes in Monterey
- Rv Parks in Monterey
- Hotels near Les Trois Emme Winery
- Boutique Hotels in Great Barrington
- Cheap Hotels in Great Barrington
- Luxury Hotels in Great Barrington
- Spa Resorts & in Great Barrington
- Hotels near Ashintully Gardens
- Hotels near Bidwell House Museum
- Hotels near Otis Reservoir
- Adventure Hotels in Lenox
- Hotels near Becket Land Trust Historic Quarry
- Condo Rentals in Sandisfield
- Sandisfield Hotels
- Inns in Sandisfield


