Berkshire County Hotels with Pools

The beautiful Berkshires may remind you of those quintessential Norman Rockwell paintings. But families don’t need to stay “picture-perfect” to have a great time hiking, skiing, rafting or enjoying fall leaves all near the Appalachian Trail. Messy hair and muddy shoes from the great outdoors are the norm here. After a day of exploring, Oak n’ Spruce Resort is the perfect place to kick up your feet and relax. Located in South Lee, near Lenox, MA, Oak n’ Spruce Resort is a family-inspired retreat that features indoor and outdoor pools, an arcade, pool tables, movie theater, 18-hole mini golf course, sports courts and two bars. It’s also at the heart of outdoor fun and cultural attractions. Visit the Norman Rockwell Museum and Tanglewood, the summer home of the Boston Symphony Orchestra. Tap into your adventurous side and go skiing or boating. Take a hike in Mount Greylock State Reservation to reach the highest elevation in the state and fill up your camera roll with brightly colored fall foliage. Or venture out of South Lee and Lenox, MA, and head over to Albany, NY, and Hartford, CT, both about an hour away. Oak n’ Spruce Resort offers spacious one- to three-bedroom villas from 826 to 1,689 square feet. Each comes with extra space in the living room and a full-sized kitchen, along with washers and dryers in select villas. Laundry facilities are also available onsite. Please note there is a resort fee that includes a variety of onsite amenities.

Ideally located for exploring all the Berkshires has to offer, Element Lenox Berkshires offers a refreshing and eco-friendly retreat that blends modern comfort with nature's beauty. Conveniently located to Tanglewood, Jacob’s Pillow, Norman Rockwell Museum, General Dynamics, Berkshire Medical Center and more! Outdoor enthusiasts can enjoy close proximity to Bousquet Mountain, Jiminy Peak, the Appalachian Trail, and Mount Greylock. Designed for both long and short term travelers, this hotel features spacious, pet friendly rooms and suites with kitchenettes, each thoughtfully designed with sustainability in mind. Take a ride with our bikes to borrow or go for a swim in our indoor saltwater pool. Our complimentary breakfast served daily offers a variety of nourishing options to start your day off right. Whether you're here to explore the region’s scenic landscapes, experience its cultural richness, or simply unwind, Element Lenox Berkshires is the perfect place to stay in your element on your next trip.

With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River. This historic hotel is 0.2 mi (0.3 km) from Schantz Galleries and 0.2 mi (0.4 km) from Mission House. Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Grab a bite at Main Dining Room, one of the hotel's 3 restaurants, or stay in and take advantage of the 24-hour room service. Quench your thirst with your favorite drink at the bar/lounge. Full breakfasts are available daily from 7 AM to 10 AM for a fee. Featured amenities include a 24-hour business center, dry cleaning/laundry services, and a 24-hour front desk. Make yourself at home in one of the 125 air-conditioned rooms featuring DVD players. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers. Conveniences include desks and irons/ironing boards, as well as phones with free local calls.

When you stay at Brook Farm Inn in Lenox, you'll be near ski lifts, within a 5-minute drive of Tanglewood Music Center and Shakespeare and Company. This bed & breakfast is 2 mi (3.2 km) from The Mount and 2.1 mi (3.4 km) from Kennedy Park. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this bed & breakfast include complimentary wireless internet access, concierge services, and wedding services. Take advantage of the bed & breakfast's room service (during limited hours). Unwind at the end of the day with a drink at the bar/lounge or the poolside bar. A complimentary cooked-to-order breakfast is served daily from 7:30 AM to 10:00 AM. Featured amenities include express check-in, express check-out, and a library. Event facilities at this bed & breakfast consist of conference space and a meeting room. Free self parking is available onsite. Make yourself at home in one of the 15 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Conveniences include ceiling fans, as well as phones with free local calls.

With a stay at Devonfield Inn B&B in Lee, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Greenock Country Club. This golf bed & breakfast is 1 mi (1.6 km) from Lee Library and 1 mi (1.6 km) from Animagic Museum of Animation. Don't miss out on recreational opportunities including an outdoor pool and bicycles to rent. This bed & breakfast also features complimentary wireless internet access, concierge services, and a hair salon. Meet other guests and eat at the complimentary reception. A complimentary full breakfast is served daily from 8:30 AM to 9:30 AM. Featured amenities include complimentary wired internet access, a business center, and complimentary newspapers in the lobby. Free self parking is available onsite. Make yourself at home in one of the 11 air-conditioned rooms featuring flat-screen televisions. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Bathrooms have jetted bathtubs and complimentary toiletries. Conveniences include complimentary newspapers and separate sitting areas, and housekeeping is provided daily.

With a stay at The Inn at Stockbridge in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Theatre Festival. This bed & breakfast is 1.7 mi (2.7 km) from Housatonic River and 1.8 mi (2.9 km) from Schantz Galleries. Take advantage of recreation opportunities including an outdoor pool and a 24-hour fitness center. This bed & breakfast also features complimentary wireless internet access and a fireplace in the lobby. A complimentary cooked-to-order breakfast is served daily from 8:30 AM to 10 AM. Featured amenities include complimentary wired internet access, multilingual staff, and a library. Free self parking is available onsite. Make yourself at home in one of the 14 air-conditioned rooms featuring flat-screen televisions. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Bathrooms have designer toiletries and hair dryers. Conveniences include ceiling fans and irons/ironing boards, and housekeeping is provided daily.

Fully renovated and decor updated in 2024! 8 acre property, shared with one carriage house not rented, with amazing views of October Mountain and one mile from Lenox Center. 1.5 miles from Tanglewood. The property features so much, pool, chess set, sport court, gardens abound, a wraparound porch you can enjoy a relaxing day. A wonderful place to re-charge and enjoy your time. The property has 5 bedrooms and a separate crib room. It sleeps 10 in beds (without the child in the crib room) - a maximum of 16 are allowed in the house.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

With a stay at The Ponds at Foxhollow in Lenox, you'll be in the entertainment district, within a 10-minute drive of Tanglewood Music Center and The Mount. This condominium resort is 1.9 mi (3.1 km) from Housatonic River and 2.3 mi (3.7 km) from Berkshire Mountain Country Store. Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and a hot tub. Additional features at this condominium resort include complimentary wireless internet access, an arcade/game room, and a picnic area. Featured amenities include a business center, a 24-hour front desk, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 48 air-conditioned rooms featuring fireplaces. Rooms have private balconies or patios. Kitchens are outfitted with refrigerators, ovens, and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

Escape to this superb fully equipped house on our 220 acre lake estate. With 4 bedrooms including 1 queen bed, 3 twin beds, and 1 full bed. Enjoy the convenience of a full bath in every bedroom. Relax in the great room with a sofa bed for additional sleeping space. Private dock with two canoes, 2 kayaks and rowboat. Fabulous 40' deck with hot tub and fire pit. 1500 acre Highlawn farm across the street, Tanglewood 2 miles. Indoor & Outdoor pools, tennis courts, gym and club house on premises. Make your holiday one for the books with a stay at our place.About pets:Pets allowed: dogs (limit 2 total).About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.

The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City. The house has 8 foot ceilings and provide a nice 'vacation' like feel with every bedroom but one having its own bath. The common areas are designed for fun and socializing with family and friends.The 6 fireplaces provide ambiance and a feeling of escape into a time long forgotten. Play a game of pool, chess or checkers with your family. Enjoy two kitchens in which to work from, sit together at the 12 person dining area while enjoy a fire in the large hearth as you drink your wine and soak in the feeling of the Berkshires. This home has it all and it is designed to give you and your group a relaxing and fulfilling vacation.Keywords: The Williams House dates to 1797 and has been completely updated in 2010. This home boasts 6 bedrooms, 5.5 baths, two terraces, 6 fireplaces, two full service cook's kitchens, a billiard room, large family room, dining area and table that seats 12 and a lounge/game area. This is the ultimate vacation rental. The house is situated 2 miles from Stockbridge Center, on 4 acres of pristine land with two patios and large grassy areas for outdoor fun. Enjoy all that the Berkshires offer while staying in luxury with your family and friends.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.