Holiday rentals with a pool in Berkshire County

Classic New England Home, Direct trail access

Classic New England Home with DIRECT trail acess – 4BR in Richmond Enjoy the charm of the Berkshires in this spacious 4-bedroom, 2.5-bath home in peaceful Richmond. Perfect for families or remote work, the home features fast Wi-Fi, fully equipped kitchen and 7 acres of natural privacy. Enjoy direct access to spectecular hiking trails, unwind on the patios, restaurants, and historic sites. Minutes from Tanglewood, Kripalu, Lenox and West Stockbridge. Book your stay and make yourself at home!

The Catamount Ski Haus with Pool & Hot Tub

Welcome to the Berkshires! Located almost across the street from the Catamount Ski Resort - come unwind with some fun, peace and adventure. This 4 bedroom 4 bath sits on a 5 acre property nestled amongst the trees with a private pool, hot tub and Mountain View ’s to gaze at. Dine at the quaint, hip restaurant in little cat lodge next to the ski resort, have coffee in Hillsdale at Cook& Larder. Or check out the shops in Great Barrington. There is a ton to do in the Berkshires all year long!

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

The Summerwood Hideout | Mins to Downtown! • Pool

Book your getaway today to Long Pond Luxe in the Berkshires! This recently renovated home features a 3bd / 3 bath main house and a charming pool house for the inlaws or the teenagers that want their own space. Relax by the pool tucked into the full patio, perfect for entertaining in a private woodsy setting just outside Downtown Great Barrington. Whether it's outdoor adventures or relaxing getaways, this peaceful spot has everything you could ask for in a fun, memorable Berkshires escape!

"The Cabin" - Cozy & Rustic Home (Averill Park)

This luxurious log cabin, nestled on 200+ acres of private, expansive wilderness, is the perfect escape. Enjoy sunrise from the front porch, grill on the back deck and explore the 18-hole disc golf course, tranquil Japanese garden, croquet court, swimming pool and multiple walking trails throughout the forest property. Jiminy Peak Ski Resort, the Berkshires, and Saratoga Springs are all nearby. All amenities are provided with a personal touch that will make your stay relaxed and memorable.

Grand Berkshire Manor By Evergreen Home

Evergreen Home Vacation Rentals invites you to The Manor, a refined five-bedroom, 4.5-bathroom retreat in the heart of the Berkshires. This elegantly appointed estate offers the perfect blend of serenity and style, featuring a private pool and spacious living areas for your group. Enjoy effortless access to Tanglewood, Mass MoCA, and premier ski resorts. Whether you’re here for acclaimed dining or mountain adventures, this is your ultimate Berkshire escape. Book your luxury stay today!

Berkshire Mountain House

Bring the whole family to this beautiful home in the woods, just minutes from Mt Greylock hiking, Jiminy Peak skiing, local farms and activities. There's truly something for everyone. Go for pumpkin picking and hayrides at Whitney's Farm or walk/bike Ashuwillticook Rail Trail. We are 10 minutes to Pittsfield and 15 minutes to Williamstown. Or have a great time never even leaving the house, while grilling outside, watching movies in the home theater, or cooking in a chef's kitchen.

Modern Log Cabin w/Pool & Views By Evergreen Home

Evergreen Home Vacation Rentals invites you to this refined log cabin featuring a heated saltwater pool, hot tub, and mountain views. Just 15 minutes to Butternut, this 3-bedroom (5 bed), 3.5-bath escape boasts a stone fireplace, screened porch, and spacious suites. Outside, enjoy the fire pit, lush gardens, and pool house. Perfectly located near West Stockbridge, Lenox, and Great Barrington, this retreat offers rustic charm with modern luxury. Your private Berkshire getaway awaits!

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Berkshire Bliss: Nature + Luxe

Spacious 5-bedroom, 4.5-bath country home combining classic charm, bespoke design with modern comfort. Nestled just 5 minutes from downtown Great Barrington’s shops, restaurants, and galleries, and close to Tanglewood, Ski Butternut, and Catamount. Enjoy a private pool, tennis court, gazebo, and stunning mountain views. Perfect for families or groups seeking a peaceful four-season retreat with easy access to hiking, culture, music, and outdoor adventures.