Holiday rentals with a pool in Berkshire County

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

Value · Location · Nearby

Farmhouse Retreat • Hot Tub • Fireplace • Ski

A stylish 4-bedroom farmhouse, thoughtfully designed with modern comfort and historic charm where the Berkshires meet Upstate NY and the Hudson Valley. Surrounded by mature trees, the house offers multiple spaces to gather, with a chef’s kitchen, a den/family/children’s room, outdoor dining, a hot tub, and a generous yard. Minutes to Great Barrington’s dining, lakes, and hiking, and 30 minutes to Tanglewood and Hudson — the Catamount House is an ideal year-round escape for families or friends.

Family · Location · Quiet

Classic New England Home with 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!

Location · Family · Comfort

Top guest favourite

Guest favourite

Private Country Estate | Heated Pool, Sleeps 20

This stunning 7 bedroom, 4.5 bath estate is located on the grounds of a Victorian horse farm, blending elegance, privacy, and comfort. With three wings, there’s room for up to 20 guests. Filled with original art, antiques, and cozy décor, every corner radiates warmth and sophistication. *Heated year-round pool *Brand new game room *Chef’s kitchen w/ Miele, Bosch & SubZero *800sf patio w/ dining & grill *Screened porch w/ meadow views *Brook, meadow & waterfall trail *Tesla charger & fireplace

Location · Family · Skiing

Berkshires Retreat | Fireplace + Hiking + Skiing

Escape to a private 6 bed/3.5 bath family-friendly retreat set on 9 peaceful acres near the Berkshires, Hudson, and Catamount. Spaciously sleeps 12-14, this home is perfect for families & group getaways, and features a private pool, outdoor deck, wood-burning fireplace, renovated kitchen, finished basement with a ping pong table, & multiple gathering areas. Enjoy easy access to hiking, skiing, farm stands, and charming Hudson Valley towns while relaxing in a secluded setting for year-round fun.

Family · Location · Condition

Top guest favourite

Guest favourite

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.

Family · Value · Outdoor spaces

Berkshire Vacation Home in Lee

Our spacious home is situated in a secluded neighborhood in Lee, MA (Berkshire County) and has 5 bedrooms & 2.5 baths. There is a fully equipped open concept kitchen/dining room and 2 living rooms with TVs and gas fireplaces. There is central air/heat, and a sun room that leads out to a deck overlooking our in-ground pool. Tanglewood, Antimony brewery, Balderdash winery, Hilltop Orchards, Laurel Lake, Highlawn Farm, outlets, golf, and Lenox & Stockbridge are all within a 20 minute drive.

Location · Family · Wifi

Top guest favourite

Guest favourite

Stunning luxury home with fire pit

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

Family · Value · Wifi

Chic Eco Studio | Fall Foliage | Sauna

Modern studio tucked into the hillside on over 100 acres. Thoughtfully renovated with sustainability in mind, it blends seamlessly into the landscape. Enjoy a sauna, cool off in the pool, walk up the hilltop enjoy the view. Cool in summer and cozy in winter. Sleep soundly in a Carpe Diem bed dressed with organic cotton sheets. Perfect for a romantic escape or quiet getaway, the studio includes high-speed internet and in-home massage treatments available upon advanced request.

Location · Quiet · Amenities

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Family · Value · Pool

Top guest favourite

Guest favourite

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.

Location · Family · TV

Top guest favourite

Guest favourite

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 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, 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.

Value · Family · Pool