
Mga matutuluyang bakasyunang may pool sa Berkshire County
Maghanap at mag‑book ng mga natatanging matutuluyang may pool sa Airbnb
Mga nangungunang matutuluyang may pool sa Berkshire County
Sumasang‑ayon ang mga bisita: may mataas na rating ang mga matutuluyang may pool na ito dahil sa lokasyon, kalinisan, at marami pang iba.

Summer Berkshires Estate | Pool, Sleeps 20
PRIME SUMMER DATES AVAILABLE at our 7 bedroom, 4.5 bath estate 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 *Chef’s kitchen w/ Miele, Bosch & SubZero *800 sf patio w/ dining & grill *Screened porch w/ meadow views *Brook, meadow & waterfall trail *Tesla charger & fireplace

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.

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!

"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, croquet court, swimming pool (June-September)and multiple walking trails throughout the forested 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.

Stunning luxury home with pool
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!

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.

Berkshire Lake House, gunite pool, Chef's Kitchen
This newly updated Berkshire lake house with private in-ground pool, is the perfect place for a year-round vacation. Nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. 5 light-filled bedrooms can accommodate a family retreat or 3 families. Enjoy the pool table, chefs kitchen, two living room areas, and wood burning fireplace inside and fire pit outside. All bedrooms and common areas have air conditioning.

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.

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.

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.

Sweet Dreams Retreat
Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.
Mga patok na amenidad para sa mga matutuluyang may pool sa Berkshire County
Mga matutuluyang bahay na may pool

Pool & Hot Tub Escape • Hudson Valley-Berkshires

The Summerwood Hideout | Mins to Downtown! • Pool

Classic New England Home with a Swimming Pool

Berkshire Mountain House

Mountainside Condo w/ Private Access To Ski Slope

Berkshire Lakefront Home W/Pool-100%Renovated

Berkshires Colonial Farmhouse

Family Lodge at Jiminy Peak - Pools & Adventure
Mga matutuluyang condo na may pool

Berkshires Vacation Village

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

THE SLOPE slope-view Country Inn 1BR w/heated pool

Jiminy Peak Apartment

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

Jiminy Peak Country Inn - ski in/out condo MT view

Vacation Village in Berkshires 12/28/25-1/4/26
Iba pang matutuluyang bakasyunan na may pool

Mountainside Condo Ski on/off

Historic Stockbridge Villa on 25 acres sleeps 16

Ski-InSki-Out Loft Lift&MT.Views

The Nest at Birdland

$5,500/mo Special * Private Berkshire Escape*

LuNo - Relaxing Ski and Culture Berkshires Escape

Jiminy Peak Slopeside Getaway • Ski & Adventure

Newly Renovated Mountainside Townhome, Jiminy Peak
Mga destinasyong puwedeng i‑explore
- Mga matutuluyang guesthouse Berkshire County
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- Mga matutuluyang may pool Massachusetts
- Mga matutuluyang may pool Estados Unidos
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area at Tubing Center
- Hunyo Farms
- Taconic State Park
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Lugar ng Ski ng Mohawk Mountain
- Ski Sundown
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Naumkeag
- Unibersidad ng Massachusetts Amherst
- Museo ng Norman Rockwell
- MVP Arena
- New York State Museum
- Smith College
- Poets' Walk Park
- Mga puwedeng gawin Berkshire County
- Mga puwedeng gawin Massachusetts
- Sining at kultura Massachusetts
- Pamamasyal Massachusetts
- Pagkain at inumin Massachusetts
- Libangan Massachusetts
- Mga Tour Massachusetts
- Kalikasan at outdoors Massachusetts
- Mga aktibidad para sa sports Massachusetts
- Mga puwedeng gawin Estados Unidos
- Pamamasyal Estados Unidos
- Mga Tour Estados Unidos
- Pagkain at inumin Estados Unidos
- Libangan Estados Unidos
- Sining at kultura Estados Unidos
- Mga aktibidad para sa sports Estados Unidos
- Wellness Estados Unidos
- Kalikasan at outdoors Estados Unidos





