Alquileres vacacionales con piscina en Pittsfield

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

The Oliver Wendell Holmes Guesthouse @ Holmesdale

Built in 1847 by Oliver Wendell Holmes Sr., this two-story historic cottage on the 16-acre “Holmesdale” estate in the Berkshires features original wood floors, fireplace, high-end appliances, AC/heat, and seasonal pool/tennis access 9am-9pm. Near Pittsfield/Lenox border, close to Tanglewood, dining, skiing, and fall foliage. Guests must provide names of additional guests staying for safety purposes. We aim for a five-star experience while ensuring competitive affordability with area lux hotels

Pool, Farmhouse, Pets Welcome at Roundhill Farm

An historic 1750 farmhouse on a quiet, beautiful 120 acre property. Huge rooms with wide plank original flooring, 6 bedrooms, large family room with fireplace, kitchen, dining room, and formal living room. The property includes a pond which you're welcome to skate on in the winter, and a horse barn and pastures. In the summer you'll have access to our in-ground pool. We welcome your pets! Come ski Jiminy Peak, only a 25-minute drive from this airbnb! The house sleeps 11 people comfortably.

Townhouse w/ King Bed, Kitchen, Tub, Patio, Office

Enjoy our newly furnished and remodeled, spacious Townhouse with a private entrance and king bed! Located in a quiet and safe location in the up-and-coming town of Clifton Park (Saratoga County). 25 minutes to Saratoga National Historical Park. 10 min drive from shopping, entertainment & dining. 18 minutes to Saratoga Race Course, Saratoga Performing Arts Center, and Saratoga National Golf Club. Just a short drive to downtown Albany & surrounding Troy, Schenectady, Ballston Spa and Latham.

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

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!

Grand Berkshire Manor By Evergreen Home

Welcome to The Manor – your refined escape to the tranquil beauty of the Berkshires. Discover a perfectly situated, spacious retreat in the heart of the region. This elegantly appointed five-bedroom / 4.5 bathroom home offers serenity, comfort, and style — complete with a private pool, peaceful surroundings, and effortless access to iconic destinations like Tanglewood, Mass MoCA, The Norman Rockwell Museum, premier ski resorts, and acclaimed dining experiences.

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.