Vacation rentals with a pool in Pioneer Valley

1880s sun-bathed beauty in best downtown location

Sun-drenched, recently renovated 2nd floor apartment in gracious 4-family Victorian home, steps from Northampton's vibrant downtown. Wonderful open living/dining/kitchen space with new stainless-steel appliances, butcher block counters, wood floors, lots of seating & 42" HDTV. Master BR with queen bed, small 2nd BR with double bed, pull-down sofa in living room. Comfy high-end mattresses. New, small-ish bathroom with shower and tiled floor. Washer and dryer in basement (shared with another apt).

*Berkshire's Sweet Spot-Close to ski/Spa open

The Berkshire's Sweet Spot 2 property is an entire half of a duplex apartment located in central Berkshire County within walking distance to downtown. Renting both sides of the home may be an option. They are recently updated for your comfort with newer kitchens, baths and new smart televisions. The location can't be beat for seeing all of the Berkshire's attractions. The neighborhood is very peaceful, quiet and safe. Enjoy your own private oasis with seasonal in ground pool and year round Spa!

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my newly renovated 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 or master bed & enjoy the cozy ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

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.

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Berkshire Lakefront Home W/Pool-100%Renovated

On beautiful Lake Pontoosuc in The Berkshires, you can enjoy this brand new construction complete with pool! This home has been entirely renovated from top to bottom! Every room has a king sized bed! 2 bedrooms are on the main floor complete with en-suite baths. Gorgeous views from every room! Conveniently located near Lenox, Williamstown, North Adams and West Stockbridge. Motorboat lake with rentals available! Kayaks supplied!

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

Unwind above tranquil waters, marinate in the pool, bundle beneath the blanket as the crackling fire radiates warmth, savor freshly roasted coffee perched on the mountain, unify with nature or imbibe libations with friends, this property affords serenity for all. Steps from skiing at Ski Sundown, fishing, hiking, golfing, tubing or boating, you will depart rested, restored and renewed. Hot tub up and running for the winter!

Charming Guest Cottage with Private Pool

Nestled in a narrow valley in Litchfield County, this charming guest cottage is located on a stunning 275 acre estate at the end of a mile long private drive. With its own private pool and spa behind stone walls, it is perfect for couples looking for a romantic retreat. Rural, but not remote, we are a 2+ mile walk to the village of Cornwall, and a 25 minute drive to Litchfield, Kent, Sharon, and Falls Village.