Holiday rentals with a pool in Hampshire County

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in 4-family Victorian on tree-lined street in downtown Northampton. Easy walk to Smith campus. Skylights; large tiled bathroom w/ shower, jacuzzi tub, washer/dryer; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, lg TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony. Home theatre in master bedroom. Off-street parking.

High Field Farm

Come to High Field Farm to getaway and unwind in a beautiful, classic New England farmhouse. Set on over 500 acres of land, enjoy a spacious, tasteful and pristine country vacation home, lovingly cared for by the same family for over 50 years. The house offers four bedrooms and two full bathrooms, and endless outdoor opportunities like hiking or fly-fishing. You'll enjoy spectacular mountain views in an idyllic and private country setting that will enchant and nourish your heart and soul.

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

Newly Constructed Guest House with Pool

200 sf guest house adjacent to our home. Space complete w/ wifi, heat, A/C + ceiling fan. QUEEN size sleeper sofa , full size mattress in sleeping loft, kitchenette w/sink + mini fridge, HALF bath, OUTDOOR shower, private patio and in-ground pool. Outdoor lighting allows for nighttime enjoyment of guest house, pool and enclosed yard. Walking distance to Florence ctr, 2 mi from downtown Northampton. THIS SPACE IS MORE COMFORTABLE FOR 2 PEOPLE - but there is enough sleeping space for 3.

Serene South Deerfield Retreat

Discover a quiet escape in the heart of historic South Deerfield, MA. This thoughtfully renovated home blends rustic charm with modern comforts, creating a warm and welcoming space for adult families, couples, or professionals looking to unwind, explore and recharge. Located at the base of Mt Sugarloaf and minutes from Yankee Candle, Treehouse Brewery, Deerfield Academy and the Connecticut River. This cozy retreat offers easy access to some of Western MA most beloved attractions.

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.

Stay in Robert Frost's beautiful house

From 1931 to 1938, Robert Frost lived in this gracious 1874 house, located on a quiet, lovely Amherst street a short walk from town, Amherst College, and UMass. The house can be yours for a country getaway, family get-together, or reunion/graduation weekend. High-ceilinged, private, full of remarkable details, and surrounded by beautiful old trees, this is a piece of Amherst history that is ready for your convivial group.

Nestled Inn

Situated on a seldomly travelled side road, in a quiet neighborhood with views of fields and mountains, your nest awaits. Three miles or less to Historic Deerfield, Yankee Candle, Magic Wings butterfly conservatory and gardens. 100 miles to Boston.

Happy Valley getaway

Private, peaceful location nestled conveniently between Northampton and Easthampton. Great for Five college visits or getting to any Western, MA location. Minutes to restaurants, colleges and Mount Tom. Pool is closed Labor Day through Memorial Day.