Holiday rentals in Longmeadow

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Lake Views from Hot Tub Fire Pit & 4 Kayaks

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Renovated Pet-Friendly 3BR Near Six Flags & Casino

Welcome to our renovated 3 BR bedroom apartment, thoughtfully designed for a cozy and modern stay. Ideal for families and friends, home-away-from-home atmosphere with spacious bedrooms and a fully equipped kitchen for your convenience. The apartment is located on the second floor and offers added privacy. Enjoy easy access and a prime location close to downtown, casinos, museums, Six Flags, The Big E, and local hospitals. For your convenience, two parking spaces are provided in the driveway.

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Cozy & Spacious Single Family Home

Welcome to a quiet and comfortable home away from home, located just minutes from Forest Park. This spacious property is ideal for families, groups, and professionals looking for a relaxing and convenient stay. Your safety and comfort are a priority! - All surfaces are thoroughly cleaned using CDC-approved disinfectants - All bedding and linens are washed in hot water after every guest - Fresh towels, linens, and pillows are provided for each stay

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Elegant 3BR Longmeadow Home| Sauna| Near Big E

Welcome to your peaceful Longmeadow retreat—perfect for families visiting loved ones, Springfield events, or trips to The Big E. This charming 3BR bungalow features a wood-burning fireplace, outdoor barrel sauna, private backyard, and uplifting artistic touches. Located across from a quiet park and minutes from Springfield, the MassMutual Center, and Eastern States Exposition, it offers a relaxing place to recharge after a busy day.

Hilda’s Riverside Retreat

Amazing Newly renovated Airbnb! Nestled along the meandering, Connecticut River, beautiful veiw! “Just what the doctor ordered”. And just a stone’s throw away from Downtown Springfield, MGM and Hartford. Whether you are visiting the Knowledge Corridor to visit any of the 30+ universities and liberal arts colleges, business or pleasure, This waterfront property is cozy and offers every amenity you left at home!

Linny’s Lake House - with dock

Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!