Family-friendly holiday rentals in Springfield

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.

Lake Views from Hot Tub Propane 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

Serene 1-br suite on 75 acre horse property

Escape to a peaceful 1-bedroom suite on a beautiful 75-acre horse property. Tucked into the woods 1/3 mile from the main road, enjoy privacy, scenic nature trails, and views of up to 20 horses grazing in the pastures outside your windows. Relax in the guest gazebo with front-row views of the horses, perfect for morning coffee or unwinding outdoors. Enjoy a private entrance, dedicated workspace, and high-speed WiFi. Conveniently near Amherst, UMass, Smith, and Mount Holyoke Colleges.

4 BR Entire House w/Hot Tub

This home is nestled in a family neighborhood, on a quiet road that ends with a cul-de-sac. This is a whole house rental, not a shared space. Situated about one mile from the Connecticut line, there is quick access to Rte. 91. Bradley International Airport is a 15 minute ride in light traffic. The Basketball Hall of Fame, MGM Casino, Dr. Seuss Museum, Six Flags, The Big E, Springfield Symphony Orchestra, just a few of the area attractions. Great restaurants and grocery shopping nearby.

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat. Per-person pricing. Please select the correct number of guests when booking.

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.

Cozy Brick House in Chicopee

Relax with the whole family at this peaceful place to stay. The unit is part of a two family duplex house. You and your family will have the entire unit to yourselves. There are two bedrooms with queen size beds, a living room, kitchen, bathroom, and laundry room. The living room has a TV, fireplace, and Netflix. There is also a fenced in back yard with a patio and outdoor dining area as well as a firepit. The house is also pet-friendly.

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

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.

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Thompson stay or extended stay retreat

Newly remodeled 2nd floor space. Centrally located to major highways, downtown Springfield with the newly opened MGM casino. It's a fantastic spot in the city! Large master bedroom, second bedroom, full kitchen, claw foot bath tub, washer and dryer included. Secure parking. Extended stay is welcomed. No more than 4 people, including children. Additional fee will be charged.