
Family-friendly holiday rentals in Springfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Springfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Luxury studio apartment-walkout basement
Located in a quiet neighbor hood in Sixteen acres springfield, this luxury studio was created with you in mind! The bathroom is loaded with spa like amenities include a rain head shower, and heated floors. Located 7 minutes from Western New England University, 13 minutes from Springfield College and American International College. Also conveniently close to many restaurants and shopping amenities. The perfect stay for a traveling nurse or a business trip or even as the home base for a getaway!

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Separate apt, 1 mile from downtown, 1 guest only
This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Cozy studio loft
Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Brookside Carriage House. Private, Great Location.
1890's Carriage House. Bright 850 sq. ft., 2nd flr. studio. Original wood flrs, 12' ceiling, skylights, modern amenities w/ rustic charm. Onsite parking. Two sleeping nooks: One QUEEN, One FULL bed & a leather couch; open floor plan. Shower, laundry, full kitchen, dining table, lounging area, Juliet balconey. Eclectic, spacious, private, quiet, all in a fantastic location. This is a large studio. Staircase to 2nd floor. No TV. Dog friendly; contact me first. Non-Smoking/vaping.

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.

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.

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!
Popular amenities for Springfield family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy private apt 8 mins from UCONN - solar powered

Sweet suite, walk to town tout suite!

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

The Creation Station

Hadley Hay House | No Cleaning fees!

Cozy Cottage |Quintessential CT | Pet Friendly

Riverfront Getaway

Peaceful Snowy Lake Views from Private Hot Tub
Family- and pet-friendly home rentals

Trainmaster's Inn - Caboose

Staying at Ten Hillcrest

Water Forest Retreat -Octagon

Tiny House Farm Retreat: Mountain Views, Fire pit

Light filled three bedroom apartment DT Florence!

Bright Noho studio suite perfect walk to downtown

Private Cozy Suite, 0 Fees, Pets Allowed, EV Plug

The cozy clubhouse
Family-friendly home rentals with a pool

The Vacay Villa

Peaceful Oasis steps from Mohegan Sun

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Enjoy every season the Berkshires have to offer.

59 Old Maids Lane pool house

Mountaintop Horse Farm with Pool

1880s bright sun+design in best downtown location

Sunlit Clean Amherst Cozy Log Cabin
When is the best time to visit Springfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $221 SGD | $218 SGD | $222 SGD | $221 SGD | $229 SGD | $229 SGD | $216 SGD | $227 SGD | $240 SGD | $240 SGD | $242 SGD | $224 SGD |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about holiday rentals that are family-friendly in Springfield

Total holiday rentals
Explore 100 holiday rentals in Springfield

Nightly prices starting at
Springfield holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 3,870 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
100 of Springfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Springfield rentals

4.7 Average rating
Springfield stays receive an average rating of 4.7 out of 5 from guests
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Mohegan Sun
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Mount Southington Ski Area
- Taconic State Park
- Powder Ridge Mountain Park & Resort
- Norman Rockwell Museum
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- Naumkeag
- Hancock Shaker Village
- Clark University
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- Connecticut Science Center
- Dcu Center
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