
Family-friendly vacation rentals in Springfield
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Top-rated family-friendly rentals in Springfield
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Popular amenities for Springfield family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Flora @ Norwich Inn & Spa
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

Cozy private apt 8 mins from UCONN - solar powered
The place was quiet, surrounded by beautiful woods, and truly relaxing—it was exactly what I needed. The bed was incredibly comfortable, and I slept so well each night. I also appreciated how responsive the host was to my questions via text. I would love to stay there again in the future. Thank you so much!

Waterfront cottage overhanging the water!
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Secluded Farmhouse Retreat - stunning views
Mark's High Pocket Bed and Barn was absolutely stunning and cozy. My friends and I stayed while attending a wedding nearby, and were so delighted by the home the minute we walked in. Thoughtful furniture and decoration through out the house, as well as beautiful yard and walking paths that were so nice to explore on a sunny spring day. The home was immaculately clean and well stocked. Mark was very communicative and responsive. We would all very happily stay at this home again!

(°) The Wandering Peacock (°)
We only stayed at the Wandering Peacock for 1 night but it was such a treat as a place to crash along our road trip. Not a corner of the home was glossed over, every inch of the place is beautifully curated. Abigail was super responsive and a welcoming host. We squeezed in some time for the hot tub, it was ready to go in 2-3 hours and super relaxing. 10/10 would recommend.

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
We really enjoyed staying here, only wish we booked it for longer! Our son and our dog enjoyed going for walks on the trails behind the brewery. The beers and pizza from the brewery were excellent, the house is really charming and relaxing. Also got out to enjoy the disc golf course which was a fun way to spend the afternoon. I would love to come back and try out the mountain bike trails. The surrounding area was fun to explore, really can't think of any negative points to this place!

Peaceful Spa Escape minutes to Mohegan Sun Casino
Stay was great, enjoyed the Spa and the hot tub ! I wish the hot tub closing times were posted somewhere but other than that it was great ! Fire place was a also very cool and the fire starter that is supplied was very helpful

Charming farmhouse retreat with post-hike hot-tub
This is our second time renting this house and working with Anna and Victoria. They are wonderful and kind hosts and so easy to work with. The entire home was very clean and spotless. We ABSOLUTELY loved our stay and had the perfect girls weekend. The farmhouse is so unique, vintage and spacious. The bathrooms are a women’s dream with the fun designs, lighting and the fun floor tiles. Although we are from Connecticut, we love visiting the Goshen/Litchfield area to get a change of scenery, visit the local winery’s and vineyards in the area and check out downtown Litchfield for lovely dinners and cocktail hours. The book case collection also intrigued us every morning when we were sipping our coffee and looking out the back porch area. We enjoyed the fact that there were tons of board games which we played at least one every night during our stay. We will definitely be booking our next visit and be back to this gorgeous home!
Family- and pet-friendly home rentals

Dog Friendly Studio
We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!

Stone n' Sky Lodge
Sarah and her place were absolutely wonderful!! There are not enough great things to say about Stone n’ Sky Lodge. Our big group of 9 fell in love with cabin immediately, and Sarah was very responsive and made us feel so at-home. As past umass grads, we were familiar with the area, but the cabin gave us a new place to make memories in western Mass. Thank you so much Sarah, you made our trip unforgettable and we can’t wait to come back!

Zachariah House Main St. Ashfield
Great location for exploring nearby towns like Northampton, Amherst, Shelburn falls. As Laura said, no cell service in this town but their WiFi worked great in the unit and it’s a quite peaceful area to stay. The home feels like a well maintained cabin. It’s rustic and cozy but you might find a spider in the shower. I did not find the beds very comfortable but otherwise had a very relaxing stay. Laura was a great host and very responsive

Sunny Berkshire Studio Apartment
Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

Swiss Chalet Style Timberframe Home in Berkshires
I had a wonderful stay at Laura’s place. The home is not only beautiful but thoughtfully constructed. Its exposed wood frame feels so natural and adds to the calming atmosphere. The backyard was clean, maintained, and offered a serene space to relax. Laura’s instructions were clear and made finding and settling into the house easy. The bedrooms and bathrooms were incredibly cozy and well-kept. Every detail made the space feel warm and welcoming. It’s also a fantastic spot for groups. Our group of six friends fit very comfortably, with plenty of space to relax and unwind. I’d absolutely recommend this home to anyone looking for a peaceful, comfortable getaway.

Calm & Cozy House in a Quiet Corner
A nice stay for a family gathering in the area. It worked well for us.

Cozy, Quiet Cottage on Country rd 2 mil from I-91
Stayed here with my 2 pups. Beautiful location, feels so remote, but not far from any sort of restaurant, hiking, or other outing. Highly recommend Lucy's Sweet Shop. Marshall's Country store has a great selection of items. Homemade ice cream is close by, honestly, a great location for a get away, and a very comfortable house. Sitting out on the porch at night and listening to the birds was a favorite activity.

North Street Nest, sunny downtown apartment
Susan accommodated me on short notice when I needed to make a last minute trip. Her place is beautiful and thoughtfully appointed, nothing is neglected. The location is both convenient and peaceful. I can’t wait to stay here again!
Family-friendly home rentals with a pool

Casino Wine Down House
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Escape to a Restored New England Antique Milk Barn
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Cedar Ridge: House or House+Apartment
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!

Affordable In-Law Apartment in Brooklyn, CT
We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.

8 Bedroom, 4 full bath residence with 40' pool
The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!

Light-bathed 3br w porch in best downtown location
My family had a wonderful stay at Susan’s place! It was very clean, well stocked, spacious, and accurately described. My toddlers especially loved playing with the toy trains. There was also a welcome bottle of wine with cheese and crackers which was so thoughtful. The location was great and only a short walk to town. We were visiting for a college reunion and will definitely look to stay here on future trips.
Quick stats about vacation rentals that are family-friendly in Springfield
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
3.3K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
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- Six Flags New England
- TPC River Highlands
- Jiminy Peak Mountain Resort
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
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- Brimfield State Forest
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Douglas State Forest
- Bigelow Hollow State Park
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- Hartford Golf Club
- Hancock Shaker Village
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- Naumkeag
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