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

Riverfront Getaway
Second time staying here, and we continue to love it! The location is great: pretty much anything in western Mass can be reached within about an hour or less from the house. At the house itself, you have a clean, comfortable, and ample space. The hot tub overlooking the river is definitely a highlight. The sounds of the river and the occasional rumble of trains passing by create a beautiful atmosphere. Highly recommended!

Cozy private apt 8 mins from UCONN - solar powered
We have been staying here over the last 4 years, when we visit UConn, and will miss it now that our daughter has graduated. Keri is wonderful host, welcoming & accommodating. Her home in the woods is a refuge, comfortable, peaceful, and minutes from campus.

Home in historic Litchfield village
Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.

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!

A Magical Spot on Little Robin Lake
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.

Large secluded house in the Woods; Pool, hot tub!
We came as a group of friends with a baby to stay at Blake and Tracy's house, and we had a great stay. They were very communicative and accommodated all our requests to ensure our stay was excellent. They asked in advance if it would be okay for their child to stay in his room inside the house, and we agreed. We didn’t see him at all during our stay, and it didn’t disturb us in the slightest. The fact that Blake and Tracy live right next door was convenient, as they were readily available for anything we needed, but we never felt their presence. We will definitely come back!

Amazing Berkshire Mountains Cabin
David & Nicki's cabin in the Berkshires was perfect for our three couple for a weekend of golfing the Berkshires. It was easy to check in and very clean upon arrival. Everything was as described, and we enjoyed our stay. We would return to this home for future trips.
Family- and pet-friendly home rentals

Light-filled Studio Apt. Near Smith
A great stay! The space was exactly as described and Carol and Robin were terrific hosts. East checkin and out and we loved the tea, milk and yogurt + homemade granola! It was very comfortable and cozy, surrounded by loads of books.

Stone n' Sky Lodge
We needed a place for our family - 3 couples and 2 young children - to stay for the wedding of our daughter. Sarah's house was great. It had plenty of room for the kids to play inside as it rained a good part of our visit. (Fortunately the rain held off for the wedding.) Sarah provided eggs fresh from her chickens - they were delicious. She also gave us information about local restaurants. We saw wild turkeys walking outside the house. All in all a delightful stay.

Zachariah House Main St. Ashfield
This is a lovely cottage in a lovely town. The farmer’s market on Saturday morning is right across the street. We strolled around town taking in the splendor of the scenery. Quiet and cozy, the cottage is well stocked with a lived-in feel. The beds were comfortable.

19th c. Barn in The Berkshires
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Flamig Farm Staycation
I was apprehensive about not staying in a hotel but this turned out perfect! Saved money not only on the space but also on food as we had access to a full kitchen and a grill. Being able to run a load of laundry meant less we had to pack and less to do when we came back home. All the staff at the farm was friendly, knowledgeable and welcoming. This was such a different experience for our family. The kids loved being about to feed and pet the animals on the farm, and even got to collect chicken eggs! They enjoyed having more space than they would have in a hotel and reading the books and playing the games available. The binders of local things to do/places to eat were so nice to have and everything was labeled well with instructions, such as the grill and dishwasher. We felt at home and secluded at the farm yet still able to do all the tourist things. We visited both Boston and NYC which are both about 2½hr drive. Also drove up the Six Flags New England. 10/10 would recommend!

South Quarter House
Great Atmosphere

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.

Private Guest House Downtown Noho
Good location on the edge of downtown without being loud at all. Very walkable and parking was easy to find on nearby streets. The rail trail was nearby as well as lots of neighborhoods to be able to walk the dog, great pet friendly spot.
Family-friendly home rentals with a pool

Sunny Inspirit Apartment in best downtown location
very nice place! we slept very well! comfortable, quiet, relaxing! we would stay there again!

Nestled Inn
Great stay, had everything we needed. Host was very accommodating!

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Luxury Home * Pool * Fireplace
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

Light-bathed 3br w porch in best downtown location
Great location, excellent space for 6!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Beautiful 2BD Villa in Berkshires Resort
If you come to the Berkshires, this is a clean, comfortable, spacious place for two couples, with nice resort amenities. The kitchen is minimally equipped, but adequate for preparing simple meals.

1880s sun-bathed beauty in best downtown location
I got a great last minute deal on this place and am so so happy I stayed here! Fantastic location and truly such a lovely space. Felt right at home when I found our welcome gift of a bottle of wine, some cheese and crackers upon arrival! Thank you for having us Susan, we loved your home!
Quick stats about holiday rentals that are family-friendly in Holyoke
Total rentals
40 properties
Nightly prices starting at
$89 SGD before taxes and fees
Total number of reviews
2.6K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Six Flags New England
- TPC River Highlands
- Bushnell Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Brownstone Adventure Sports Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Brimfield State Forest
- Norman Rockwell Museum
- Beartown State Forest
- Douglas State Forest
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Bigelow Hollow State Park
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Naumkeag