
Family-friendly holiday rentals in Orange
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Top-rated family-friendly rentals in Orange
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Family-friendly home rentals with a hot tub

Private Apt. on Farm, Hot Tub with views!
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

Secluded Farmhouse Retreat - stunning views
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

The Farmhouse - Hot tub eclectic farmhouse 3 br
This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.

Stunning Rustic Apple Barn - hot tub & sauna
We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.

Peaceful cabin close to skiing & Brattleboro
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

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.

Vermont Getaway Apartment
The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!
Family- and pet-friendly home rentals

Cottage
A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.

Apartment on Main Street
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

Private Hilltop farm apartment
What a lovely and serene spot to spend a few days in the Mountains of Vermont! Loved waking up to views of horses in the field by the private deck and a breathtaking mountain view. The hosts were kind and communicative. The space was clean and had just the right amount of amenities. Definitely recommend and hope to stay again!

The Carriage Barn
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Apple Blossom Cottage: A Tiny House
so beautiful and cozy! private and in just the right location.

Rock River Retreat: VT Oasis Pet Friendly
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.

Cottage 7min to Ski Stratton-WoodStove,Views,DogOK
Jason’s place was excellent! Exactly what we were looking for in a country getaway-cozy cabin in the woods, full of charm and close to farms, hiking and swimming. we loved listening to the records while cooking. Perfect spot, perfect vacation!

Private Suite with separate entrance in Worcester
Very roomy and cute place . Love the recliners . Good neighborhood. Friendly , flexible hosts
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

Bear's Den - Mt Snow Townhome w/ Heated Pool!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Hopkinton Mass 3+ Bedrooms - Great location!
Brad was very friendly and helpful. Beautiful home!

Mt Snow Ski In/Out at Seasons
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Cedar Ridge: House or House+Apartment
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again

The Creation Station
John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

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 Orange
Total rentals
20 properties
Nightly prices starting at
₹8,654 before taxes and fees
Total number of reviews
1.3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Manchester Country Club - NH
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- The Shattuck Golf Club
- Ashland State Park
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Douglas State Forest
- Great Brook Farm State Park
- Aaronap Cellars
- Mount Sugarloaf State Reservation
- Hopkinton State Park
- Nashoba Valley Ski Are
- Otis Ridge