Family-friendly holiday rentals in Randolph

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Randolph family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars1 month ago
Nice place thanks Mike
Guest favourite
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars3 weeks ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
Guest favourite
Cabin in Starksboro
4.88 out of 5 average rating, 281 reviews

Charming getaway tucked away in the Green Mtns

SarahRating, 5 stars1 month ago
We appreciated how pet friendly this place was! Fenced in yard. Blankets to cover the furniture to allow dogs on them. Close enough to many different ski mountains. Perfect to come home to the wood stove and hot tub.
Guest favourite
Chalet in Ludlow
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars4 weeks ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Guest favourite
Home in Stowe
4.94 out of 5 average rating, 189 reviews

Huge deck, hot tub, foosball, surrounded by nature

MaritaRating, 5 stars4 weeks ago
Great stay at Jen’s beautiful chalet. Easy to communicate with and well equipped with many kitchen supplies and all the needed towels, linens, hairdryers, and a thoughtful welcome package. Only about 15 mins from the mountain and 10 mins to town. Thanks!
Guest favourite
Home in Warren
4.9 out of 5 average rating, 103 reviews

4br, 3ba with 2 master bedrooms, Sauna, Hot Tub

PaulRating, 5 stars1 month ago
Sugarbush Ski House Our stay at this besutiful Airbnb ski house in Sugarbush, Vermont, was nothing short of spectacular. From the moment we arrived, we were impressed by the spacious, modern design and the thoughtful details that made this home a great place for a family trip. The house has nice open floor plan with great views both from in the house and a large deck on the outside. The living room was very comfortable with space for all including two dogs. The kitchen is modern and has great appliances, supplies, and prep area. The bedrooms were large with comfortable beds and modern bathrooms. The other amenities were top-notch. The sauna and hot tub were absolute luxuries after a long day on the slopes, providing the ultimate relaxation experience. Everything was impeccably clean and well-maintained, adding to the overall comfort and ease of our stay. If you’re planning a trip to Sugarbush, this house is not to be missed. Definitely a five star house!!
Guest favourite
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars1 month ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend
Guest favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars1 month ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.

Family- and pet-friendly home rentals

Top guest favourite
Cabin in Corinth
4.99 out of 5 average rating, 240 reviews

Skip's Place

ClaireRating, 5 stars1 month ago
This is an ideal spot for a winter getaway, and Matt goes above and beyond to provide guests with the best possible experience. During the day, we enjoyed snowshoeing and sledding on the property. At night, the stars truly amazed us. We also enjoyed the cozy fire in the wood stove…a very nice thing for the cold temps we were having. The house is well stocked and beds are comfortable. We are so grateful for the few days we spent recharging at Skip’s Place.
Guest favourite
Home in Bristol
4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

ChristopherRating, 5 stars2 months ago
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.
Guest favourite
Flat in Hinesburg
4.91 out of 5 average rating, 268 reviews

Backyard Bunker Retreat

TaylorRating, 5 stars1 week ago
The place was everything we expected and more! Lynn was super nice and helpful, we informed her that we were running early and she let us check in to the Airbnb 40 minutes early. We loved having all that space to explore with the dogs. It truly was the perfect place for our weekend getaway. I would love to come back in the fall!
Superhost
Home in Moretown
4.92 out of 5 average rating, 139 reviews

South Hill Lodge- 5 BR Post & Beam Home

JenniferRating, 5 stars2 months ago
Beautiful home, as described. Nice personal touches with towels and mini shampoo/conditioner. Kitchen is large and has most every appliance you would want. Caretaker does come in twice per day but is friendly and unobtrusive. You do need AWD/4WD to access the house.
Superhost
Flat in Middlebury
4.79 out of 5 average rating, 192 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

rachelRating, 5 stars2 weeks ago
Ideal for a quick college visit. Walkable to campus and breakfast / dinner options. Dog friendly too - exactly what we needed!
Guest favourite
Home in Goshen
4.84 out of 5 average rating, 285 reviews

Nature Lover's Paradise

RobertRating, 5 stars1 week ago
We always love staying here. It’s so peaceful and the sound of the brook is so relaxing! Philip responds quickly and is an excellent host!!
Guest favourite
Home in Rochester
4.98 out of 5 average rating, 203 reviews

The Guest House at Sky Hollow

MargaretRating, 5 stars3 months ago
The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!
Guest favourite
Flat in Montpelier
4.87 out of 5 average rating, 696 reviews

Entire 2nd Floor Walk to Montpelier

IanRating, 5 stars1 week ago
Felt right at home. A nice spacious place for us to stay on our way to Montreal.

Family-friendly home rentals with a pool

Superhost
Apartment in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars2 months ago
Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!
Guest favourite
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

JoshRating, 5 stars1 month ago
Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.
Guest favourite
Apartment in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars1 month ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Top guest favourite
Apartment in Warren
4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars1 month ago
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy
Superhost
Cabin in N. Haverhill
4.92 out of 5 average rating, 164 reviews

Hilltop View Lodge - White Mountains, NH

AndrewRating, 5 stars2 months ago
Our stay was wonderful at the cabin. The cabin was clean and centrally located to winter activities. Andrea was very responsive. Cant wait to go back again
Guest favourite
Apartment in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 weeks ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Superhost
Apartment in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars1 month ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Superhost
Apartment in Killington
4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

ZacharyRating, 5 stars2 months ago
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

Quick stats about holiday rentals that are family-friendly in Randolph

  • Total rentals

    20 properties

  • Total number of reviews

    1.8K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

  • Local attractions

    Shaw's, Al's Pizza & Deli and Saap Restaurant

Destinations to explore