Family-friendly vacation rentals in Stoddard

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Stoddard family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Killington
4.9 out of 5 average rating, 92 reviews

Brookview Lodge, Killington, VT

TylerRating, 5 stars4 weeks ago
Great place to stay for access to Killington. hot tub was great to relax in and living room was cozy after skiing.
Superhost
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars1 month ago
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!
Guest favorite
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
Top guest favorite
Home in Colrain
4.94 out of 5 average rating, 176 reviews

Secluded Farmhouse Retreat - stunning views

SophonRating, 5 starstoday
This was a great home away from home. Wish it didn’t rain as much as it did. We really wanted to walk the grounds more. Inside was cozy and warm. Anything you needed it was there. Definitely thinking about coming back in the winter because it would be a perfect winter wonderland. Thanks again Sophon
Guest favorite
Chalet in Ludlow
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars3 weeks ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Superhost
Farm stay in Londonderry
4.82 out of 5 average rating, 136 reviews

Cozy Award Winning Farmhouse - hot tub and sauna!

JumanaRating, 5 stars12 months ago
Very beautiful home and lovely host! Would recommend!
Top guest favorite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars1 month ago
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.
Guest favorite
Home in Dunbarton
4.9 out of 5 average rating, 30 reviews

Home On The Hill

RileyRating, 5 stars2 months ago
Bryan and Monica are excellent hosts and myself and those who stayed had an awesome experience over the course of the 6 weeks we spent at their location. We would highly recommend staying at their properties and plan on spending more time in the area again soon.

Family- and pet-friendly home rentals

Guest favorite
Cabin in Jamaica
4.88 out of 5 average rating, 112 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

JamesRating, 5 stars1 month ago
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!
Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Guest favorite
Apartment in Loudon
4.9 out of 5 average rating, 604 reviews

Farm House Apartment on a Working Cattle Farm

Helen RebeccaRating, 5 stars2 weeks ago
I’m in love with this place! Highly recommend and I will definitely be back. Love the deck overseeing the hills and the fireplace that kept us cozy indoors! The place was pristine!! The cows alone are worth the trip. Good for a group of friends or a family trying to have a relaxing weekend! No regrets!!
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 182 reviews

Apartment on Main Street

WinnieRating, 5 stars4 weeks ago
This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.
Guest favorite
Home in Jamaica
4.81 out of 5 average rating, 405 reviews

1850's VT Farmhouse on the River

MichaelRating, 5 stars6 months ago
We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.
Top guest favorite
Barn in Guilford
4.99 out of 5 average rating, 121 reviews

The Carriage Barn

EllenRating, 5 stars1 week ago
We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.
Guest favorite
Home in Shelburne Falls
4.93 out of 5 average rating, 100 reviews

Buckland House - A World Apart

LizRating, 5 stars7 months ago
House is really awesome! We had a fantastic time. Definitely recommend.
Guest favorite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,256 reviews

Apple Blossom Cottage: A Tiny House

JulieRating, 5 stars4 days ago
We enjoyed our stay at Domenic with 2 kids on school break! The tiny house is just as described, colorful, well organized and very comfortable. We enjoyed making a fire outside on a beautiful spring evening and checking out the peacocks!

Family-friendly home rentals with a pool

Superhost
Bed and breakfast in Londonderry
4.8 out of 5 average rating, 5 reviews

3 Bedroom Suite at Upper Pass Lodge

StevenRating, 5 stars16 months ago
The staff of Upper Pass lodge was super friendly and helpful! From the hotel staff, restaurant crew, and house keeping- everyone was fantastic. They really take Vermont hospitality to the next level. We hope to visit with them again soon.
Guest favorite
Condo 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!
Guest favorite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars8 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Top guest favorite
Condo in Laconia
4.94 out of 5 average rating, 154 reviews

1 Bedroom/1 Bath Condo @ Lake Winnipesaukee

JeremyRating, 5 stars1 month ago
Mikes place was a great stay while in. New Hampshire. Lots of stuff to do on the lake and everything you need is within walking distance!! I nightly recommend this condo on the lake
Guest favorite
Home in Ludlow
4.91 out of 5 average rating, 98 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

MeredithRating, 5 stars2 months ago
Our family really enjoyed our stay at the trailside chalet! A quick walk up the road to the ski lifts and plenty to keep us entertained after a day of skiing. We really enjoyed the fire place and pool table!! Prescott was a great host, quick to respond to our questions.
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars5 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Guest favorite
Condo in Ludlow
4.93 out of 5 average rating, 109 reviews

One Bedroom Suite Near Okemo

ElizabethRating, 5 stars4 weeks ago
Great little studio . Lots of nearby dining options, and a short drive to Okemo.
Guest favorite
Home in Woodstock
4.97 out of 5 average rating, 59 reviews

Dana Road House Sunlit VT Country Home w/HotTub

EstherRating, 5 stars4 months ago
Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!

Destinations to explore