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

Top of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Okemo Ski Chalet with Hot Tub
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

Okemo-Ludlow, fireplace, hottub, sleeps 13
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

Cozy Award Winning Farmhouse - hot tub and sauna!
Very beautiful home and lovely host! Would recommend!

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.

Large Chalet; Sauna, Hot Tub; Walk to Trail
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.

Ski Chalet with Hot Tub on Okemo Mountain
Great house, location, and host! Eric was very helpful, communited timely, and is super organized. The house is in a great private location right near Okemo, plenty of restaurants, and a grocery store. The house felt bigger than the square footage states and was perfect for our two families (4 adults and 4 kids aged 9-12). We are usually disappointed in how clean rentals are upon our arrival, but this house was basically impeccable which especially isn't easy in the mountains! The upstairs is perfect for a kids room and the living space was nice and cozy, but didn't feel small. Plenty of room for everyone. I highly recommend this house, the hosts, and Okemo. It was our first time on this mountain and really enjoyed the family friendly atmosphere and terrain while also having plenty of advanced trails as well. Overall we had an A+ weekend.

Vermont Getaway Apartment
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!
Family- and pet-friendly home rentals

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

Walk to Village/Lake Whitingham
We went to Vermont to hike and had a wonderful stay with Emily. The place is very cozy and clean. The ability to walk downtown to shops and trails and around a safe, quiet neighborhood was very much appreciated. Beautiful property. Recommended.

Lilac Ridge Farm House
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!

Farm House Apartment on a Working Cattle Farm
What a great weekend getaway. The apartment is cozy with lots of big windows so you can see the farm and cows from inside with the wood stove going, the hosts are so friendly and so are the cows! My group had a blast getting to feed the cows, and meet/brush/sit on Bleu, their big guy! Thank you so much!

The Carriage Barn
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.

Apple Blossom Cottage: A Tiny House
I found this listing years ago while scrolling for tiny houses and it stayed in the back of my mind. I finally had the opportunity to visit as a getaway for my birthday. It was SO peaceful and lovely. I really enjoyed walking the grounds with my dog in lieu of taking a hike nearby, since there was so much rain during my stay. Dominic even let me take a walk to his other property, which was so spacious and pretty as well! I spent most of my time journalling and getting clarity while sitting in the swing on the porch, listening to the rain. I also took a brief voyage to Manchester Center, which was a darling town with lots to explore. I recommend Depot 62 for super tasty Turkish food. The cottage had all the essentials and clear instructions. It could use a deep clean in some of the nooks and crannies, but was overall very tidy and well-kept. I would 100% come back. The vibe up there in the misty mountains of VT is just so high and so freeing. Such a re-aligning stay.

Stone n' Sky Lodge
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.

Rock River Retreat: VT Oasis Pet Friendly
Truly a magical place… the views are amazing. We actually frolicked in the river a bit even though it’s only April and there was small amount of snow on the ground… it was surprisingly refreshing for a feet dip… as far as the unit there was so much charm and care put into this place… we had a snack and beverage awaiting us and Carmella the cat had a snack and toy with a little pillow bed by the window and food dishes ready to use. These extra little touches are special ❤️ The inside is super cute and charming, I loved the bath tub…. I stayed 2 nights and took 3 baths 😂 after our 5 hr drive my daughter needed to use facilities but it took her a good 10 minutes because she loved every detail of the space. I hope to return in summer! Book this space if interested, I promise you will not be disappointed!
Family-friendly home rentals with a pool

The Inn at Quail Run- Guest House
We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.

3 Bedroom Suite at Upper Pass Lodge
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.

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

6 BR Perfect Private Retreat in Vermont!
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

The Villa - Industrial Farmhouse with Hot Tub
We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!

1 Bedroom/1 Bath Condo @ Lake Winnipesaukee
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

Walk to Okemo Ski Lift - Private Classic VT Ski Ch
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.

Bright, Large, Spacious Family Home
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!!
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Mount Sugarloaf State Reservation
- Manchester Country Club - NH
- Bear Brook State Park
- Canobie Lake Park
- Ekwanok Country Club
- The Shattuck Golf Club
- Hooper Golf Course
- Nashua Country Club
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Santa's Land USA
- Crotched Mountain Ski and Ride