Family-friendly holiday rentals in Stoddard

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Popular amenities for Stoddard 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 stars2 months ago
Nice place thanks Mike
Guest favourite
Chalet in Ludlow
4.94 out of 5 average rating, 127 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars1 month ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Superhost
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars1 month ago
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.
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 favourite
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 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.
Top guest favourite
Home in Ludlow
4.97 out of 5 average rating, 158 reviews

Ski Chalet with Hot Tub on Okemo Mountain

MichaelRating, 5 stars1 month ago
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.
Guest favourite
Flat in Londonderry
4.96 out of 5 average rating, 580 reviews

Vermont Getaway Apartment

JoshuaRating, 5 stars1 month ago
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

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

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

JamesRating, 5 stars2 months 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!
Guest favourite
Loft in Wilmington
4.91 out of 5 average rating, 200 reviews

Walk to Village/Lake Whitingham

LeslieRating, 5 stars4 days ago
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.
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 favourite
Flat in Loudon
4.9 out of 5 average rating, 605 reviews

Farm House Apartment on a Working Cattle Farm

NicoleRating, 5 stars1 week ago
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!
Top guest favourite
Barn in Guilford
4.99 out of 5 average rating, 121 reviews

The Carriage Barn

EllenRating, 5 stars2 weeks 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 favourite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,259 reviews

Apple Blossom Cottage: A Tiny House

AveryRating, 5 stars2 days ago
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.
Top guest favourite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
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.
Top guest favourite
Flat in Newfane
4.97 out of 5 average rating, 449 reviews

Rock River Retreat: VT Oasis Pet Friendly

AshleyRating, 5 stars2 weeks ago
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

Superhost
Guest house in Wilmington
4.96 out of 5 average rating, 24 reviews

The Inn at Quail Run- Guest House

MargaretRating, 5 stars23 months ago
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.
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 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!
Guest favourite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars9 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 favourite
Home in Dover
5 out of 5 average rating, 58 reviews

The Villa - Industrial Farmhouse with Hot Tub

StephanieRating, 5 stars3 months ago
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!
Top guest favourite
Apartment in Laconia
4.94 out of 5 average rating, 155 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 favourite
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 stars6 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!!

Destinations to explore