Family-friendly vacation rentals in Hillsborough

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Hillsborough family-friendly rentals

Family-friendly home rentals with a hot tub

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!
Top guest favourite
Home in Colrain
4.94 out of 5 average rating, 176 reviews

Secluded Farmhouse Retreat - stunning views

SophonRating, 5 stars1 week ago
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 favourite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars1 month ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
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 stars2 months 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.
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
Home in Dunbarton
4.9 out of 5 average rating, 31 reviews

Home On The Hill

QiRating, 5 stars2 months ago
We enjoyed the our stay. The house has unique design, kids love it! A very relaxing home like place. Bryan is super responsive and friendly. The house is well equipped with everything we need. Can’t ask for more. Thank you!
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.

Family- and pet-friendly home rentals

Top guest favourite
Cabin in Gilford
4.94 out of 5 average rating, 107 reviews

Tom’s Cabin The Place to be on Lake Winnipesaukee

DionardRating, 5 stars1 week ago
Me and my party enjoyed every minute of our stay at Tom’s cabin! The cabin itself was spacious, cozy, and clean. The surroundings were also beautiful, right next to a nice neighborhood and lake. Thomas was a fantastic host and was extremely friendly and helpful. He was always there to answer questions and help out when needed. Overall, amazing trip and I would 100% go back!
Superhost
Townhouse in Plymouth
4.89 out of 5 average rating, 305 reviews

Tenney/Rumney Ski Townhouse, White Mountains, NH

WeiRating, 5 stars2 weeks ago
Such a nice and quite place! We were enjoying all the time. My cat loves the place with the backyard goes to greens!!! Would definitely love to visit there again!!! Landlords are super responsive and thanks for hosting~
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
Apartment in Loudon
4.9 out of 5 average rating, 606 reviews

A - Farmhouse Apartment on a Cattle Farm

AndrewRating, 5 stars1 day ago
This is a wonderful AirBnb with gracious hosts. Even if your flight is delayed and you arrive in the middle of the night, expect a warm welcome. We had a short stay, but still found time for our daughter to meet some of the farm animals. She loved it. If you’re looking for a quiet spot, with some lovely hosts, this is a fantastic option.
Guest favourite
Home in Salem
4.95 out of 5 average rating, 150 reviews

Quaint Little New Hampshire Lake House Getaway!

LindaRating, 5 stars1 week ago
My husband and I were getting married and in his mind it is customary to not see the bride until she walks down the aisle! On my mind…I didn’t just want to come home, as we live together, just like any other night. I took my mother with me the night before our wedding and fell in love with this cute, quiet place with a gorgeous view, again nothing too far from our venue. We had worked out a little confusion on communication, we were great and going to have the cutest little house overlooking a pond/lake! My mother loved it and my husband loved it as well. It was very well kept, gorgeous view out the ceiling to floor windows! Private, quaint, easy to get to, quiet….just super cute all around! My husband and I do Airbnb‘s a couple times a year….if we were to look for some place close to home, we would definitely love to stay here again! Everything was great!
Top guest favourite
Barn in Guilford
4.99 out of 5 average rating, 122 reviews

The Carriage Barn

EllenRating, 5 stars3 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.
Top guest favourite
Apartment in Newfane
4.97 out of 5 average rating, 449 reviews

Rock River Retreat: VT Oasis Pet Friendly

AshleyRating, 5 stars3 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!
Top guest favourite
Apartment in Peterborough
4.92 out of 5 average rating, 189 reviews

Private Apartment with a Mt. view

BradRating, 5 stars3 months ago
Cold Comfort Farm offers a wonderful setting and view for anyone who wants a true New Hampshire experience. It reminded me of my youth growing up nearby. Jo was completely welcoming.

Family-friendly home rentals with a pool

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
Condo 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
Superhost
Condo in Quechee
4.88 out of 5 average rating, 90 reviews

Condo on Quechee Golf Course with Private Feel

JackRating, 5 stars5 months ago
It was so great staying at Corey’s place! It was just liked described and it was a great launch pad to explore Quechee and the surrounding area. We enjoyed it so much and would love to go back!
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!!
Superhost
Home in Hartford
5 out of 5 average rating, 25 reviews

The Fairway House - Premier Golf Course 3 BR Home

JanetRating, 5 stars20 months ago
We thoroughly enjoyed our stay with 5 adults and one dog. We walked in and immediately felt at home. This was one of the most well appointed places I have ever rented...it had everything we needed and more . The kitchen and the living space was quite comfortable. The beds were wonderful. There is a trail to the river right across the street which we used several times. I can't think of a negative thing to say.
Guest favourite
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars3 weeks ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Guest favourite
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!

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