Family-friendly holiday rentals in Tolland County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Tolland County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Flat in New Haven
4.75 out of 5 average rating, 141 reviews

Luxury Penthouse Minutes to Yale

AbiolaRating, 5 stars3 weeks ago
My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.
Superhost
Apartment in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars1 month ago
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again
Superhost
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars3 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Guest favourite
Bungalow in Easthampton
4.92 out of 5 average rating, 504 reviews

The Creation Station

KennyRating, 5 stars1 month ago
Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.
Top guest favourite
Home in Stonington
4.97 out of 5 average rating, 228 reviews

Perfect New England Getaway has a pool/ hot tub

DestinyRating, 5 stars1 day ago
Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!
Top guest favourite
Home in Chester
4.97 out of 5 average rating, 351 reviews

Riverfront Getaway

PeterRating, 5 stars3 months ago
Second time staying here, and we continue to love it! The location is great: pretty much anything in western Mass can be reached within about an hour or less from the house. At the house itself, you have a clean, comfortable, and ample space. The hot tub overlooking the river is definitely a highlight. The sounds of the river and the occasional rumble of trains passing by create a beautiful atmosphere. Highly recommended!
Top guest favourite
Home in Colebrook
4.99 out of 5 average rating, 224 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

MichaelRating, 5 stars1 month ago
Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.
Superhost
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars22 months ago
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Family- and pet-friendly home rentals

Guest favourite
Cottage in Middlefield
4.92 out of 5 average rating, 247 reviews

Lake Beseck cottage

MaryRating, 5 stars3 weeks ago
We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!
Top guest favourite
Guest suite in Westerly
4.97 out of 5 average rating, 143 reviews

Room with a View on Spring Pond

RosieRating, 5 stars5 days ago
Linda’s place was a perfect spot to visit Watch Hill, Westerly, Stonington, and Mystic. The pond view is beautiful and Linda was so welcoming and friendly. We brought our dog who was having a bit of separation anxiety and Linda was very understanding. The apartment is lovely and private and well appointed. Highly recommend!
Guest favourite
Guest house in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars9 months ago
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!
Top guest favourite
Cottage in Guilford
4.94 out of 5 average rating, 269 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars2 weeks ago
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!
Guest favourite
Loft in Essex
4.94 out of 5 average rating, 443 reviews

Unique apartment in former art gallery.

JenniferRating, 5 stars3 weeks ago
We loved our stay! It was one of the coolest Airbnb stays our family has enjoyed. Lots of art and ambiance while also being very comfortable with all the amenities you could need. It is an open space (the bedroom walls don’t extend all the way to the ceiling), which didn’t bother us at all but something to be aware of. Thank you Pam!
Guest favourite
Home in Groton
4.99 out of 5 average rating, 139 reviews

Beautiful 3 BR home steps from Downtown Mystic

NancyRating, 5 stars1 month ago
This house was fantastic! We felt right at home. It was immaculately clean and well appointed. Everything you could possibly think of was right at our fingertips . The location is perfect. Everything Mystic is steps away. Highly recommend for anyone looking for a family or friend trip in a great place. And Sheri Ann was very quick to respond to any questions. We’ve stayed in many places and this was undoubtedly the best. 5 Stars.
Top guest favourite
Home in Groton
4.99 out of 5 average rating, 117 reviews

Unique Retreat w/Private Patio, 4 King Beds & BBQ

AngelaRating, 5 stars5 days ago
We had a wonderful family stay a this home to visit some local kid attractions including the aquarium. Hope is a fantastic host - great communication, friendly and accommodating. The house itself was roomy for our group. It was clean and very well appointed with all the basics you need to be comfortable. The four king sized beds was really nice. No fighting over rooms! Our kids enjoyed the chalk and bubbles that were left outside and playing in the yard. The deck is also a nice space although we didn’t get to use it due to weather. I would definitely recommend this home.
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 273 reviews

Charm + location. Walk to beach, town, & harbor.

MaryRating, 5 stars2 weeks ago
Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.

Family-friendly home rentals with a pool

Superhost
Home in New London
4.88 out of 5 average rating, 179 reviews

Waterview Cove 1 @ Ocean Beach: 6 Queen 1 Sofa Bed

CraigRating, 5 stars2 months ago
This place is perfect for a large group with lots of queen size beds. Easy walk to Ocean beach.
Guest favourite
Home in Montville
4.92 out of 5 average rating, 273 reviews

Casino Wine Down House

EsperanzaRating, 5 stars1 week ago
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 238 reviews

Cedar Ridge: House or House+Apartment

HilaryRating, 5 stars1 month ago
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!
Superhost
Apartment in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars7 months ago
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!
Superhost
Flat in Brooklyn
4.85 out of 5 average rating, 221 reviews

8 Bedroom, 4 full bath residence with 40' pool

Maria ChristinaRating, 5 stars1 week ago
The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!
Guest favourite
Home in Ashford
4.87 out of 5 average rating, 78 reviews

Large secluded house in the Woods; Pool, hot tub!

TalRating, 5 stars10 months ago
We came as a group of friends with a baby to stay at Blake and Tracy's house, and we had a great stay. They were very communicative and accommodated all our requests to ensure our stay was excellent. They asked in advance if it would be okay for their child to stay in his room inside the house, and we agreed. We didn’t see him at all during our stay, and it didn’t disturb us in the slightest. The fact that Blake and Tracy live right next door was convenient, as they were readily available for anything we needed, but we never felt their presence. We will definitely come back!
Guest favourite
Home in Brimfield
4.88 out of 5 average rating, 73 reviews

Luxury Home * Pool * Fireplace

DanaRating, 5 stars4 months ago
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

Destinations to explore