Family-friendly holiday rentals in Southbury

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

Loved this house! We have stayed in many places all over the world for both business and pleasure. This was a business trip. House was great, location was great. It was cold and rainy so we didn’t get to enjoy the porch, deck or hot tub . Even without these amenities we totally enjoyed the house. Hoping to stay again next time we are in the area. We are in Rhinebeck twice a year for the antiques show in the Fairgrounds . Instructions on house were easy to understand and concise. Great job guys!

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

Abigail is an incredible host. She is super accommodating and communicative. She is the sweetest and her home is incredible. This place is definitely worth it. Beautiful space and a wonderful experience.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

We had a great and easy stay for a quick upstate weekend! The house was clean, cute, and accommodated our family of 7. We unfortunately didn’t get to utilize the outdoors because of the weather. Would definitely recommend this house!

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.

Just what we needed for a relaxing weekend. Place was clean and comfortable. Situated in the woods- scenic, quiet and relaxing with the sound of the creek down below. Rainy weekend but it was dreamy looking out the large floor to ceiling windows. Highly recommend this place if youre looking for a quiet getaway. Rhinebeck Village and Red Hook shops are within 20-30 min drive.

Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.

Very nice apt and perfect for a quick weekend getaway.

This is our second time staying here, conveniently located. Very comfortable accommodation for me and my family. Will definitely stay here again!

Juliana and Paul were great hosts! There was a storm the day we arrived and they communicated about the towns power outage before our arrival. They had generators on hand and Paul set up the generator and had many extension cords, flashlights and called local supermarkets/restaurants for us. Luckily the outage was just a few hours. The place was clean and spotless. It was quiet and a short drive into Main Street where you can find restaurants. It is close to many beautiful hikes. We would certainly return as it was a joy to stay in such a peaceful home.

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

We stayed at Monica's place multiple times when visiting my son at Wesleyan. We loved it! We appreciated the convenience of the location and ease of parking. We wish we had found it sooner because we had been staying at hotels 15-30 minuets away. The apartment is as shown and has always been clean. Its comfortable, has everything needed and is no fuss. We enjoyed inviting people over between activities on campus. Monica is very responsive and helpful and kind. She has a beautiful garden and a sweet sitting area outside for when the weather is nice!

I almost didn’t want to write a review so people don’t book this place…. But I definitely have to. It was such a blast. We collected eggs in the morning, we tried peacock eggs for breakfast. They had an amazing playground, and awesome cats and dogs running around the farm. The fact that we got the farm to ourselves after hours was so memorable. My first airbnb and probably will put other airbnbs expectations high.

We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

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!

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

Alice’s place was great! We’ll be back again for sure.

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.