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

Villa Flora @ Norwich Inn & Spa
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson
A beautiful, cozy, very well-stocked home. Remote enough to feel like you're in the country but in proximity to so many great activities on offer in Copake and Hudson. A special place. We had a wonderful stay.

The Creation Station
John was incredible and so hospitable. His home was beautiful and well kept. Very responsive and one of the best weekends of the weekend ! 11/10 recommend :)

(°) The Wandering Peacock (°)
I went for my boyfriends 25th birthday it was absolutely stunning from all of the art everywhere in the house and outside! We stayed in the sauna from when we got there till late at night it was an absolutely wonderful experience even just for a night!

Unwind in the country, stargaze in hot tub
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.

The Farmhouse - Hot tub eclectic farmhouse 3 br
A peaceful location with chill activities for all ages...we enjoyed the phonograph, the retro Atari, the hot tub, the window bird feeder, and watching birds in the spacious yard and conservation area. Herons, hawks, and songbirds viewed. The hot tub was sparkling clean, and the linen robes were a thoughtful touch. Wifi worked great. We arrived late but instructions for entry were crystal clear. Virginia answered my questions promptly and warmly. Definitely a winner.

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.
Family- and pet-friendly home rentals

Columbia County Getaway - Raspberry Ridge Cottage
The place is ideal, even if the weather isn't great the house is really spacious and cozy. Laurence and Ilze were communicative and very sweet, would love to come back!

Cedar Wet Room w Soaking Tub
It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.

Guesthouse close to hiking, shopping and ski!
Donna's place was a wonderful weekend stay! Beautiful property and guest house. Well appointed and care for. Just a few improvements that would have made our stay even better--a small microwave for quick reheating of coffee/leftovers, a luggage rack and place to store/hang clothes, and ensuring the driveway and a walking path are cleared of snow even when out of town (with thawing and refreezing, we had to navigate two inches of solid ice, which was terrifying both on foot and in the car).

Secluded Post-And-Beam Retreat
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

Litchfield County Getaway
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend

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.

3 bedroom near Wesleyan, downtown
Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!

Cozy Little Cottage
My daughter and I loved our stay so much. The setting is so beautiful and peaceful. I loved listening to all the bird song and my daughter loved the fish! Such a cozy, comfortable home. We loved our relaxing time here. Gabriele is a fabulous host, so responsive and so kind. Thank you!!
Family-friendly home rentals with a pool

Casino Wine Down House
House was very easy to get to and very clean. Surrounding neighborhood was nice and quiet. Outside igloo was warm and cozy. Downstairs game room was a hit with the big kids.

Cozy private apt 8 mins from UCONN - solar powered
This is a wonderful place to stay if you are visiting UConn or the surrounding area. Keri and Jason were fabulous hosts and very responsive to my needs. Keri even anticipated needs by offering to have a fresh cup of coffee ready for me on the AM. Everything was perfect for my stay and there was definitely a comfortable feel. I will definitely be staying here in the future.

Pool House
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

Cedar Ridge: House or House+Apartment
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!

Affordable In-Law Apartment in Brooklyn, CT
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!

8 Bedroom, 4 full bath residence with 40' pool
This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Great place. As described. Met our expectations.

Berkshire Lake House, gunite pool, Chef's Kitchen
Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags New England
- TPC River Highlands
- Taconic State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Sleeping Giant State Park
- Mount Southington Ski Area
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Rockledge Golf Club
- WIckham Park
- Bright Nights at Forest Park
- Brimfield State Forest