
Family-friendly vacation rentals in Southwick
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Top-rated family-friendly rentals in Southwick
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Rustic Pond Cabin: Nature, Stars & Serenity
🦉Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. All natural pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay n walk the trail around the pond, have campfires outside in firepit! Clean & no crazy rules! Surrounded by acres nature! Private-Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!🦉
4.95 out of 5 average rating, 130 reviews
Lake Views from Deck Fire Pit & Hot Tub 4 Kayaks
Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport
4.98 out of 5 average rating, 168 reviews
Onomea Farm
Relax and watch the sheep graze in the pasture. Enjoy the amazing night sky. Fabulous modern two bedroom handicapped accessible in law suite with separate entrance. Fireplace, washer/dryer, heat, central A/C. King adjustable bed on main level, King and pull out sofa on 2nd floor. Both bedrooms have 50” TV’s. Full kitchen. Located in North Granby, CT. Quiet location yet close to major attractions and Bradley airport. We have 8 resident well behaved dogs THAT RUN FREE on the property -
4.96 out of 5 average rating, 132 reviews
Farm Stay with Horses & Pool | Mountaintop Views
Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.
4.97 out of 5 average rating, 143 reviews
Farm Fresh Feeding Hills
Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.
4.89 out of 5 average rating, 1054 reviews
South Quarter House
Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)
4.97 out of 5 average rating, 310 reviews
The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John
4.93 out of 5 average rating, 585 reviews
Sunrise on the Water's Edge - Riverside Bungalow
Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.
4.97 out of 5 average rating, 259 reviews
10 Hillcrest
So we were offline for a few months but we now have a totally new remodeled space. Lots more light and upgrades we think you will enjoy! The perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street! Many, many farms, wineries, breweries and eateries just minutes down the road. We are also just minutes from Bradley International Airport
4.85 out of 5 average rating, 434 reviews
Windy Top Cottage ~ A Romantic "European" Getaway
The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!
4.98 out of 5 average rating, 932 reviews
The Little Red Schoolhouse ~ Circa 1877
This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.
4.87 out of 5 average rating, 263 reviews
Treehouse - Countryside - Farm Animals - Fire Pit
Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)
4.93 out of 5 average rating, 549 reviewsPopular amenities for Southwick family-friendly rentals
Family-friendly home rentals with a hot tub

4 BR Entire House w/Hot Tub
4.99 out of 5 average rating, 110 reviews
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
4.99 out of 5 average rating, 252 reviews
Fall Foliage Luxury Cabin & View Autumn Adventures
4.97 out of 5 average rating, 110 reviews
Jaw dropping mountain & lake views
4.96 out of 5 average rating, 311 reviews
Luxe Bolton Lake
4.99 out of 5 average rating, 186 reviews
HOT TUB! Dog & Family Friendly in the Berkshires!
4.94 out of 5 average rating, 135 reviews
Berkshires Lodge | Pool, Hot Tub & Fire Pit
4.86 out of 5 average rating, 118 reviews
Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away
4.98 out of 5 average rating, 195 reviewsFamily- and pet-friendly home rentals

Elegant 3BR Longmeadow Home| Sauna| Near Big E
4.78 out of 5 average rating, 256 reviews
Light filled three bedroom apartment DT Florence!
4.97 out of 5 average rating, 498 reviews
Guesthouse Farm Stay
4.97 out of 5 average rating, 358 reviews
Berkshire Treehouse Retreat
4.91 out of 5 average rating, 181 reviews
A Tranquil Getaway Wrapped in Island Vibes
4.92 out of 5 average rating, 111 reviews
Trainmaster's Inn - Caboose
4.94 out of 5 average rating, 142 reviews
Berkshires Cottage by Lake. Year Round Adventures.
4.95 out of 5 average rating, 320 reviews
Serene 1-br suite on 75 acre horse property
4.98 out of 5 average rating, 174 reviewsFamily-friendly home rentals with a pool

Close AirPort|SixFlags|Big E|Free Private Parking
4.9 out of 5 average rating, 106 reviews
FROG Suite Apartment
4.99 out of 5 average rating, 344 reviews
1880s bright sun+design in best downtown location
4.97 out of 5 average rating, 419 reviews
Stunning Views, Bucolic Bliss in 1790s Farmhouse
4.93 out of 5 average rating, 213 reviews
Cozy private apt 8 mins from UCONN - solar powered
4.95 out of 5 average rating, 244 reviews
Enjoy every season the Berkshires have to offer.
4.96 out of 5 average rating, 134 reviews
Berkshire Getaway Ranch 3 acres + saltwater pool
4.93 out of 5 average rating, 109 reviews
Sunlit Cozy Cabin 8 Private Acres By Colleges
4.96 out of 5 average rating, 324 reviewsDestinations to explore
- New York City Vacation rentals
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Ski Sundown
- Wesleyan University
- University of Massachusetts Amherst
- Naumkeag
- Norman Rockwell Museum
- Mount Southington Ski Area
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Devil's Hopyard State Park





