Holiday rentals in Southwick

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Family · Value · Laundry

Lake Views from Hot Tub Propane Fire Pit 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

Value · Location · Bathroom

The Overlook at Lake Congamond

The Overlook is a little bungalow (735 SF) designed with a big hug from the Brady Bunch! Enjoy a fun, retro stay featuring beautiful views of the South Pond of Lake Congamond. Enjoy the fully equipped kitchen, cozy living area, comfortable bedrooms, and deck, all newly renovated. Less than half a mile from the public beach, marina, bike trail, restaurants, bars and other amenities. Near the Berkshires, Bradley Airport & Springfield MA, skiing and hiking, antiquing and so much more.

Family · Location · Getting around

Peaceful Meadow Retreat

Unwind at Meadow's Edge, a serene and cozy refuge where you can come to relax and recharge! Looking out on our peaceful meadow and abutting 125 acres of corn fields, this is a perfect spot to enjoy a book on the shaded back patio, a yoga or meditation session, or a quiet walk through the fields & woods. Take in the view from inside the southern facing windows, where it is not uncommon to see wildlife at dawn or dusk. This is the tranquil getaway that you have been waiting for!

Location · Family · Checkout

Studio ADU Guesthouse near Six Flags

Get ready for thrills and adventure! 🏞️🏰 Our cozy retreat is the perfect base for your Six Flags getaway! 🚗 Located just minutes away from the park, our home offers: Comfortable bedroom with plush bed Fully equipped kitchen for meal prep Relaxing living area for downtime Parking for your convenience Unwind after a day of roller coasters and excitement, and get ready to do it all again the next day! 😎 Book your stay with us and make your adventure unforgettable! 🏠👍

Location · Checkout · Sleep quality

Lake House Retreat Granby CT

Enjoy this private side of a duplex-style home with breathtaking lake views from many rooms and sunroom. Private 3 bedroom, 2 bath plus loft. Large kitchen and dining area. Features shared outdoor space rarely used by owner, plus large entertaining area with grill, games, multiple decks (including private master lakeview deck), hammock gazebo, fire pit, and hot tub. Kayaks available. Starbucks & Dunkin' 5 min away. Vineyards, breweries, waterfalls & bakeries nearby.

Location · Family · Hot tub

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Family · Location · Hot tub

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.)

Value · Location · Hot tub

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.

Value · Location · TV

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

Family · Location · Layout

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!

Family · Location · Back garden

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.

Location · Family · Decor