Family-friendly holiday rentals in Newtown

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Huckleberry Quarters, the Cozy Redding Retreat.

It’s time to book your Winter holiday at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming two-story suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, under 30 min to Mohawk and just 90 miles from NYC, you'll have easy access to winter fun!

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

Stylish Studio with Kitchen, Central Danbury

‣ Fully Furnished Studio Apartment with kitchenette - Cooktop but no oven ‣ Central Location ‣ Walking distance to Starbuck, C-town, Ridgewood Country Club ‣ Close to the highway (some guests say you can hear cars passing by on the highway) ‣ 2 minutes from Interstate 84 ‣ 15 minutes to Danbury Fair Mall ‣ .5 miles or a 5 to 10 mins walk to food shopping