Family-friendly holiday rentals in New Fairfield

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Top-rated family-friendly rentals in New Fairfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home

4.94 out of 5 average rating, 136 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Superhost

Guest house

4.92 out of 5 average rating, 204 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Guest favourite

Cabin

4.96 out of 5 average rating, 417 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Superhost

Home

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Guest favourite

Home

4.95 out of 5 average rating, 349 reviews

Winter Wonderland: Dog & Family Friendly Chalet

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favourite

Home

4.92 out of 5 average rating, 111 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guest favourite

Cabin

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just opened availability for Christmas and New Years Week! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” (ha!) and super chic Inness.

Superhost

Cottage

4.88 out of 5 average rating, 519 reviews

Mod Scandinavian! Tiny Flower Farm

Minimalistic Cottage with spacious decks. Clean, Comfortable. Mountain Views! Perfect location. Sustainable. Stars!! Activities activities. Hiking, skiing!! Yes, it's beautiful and memorable! Amazing views. Minutes to Mohonk, Minnewaska, Skiing. Tall windows for brilliant views. Kitchen w/Italian granite,tiled shower. Enjoy, take care of it. Leave as found, pls! We love it! Hope you will too! Pls read detailed listing and house rules. 🩷😊

Guest favourite

Farm stay

4.87 out of 5 average rating, 337 reviews

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

Guest favourite

Home

4.98 out of 5 average rating, 230 reviews

Storybook Cape...HOST & Co.

A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where you can enjoy antiquing, dining, shopping, and relaxing in the picturesque town center. If hiking and outdoor activities are more your thing we are also minutes from White Memorial Foundation and Topsmead National Forest is right around the corner. Mohawk Mountain Ski Area is 12 miles away.

Guest favourite

Flat

4.87 out of 5 average rating, 293 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Guest favourite

Home

4.95 out of 5 average rating, 129 reviews

Family weekend getaway

Two bedroom home located in Beacon. Mt. Views from living room and dining room windows. Close to mt. and Main st. Children welcome. Baby items available pack n play, bouncy seat, swing. Bear Mt and West Point within driving range. Extra charge for pets $100.00. Four adults or families up to 6.