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Family-friendly holiday rentals in New Milford

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Quick stats about holiday rentals that are family-friendly in New Milford

  • Total holiday rentals

    Explore 100 holiday rentals in New Milford

  • Nightly prices starting at

    New Milford holiday rentals start at $112 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,010 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 of New Milford holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across New Milford rentals

  • 4.9 Average rating

    New Milford stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in New Milford

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

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Top Guest favourite
A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.
Barn in Roxbury

Luxury Rural Barn

Renovated luxury barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking is in the dedicated driveway.

FamilyKitchenCleanliness

5.0 out of 5 average rating, 110 reviews
Top Guest favourite
A warm wooden interior is highlighted by a charming dining area featuring a small table set for two. Natural light streams through double doors, revealing scenic views outside. Soft curtains adorn the windows, and a small kitchenette is visible in the background.
Guest suite in Sherman

Cozy Scenic New England rural retreat hike & kayak

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian Trail & other great hiking. Family friendly beach on Lake nearby. Pets welcome. Inquire min stay requirements.

KitchenFamilyCheck-in

4.96 out of 5 average rating, 191 reviews
Top Guest favourite
A spacious deck features a traditional wood-burning hot tub, reflecting the surrounding trees and sky. Nearby, a dining set provides a place to enjoy meals outdoors, surrounded by the natural beauty and serenity of the cabin's setting.
Cabin in New Milford

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Indoor spacesKitchenLayout

5.0 out of 5 average rating, 112 reviews
Top Guest favourite
A serene river view is framed by tall trees, creating a natural canopy overhead. In the foreground, two Adirondack chairs are positioned on the grassy bank, inviting relaxation while overlooking the calm water surrounded by lush greenery.
Home in New Milford

Idyllic retreat on the water <1.5 hrs to NYC.

Private getaway on 3+ acres on the river with no visible neighbors, sit by the river or in the enclosed patio with view of the water, walk the trails in the area. Great for short escapes or longer discounted stays enjoy great restaurants, antiquing, swimming, hiking, and access to all New England has to offer. In spring, summer and fall lots of open air activities to be had. Fishing, boating, farmers markets and flea markets. In winter many nice walks to be had, skiing is not too far away.

FamilyKitchenNearby

4.97 out of 5 average rating, 134 reviews
Top Guest favourite
An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.
Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.

Indoor spacesFamilyWi-Fi

4.95 out of 5 average rating, 103 reviews
Guest favourite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Indoor spacesKitchenWi-Fi

4.94 out of 5 average rating, 252 reviews
Top Guest favourite
A welcoming living area features a green sofa positioned next to large glass doors that open to a view of the outdoor surroundings. A round side table is placed nearby, and natural light fills the space, highlighting the warm wooden walls and floor.
Guesthouse in New Milford

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

KitchenIndoor spacesLocation

4.98 out of 5 average rating, 124 reviews
Guest favourite
The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.
Home in Cornwall

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

FamilyIndoor spacesCheck-in

4.97 out of 5 average rating, 188 reviews
Top Guest favourite
A serene view of Squantz Pond is framed by lush greenery, with vibrant trees and neatly trimmed grass in the foreground. The tranquil water reflects the sky, creating a peaceful atmosphere, while a private dock is visible along the water's edge.
Home in New Fairfield

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!

FamilyIndoor spacesBackyard

4.93 out of 5 average rating, 132 reviews
Top Guest favourite
An aerial view captures a sprawling farm landscape at sunset, with the sun dipping behind rolling hills. The guest house, white with a gray roof, is surrounded by green fields and lush vegetation, creating a serene atmosphere.
Farm stay in New Milford

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers that is sold at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, and chickens. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

FamilyKitchenHeating

5.0 out of 5 average rating, 143 reviews
Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

FamilyIndoor spacesTV

4.96 out of 5 average rating, 458 reviews
Top Guest favourite
A cozy living room is furnished with two gray sofas and a patterned armchair. A wooden coffee table sits in the center, complemented by a decorative plant. Natural light enters through large bay windows, highlighting the space's warm, neutral tones.
Home in Sherman

Slice of Paradise in the Country

Our "Slice of Paradise in the Country" is the perfect place to relax, unwind, and get away from it all. Whether you're visiting family or friends in the area, looking forward to some hiking/skiing/dining out/shopping, or seeking a beautiful setting to concentrate on finishing up some work, our home has absolutely everything you'll need for a comfortable and memorable stay.

Indoor spacesKitchenSleep quality

5.0 out of 5 average rating, 110 reviews

Popular amenities for New Milford family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A sunlit enclosed sunroom features a curved sectional sofa adorned with decorative pillows and a central wooden table. Large windows invite natural light, offering views of the backyard. A rocking chair and potted plant add a cozy touch to the inviting space.
Home in Dover Plains

Hillside Grove

KitchenIndoor spacesAir conditioning

4.96 out of 5 average rating, 100 reviews
Top Guest favourite
A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.
Farm stay in Kent

(°) The Wandering Peacock (°)

Indoor spacesFamilyView

4.88 out of 5 average rating, 370 reviews
Top Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 170 reviews
Superhost
A two-story house with light green siding and contrasting dark shutters stands amidst a natural landscape. The front entrance features a covered porch and bright red door. A two-car garage with red doors complements the exterior, bordered by landscaped bushes and flowering plants.
Cottage in Kent

Adventure Basecamp - Hot Tub - Mohawk Mtn

FamilyIndoor spacesLocation

4.8 out of 5 average rating, 294 reviews
Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

Indoor spacesKitchenComfort

4.81 out of 5 average rating, 136 reviews
Top Guest favourite
Campervan/RV in Wassaic

Glamp in a 1970s Airstream | Hot Tub | NYC Train

KitchenIndoor spacesHot tub

4.99 out of 5 average rating, 100 reviews
Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

Indoor spacesKitchenLaundry

4.88 out of 5 average rating, 220 reviews
Guest favourite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Indoor spacesKitchenBarbecue

4.96 out of 5 average rating, 145 reviews

Family- and pet-friendly home rentals

Top Guest favourite
Apartment in Holmes

Top Side

FamilyIndoor spacesPets

5.0 out of 5 average rating, 143 reviews
Top Guest favourite
Cabin in Cornwall

Beautiful country house in Cornwall CT.

FamilyIndoor spacesAccess

4.98 out of 5 average rating, 104 reviews
Top Guest favourite
Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

Indoor spacesKitchenSleep quality

4.99 out of 5 average rating, 104 reviews
Top Guest favourite
Home in Newtown

Comfortable home away from home- near everything

Indoor spacesFamilyDecor

4.99 out of 5 average rating, 147 reviews
Guest favourite
A light-filled living area features a white sectional sofa and natural decor. Shelves with decorative items and plants enhance the space. The open layout leads to a dining area visible in the background, with wooden furniture and a textured rug grounding the room.
Home in Bethel

Boho house near NYC

FamilyKitchenParks

4.85 out of 5 average rating, 123 reviews
Top Guest favourite
The dining area features a wooden table covered with a floral tablecloth, accompanied by black chairs. Exposed wooden beams adorn the ceiling. Large windows allow natural light to fill the space, while shelves display decorative items in the background.
Cottage in Washington

Litchfield Hills Country Hideaway

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 115 reviews
Top Guest favourite
Two dome homes are nestled among lush greenery, connected by a spacious wooden deck. Soft outdoor lighting highlights the natural landscape, while the architecture features large arched windows. A pathway leads through well-maintained garden beds, enhancing the tranquil setting.
Cabin in Cornwall

Vibrant, secluded dome home in Litchfield County!

Indoor spacesKitchenWi-Fi

4.93 out of 5 average rating, 225 reviews
Top Guest favourite
A rustic farmhouse exterior showcases a wooden façade with red double doors and a welcoming balcony adorned with potted flowers. The balcony is accessed by wooden steps, leading to a charming outdoor seating area. Seasonal foliage decorates the surrounding landscape.
Farm stay in West Simsbury

Flamig Farm Staycation

FamilyKitchenPets

4.96 out of 5 average rating, 555 reviews

Family-friendly home rentals with a pool

Guest favourite
A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.
Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

KitchenFamilyLayout

4.93 out of 5 average rating, 212 reviews
Top Guest favourite
An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.
Barn in Bethel

Escape to a Restored New England Antique Milk Barn

KitchenIndoor spacesView

4.98 out of 5 average rating, 266 reviews
Top Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

KitchenIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 187 reviews
Top Guest favourite
A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.
Barn in Bloomfield

Farm Stay with Horses & Pool | Mountaintop Views

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 139 reviews
Top Guest favourite
The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.
Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

FamilyIndoor spacesPool

4.98 out of 5 average rating, 176 reviews
Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Indoor spacesKitchenValue

4.95 out of 5 average rating, 135 reviews
Guest favourite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

FamilyIndoor spacesHospitality

4.99 out of 5 average rating, 329 reviews
Guest favourite
An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.
Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

KitchenIndoor spacesWi-Fi

4.82 out of 5 average rating, 107 reviews

When is the best time to visit New Milford?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$409 AUD$399 AUD$369 AUD$404 AUD$483 AUD$529 AUD$624 AUD$638 AUD$488 AUD$484 AUD$446 AUD$424 AUD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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