Holiday houses in New Milford

4.93 out of 5 average rating, 108 reviews

Apartment in Amenia

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

4.98 out of 5 average rating, 149 reviews

Home in Brookfield

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

4.91 out of 5 average rating, 196 reviews

Guest suite in Watertown

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

4.99 out of 5 average rating, 301 reviews

Guest suite in Bethlehem

Breezy Crest cozy, private retreat near Litchfield

Escape to this charming and historic two-story 1841 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, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Guesthouse in Dover Plains

4.87 out of 5 average rating, 116 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

5 out of 5 average rating, 115 reviews

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 we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. 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!

4.88 out of 5 average rating, 191 reviews

Home in New Milford

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.

4.86 out of 5 average rating, 190 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

4.97 out of 5 average rating, 143 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.95 out of 5 average rating, 204 reviews

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.

4.96 out of 5 average rating, 174 reviews

Guest suite in Sherman

Cozy Scenic New England country retreat w/ hiking

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. Pets welcome. Inquire about min stay requirements.

4.92 out of 5 average rating, 282 reviews

Apartment in Brookfield

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for New Milford holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in New Milford

4.9 out of 5 average rating, 39 reviews

Chalet in New Milford

Candlewood Lake Vacation Home | jj chalet

EmilyRating, 5 stars2 weeks ago

Jessica's place was amazing! It was right by the lake and was easy to get to. There is so much to do in the surrounding area and we had a great time!

Guest suite in Warren

4.78 out of 5 average rating, 225 reviews

Rustic Farmhouse Suite; Cozy; Litchfield County

MarkRating, 5 stars5 days ago

My stay at the homestead was great , Peter is a great host . I picked the homestead to be away from all cities and fish the local river ! This was my second year at Peter’s homestead and enjoyed everyday there . Looking to do a third visit , being in Northwest Conn. is a beautiful sight and feeling .

4.75 out of 5 average rating, 44 reviews

Farm stay in Bethlehem

The Loft @ Sun One Organic Farm

WilliamRating, 5 stars3 weeks ago

This stay was nothing short of incredible. From the moment we arrived, we were blown away by the beauty and uniqueness of the property. The space is immaculately maintained, stylish, and comfortable, with every detail thoughtfully considered. The loft was a standout room—such a cool and unique design that added to the whole experience. Waking up to those stunning views each morning was a dream, and the peaceful, secluded atmosphere made it the perfect escape. The host was communicative, kind, and made everything seamless from start to finish. I can’t recommend this place enough. It exceeded all expectations and made for an unforgettable weekend. Will absolutely be returning to see the other units!

5 out of 5 average rating, 10 reviews

Home in New Milford

Long Mountain Farmhouse

LauraRating, 5 stars4 weeks ago

We rented this house for our family visiting us as our house could not accommodate everyone. Highly recommend - we will try to rent the house again for our family when they visit next time. Can’t say enough about our hosts. Very quick and clear communication. Incredibly friendly and helpful. Everything was great! Thank you!

5 out of 5 average rating, 42 reviews

Guesthouse in Cornwall

Charming Guest Cottage with Private Pool & Hot Tub

TaylorRating, 5 stars4 days ago

Brooke has curated an incredible space. From the amazing stone work surrounding the pool and hot tub to the carefully selected pottery and art dotted around the pool house - everything felt intentional. Brooke and her husband were so accommodating, responsive, and friendly. Her guidebook is excellent, as well. Overall, an amazing stay that is perfect for a couple or pair looking to get away. We definitely hope to return again next summer.

5 out of 5 average rating, 32 reviews

Home in Bridgewater

The Art House: 5-Acre Getaway w/ AC & Firepit

BaileyRating, 5 stars1 week ago

My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!

4.97 out of 5 average rating, 69 reviews

Cottage in New Milford

Waterfront, Wooded Cottage on Candlewood Lake

SofiaRating, 5 stars7 months ago

This spot was absolutely wonderful. The lake was wonderful, fireplace was a perfect touch proximity to the elephants trunk flea market was a dream and don and Roz were a pleasure to work with. Local pizza from a menu in the cabin was perfect. I could write a novel on how much we loved this place. Definitely coming back. It was a pleasure :)