Holiday houses in Warren

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Top-rated holiday rentals in Warren

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Lush green trees frame a serene view of Lake Waramaug, with gentle hills rising in the background. The water reflects the clear sky and surrounding foliage, creating a calming natural scene inviting relaxation and outdoor activities.
Home in Warren
4.86 out of 5 average rating, 7 reviews

Modern country home - views and lake access & Ski

Have fun with the family at this modern country home with views of Lake Waramaug and private boat house and dock. Ski Mohawk. 2 hours from nyc escape to a 4 bedroom 3.5 bath renovated home with all the features of a great family escape! From fire pit and fun summer games to views of the lake, access to the best town beach on lake Waramaug 10 minute drive to Washington depot, new preston, Litchfield. 5 minute drive to town beach and 5 minute drive to our private dock for boating and swimming.

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
5 out of 5 average rating, 110 reviews

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!

Top Guest favourite
An elegantly set dining table displays black plates, clear glassware, and cloth napkins. A lit candle adds a soft glow, while a modern kitchen is visible in the background, featuring stainless steel appliances and a cozy living area with seating.
Holiday home in Warren
4.98 out of 5 average rating, 220 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Top Guest favourite
A split-level ranch home sits on a gently sloped hill surrounded by trees. The structure features a distinct two-car garage attached to the main house. A blue sky with scattered clouds provides a bright backdrop, enhancing the natural setting.
Home in Warren
4.95 out of 5 average rating, 22 reviews

The Mountain Laurel Overlook

Tucked away on 2.5 wooded acres, this charming country home sits on a hill with abundant natural light. The spacious back patio overlooks a beautiful tree-lined yard teeming with wildlife. Private, peaceful, and full of rustic character, it offers a unique escape from the everyday. Only 10-30 minutes away from all of Litchfield County's best including highly-rated restaurants, swimming at Lake Waramaug State Park, the CT Wine Trail, unique local shopping, hiking the Appalachian Trail & more!

Top Guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 132 reviews

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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
5 out of 5 average rating, 104 reviews

Fully Renovated Rural Barn

Newly renovated 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 in a dedicated driveway.

Top Guest favourite
Home in Warren
5 out of 5 average rating, 32 reviews

Modern Timber Frame Colonial Saltbox

Take it easy at this unique and tranquil getaway. Carefully crafted timber frame colonial Saltbox with modern amenities. Tucked away on 90+ acres and dead end road. Property features a brook, sweeping pasture, and stone walls. Wander the grounds or explore the area: top restaurants, hiking, wineries, and skiing. Proximate to the best towns of Litchfield County: only three minutes to Warren town, 10 minutes to New Preston, 12 minutes to Kent Barns, and 16 minutes to Washington Depot.

Top Guest favourite
An open living area features a dark couch adorned with decorative pillows. Natural light floods through large sliding glass doors that provide views of the outdoors. A dining space with a table for six is visible, accompanied by a staircase leading to the upper level.
Home in Warren
5 out of 5 average rating, 30 reviews

Magical Woodland Getaway

Tucked in the Litchfield Hills our home promises a serene getaway. Just 2 hrs from NYC, our post + beam home is nestled on two beautiful + private acres where you can enjoy your morning coffee while listening to the babbling brook, spend the day hiking, exploring the idyllic towns of NW CT, swimming at Lake Waramug or skiing at Mohawk MTN, and in the evening, you can enjoy a homemade dinner or indulge at a nearby restaurant, ending your night with a glass of wine around the fire pit.

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
4.95 out of 5 average rating, 247 reviews

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.

Top 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
4.98 out of 5 average rating, 181 reviews

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!

Top Guest favourite
Guesthouse in Cornwall
5 out of 5 average rating, 67 reviews

The Pool Cottage at Narrow Valley Estate

Nestled in a narrow valley in Litchfield County, this charming guest cottage is located on a stunning 275 acre estate at the end of a mile long private drive. With its own private pool and hot tub nestled within stone walls, it is perfect for couples looking for a romantic retreat, or individuals looking to rest and regroup from too much work. It is a 2+ miles to the village of Cornwall, and a 25 minute drive to Litchfield, Kent, Sharon, and Falls Village.

Top Guest favourite
The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.
Cottage in Pawling
4.99 out of 5 average rating, 177 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Popular amenities for Warren holiday rentals