House vacation rentals in Kent

4.96 out of 5 average rating, 105 reviews

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

Country hillside retreat. Expansive outdoor patio area complete with Blackstone grill and hot tub. A cozy deck with casual seating nestled amongst the trees and an exquisite natural stone fire pit with six adirondack chairs. An enclosed sunroom overlooking expansive property and sunset. A large harvest table with seating for 8 in the main dining area for more formal gatherings. Fully equipped, recently renovated kitchen and a sitting room for enjoying morning coffee or tea. Large family room.

4.96 out of 5 average rating, 166 reviews

A charming red cottage is surrounded by trees displaying autumn foliage. The structure features white trim and a star accent on the wall. A fenced garden area lies in front, complemented by neatly arranged shrubs. A driveway leads to the entrance, enhancing accessibility.

Home in Amenia

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

4.98 out of 5 average rating, 132 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

4.88 out of 5 average rating, 222 reviews

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

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

4.99 out of 5 average rating, 141 reviews

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

Boulder Tree House

Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee 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 an exciting, romantic, unique experience but can accommodate a 3rd person.

The exterior view of the house is framed by overhanging tree branches with red leaves. A swing hangs from a nearby tree, and the stone fireplace is visible on the house's side. A spacious, grassy yard surrounds the home, creating an inviting setting.

4.97 out of 5 average rating, 112 reviews

Cozy house w/ screened porch near Kent & falls

Your family will be close to everything when you stay at this centrally-located place, 1 mile from Kent, CT. The house is cozy with a stone fireplace, wonderful screened in porch with skylights, two bedrooms, spacious living room with desk, full bath, back porch with fire-pit, grill and table and laundry in the basement. It's perfect for four but our dining room can convert to a spare bedroom as the door shuts and the table folds down. The kitchen is well stocked and we've cooked many meals

Superhost

A charming three-story farmhouse is surrounded by lush greenery, featuring a welcoming front porch with seating. The design includes a shingled exterior and a pathway leading to the entrance, all set against a backdrop of vibrant trees.

Home in Sharon

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

4.9 out of 5 average rating, 240 reviews

4.97 out of 5 average rating, 192 reviews

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!

5.0 out of 5 average rating, 49 reviews

Mountain Retreat with a View

A peaceful retreat less than two hours from NYC! Surrounded by protected parkland and an organic farm, our Fuller Mountain Retreat is a quiet, light-filled 3-bedroom, 2-bathroom oasis with gorgeous views and a wraparound deck. Nestled in a hidden nook near Macedonia Brook State Park, we're a short walk from the Pond Mountain Natural Area and just a 10-minute drive from Kent School, Marvelwood School, and all the amenities of the village of Kent.

4.92 out of 5 average rating, 309 reviews

Home in Cornwall

Tucked-away Charming Forest Cabin w/ Private Brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Superhost

A blue-brick exterior is complemented by a landscaped yard featuring two lounge chairs with light blue cushions. A dining area with an umbrella sits adjacent to the building, while stone pathways lead to the entrance flanked by greenery.

Home in Warren

Litchfield County Getaway

Welcome to Litchfield County! With only a 10 minute drive to Kent, and 20 to 25 minutes to the beautiful towns of Washington, Litchfield, Sharon, Roxbury, Cornwall, and Goshen, you will quickly realize the breathtaking beauty of Northwest CT. Surrounded by beautiful hikes, lakes, wineries, shops, galleries, and eateries, you wouldn't want to miss either spring or summer in this stunning corner of Connecticut.

4.93 out of 5 average rating, 118 reviews

4.97 out of 5 average rating, 268 reviews

The exterior of a spacious house is shown, featuring a light-colored facade and a neatly landscaped yard. A winding pathway leads to the entrance, surrounded by lush greenery and colorful flowers. A large window reflects the natural light filtering through the trees.

Home in Millerton

The House in a Beautiful Small Upstate Town

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

Popular amenities for Kent house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 213 reviews

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

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

4.81 out of 5 average rating, 136 reviews

4.99 out of 5 average rating, 279 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

4.94 out of 5 average rating, 401 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

4.88 out of 5 average rating, 243 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

5.0 out of 5 average rating, 191 reviews

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

4.93 out of 5 average rating, 126 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Chef’s Kitchen * Screened Porch * Near Woodstock

4.9 out of 5 average rating, 102 reviews

Home in Tannersville

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge

Weekly house rentals

The single-story home is surrounded by vibrant autumn foliage, with colorful trees framing the property. A spacious wooden deck extends from the house, providing outdoor seating. The lawn is expansive and well-maintained, inviting relaxation in the tranquil setting.

4.96 out of 5 average rating, 47 reviews

Country retreat on 4 private acres

A two-story yellow house features a classic entrance with a covered porch. Flanking the doorway are two large windows on each side, allowing for ample natural light. A pair of white adirondack chairs sits in front, and pumpkins adorn the steps, enhancing the welcoming feel.

4.96 out of 5 average rating, 71 reviews

Charming Home in Kent

5.0 out of 5 average rating, 92 reviews

The exterior of Millstone Manor is framed by lush greenery and mature trees. The home is characterized by a blend of siding and stone accents, featuring multiple windows and a welcoming entryway. A decorative gazebo with floral arrangements complements the inviting landscape.

Home in Dover Plains

Millstone Manor with East Mountain View

5.0 out of 5 average rating, 37 reviews

Home in Washington

Lago di Waramaugo! Lake Front Living

5.0 out of 5 average rating, 40 reviews

Home in Warren

Modern Timber Frame Colonial Saltbox

5.0 out of 5 average rating, 23 reviews

Home in Sharon

Nature lover’s retreat in NWCT

5.0 out of 5 average rating, 25 reviews

The House on High Meadow Farm

4.94 out of 5 average rating, 49 reviews

An open-concept living area features a modern teal sofa and a light gray lounge chair, both positioned on a textured area rug. Sunlight pours in through large windows, illuminating natural wood flooring and creating a bright and inviting space. A cozy wood stove is visible in the corner.

Home in Cornwall

Gunn Brook Mountain House

Private house rentals

5.0 out of 5 average rating, 34 reviews

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

Magical Woodland Getaway

5.0 out of 5 average rating, 49 reviews

The exterior of a large three-bedroom home is captured, showcasing a light-colored facade with multiple windows. A welcoming front porch with a double door entry is visible. The surrounding lush green lawn is accented by neatly trimmed shrubs and trees, contributing to a serene outdoor setting.

Home in Dover Plains

Somewhere That’s Green, Gameroom/Bar, Fenced yard

5.0 out of 5 average rating, 42 reviews

An open-concept living area is visible, featuring a spacious dining table with several chairs and a cozy seating area. Large windows allow natural light to illuminate the space, showcasing scenic views of the outdoors. Wooden beams and a fireplace add warmth to the inviting atmosphere.

Home in Stanfordville

Hilltop Hideaway- fire pit, hot tub, mountain view

4.9 out of 5 average rating, 72 reviews

Beautiful Barn w/ Pond Views. Pool/hot tub/sauna

5.0 out of 5 average rating, 23 reviews

Stunning Hillside Retreat Close to Kent

5.0 out of 5 average rating, 20 reviews

A charming two-story home showcases a blend of gray siding and natural stone accents. The front porch features white rocking chairs under a welcoming overhang. Large windows provide ample natural light, surrounded by well-maintained landscaping and trees in the background.

Home in Goshen

Northwest Connecticut Vacation House in Goshen

4.93 out of 5 average rating, 58 reviews

A light and airy living room features a large sectional sofa and a patterned rug underfoot. A stone fireplace is situated next to a stylish armchair, while artistic wall decor adds character. Large windows provide natural light and views of the surrounding landscape.

Home in Goshen

Halo Hollow Haus - Litchfield Lake & Ski Haven