Vacation rentals with outdoor seating in Watertown

4.99 out of 5 average rating, 147 reviews

A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.

Cottage in Burlington

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

4.94 out of 5 average rating, 102 reviews

Cabin in Bethlehem

Cozy Cabin, Fireplace, Ski Nearby

Escape to Deer Ridge Cabin, a serene & cozy retreat designed to help you unwind. Relax by the warm glow of the fireplace or venture out to enjoy nearby skiing & tubing at Mohawk Mt. and Mt. Southington. Explore scenic hiking trails, indulge in local wineries, or visit Litchfield just 10 minutes away for fantastic dining & boutique shopping. Located only 2 hours from NYC, this peaceful cabin offers the perfect winter escape to nature while keeping you close to it all. Your perfect getaway awaits!

4.77 out of 5 average rating, 108 reviews

A two-story house with light blue siding is set against a backdrop of trees, showcasing green shutters on its windows. A stone pathway leads to the front door, with a well-maintained lawn and shrubs surrounding the home.

Home in Watertown

Guest House on Country Estate

In-town 2BR that sleeps 6 with fenced wooded yard, campfire, and room for a small pet. Kitchen with granite counters, essentials stocked. Spacious bedroom with queen and full bed, 2 TVs, full closets. Full bath, linens, AC, fireplace, Murphy bed, enterprise WiFi. Covered porch seats 6, gas BBQ. Laundry in basement. Weekly or summer monthly. Walk to town, 2 mins to Taft, near Rumsey, Gun, Westover. Quiet street with off-street parking. Great for visiting families, work stays, or summer getaways.

4.99 out of 5 average rating, 336 reviews

A textured chair with a unique design is positioned beside a small wooden table in a cozy living area. A patterned sofa, featuring geometric designs, adds warmth to the space, complemented by decorative wall plates and a subtle arrangement of flowers on a shelf.

Guest suite in Bethlehem

Quiet cottage w/chickens, gardens 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!

4.99 out of 5 average rating, 134 reviews

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

4.99 out of 5 average rating, 144 reviews

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!

4.99 out of 5 average rating, 432 reviews

A spacious room features a comfortable bed with a light blue quilt, complemented by decorative pillows. A desk and chair are positioned by a window, with bookshelves in the background. Natural light filters through the windows, creating a welcoming atmosphere.

Guest suite in Morris

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!

4.99 out of 5 average rating, 143 reviews

A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.

Home in Southbury

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

4.92 out of 5 average rating, 296 reviews

A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.

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.

4.97 out of 5 average rating, 314 reviews

A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.

Home in Bethlehem

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Guest suite in Wallingford

An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.

5 out of 5 average rating, 629 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

4.99 out of 5 average rating, 112 reviews

Apartment in Waterbury

Everything you need! Full Apartment!

Awesome bright 2nd floor apartment, has everything you need for your stay. Full Kitchen, Laundry and is in an very convenient and safe area. Walking distance to several restaurants and bars. Easy access to highway. Parking is available behind left garage, which may be available. Ask for details. Quiet area, On cul-de-sac. Wi-Fi, Netflix, Prime,Hulu FYI: I host a friendly card game every two weeks in the garage till 11:30 PM.

Popular amenities for Watertown outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.95 out of 5 average rating, 129 reviews

A panoramic view showcases vibrant autumn foliage across rolling hills, with colors ranging from deep reds to bright yellows. The scene is framed by lush greenery in the foreground, while rooftops and distant landscapes are visible in the background under a clear blue sky.

Home in Waterbury

Amazing views of the Brass City

4.93 out of 5 average rating, 121 reviews

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

4.91 out of 5 average rating, 100 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

4.99 out of 5 average rating, 125 reviews

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

Home in Collinsville

Best River View, on Rail Trail in Collinsville!

4.92 out of 5 average rating, 283 reviews

The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.

Home in Cornwall

Secluded modern forest cabin with private brook

4.9 out of 5 average rating, 115 reviews

A charming red homestead is surrounded by a light coating of snow, with a wooden staircase leading to the entrance. Leafless trees are visible in the foreground, and a convenience store can be seen in the background, enhancing the house's accessibility.

Home in Torrington

Charming Home in Litchfield County on a MAIN ROAD!

4.99 out of 5 average rating, 136 reviews

Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.

Home in Woodbury

Your Perfectly Wonderful Woodbury Sanctuary!

4.99 out of 5 average rating, 116 reviews

A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.

Home in Newtown

Comfortable home away from home- near everything

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 251 reviews

The property features a white two-story house with a covered front porch and lush green landscaping. A red barn stands nearby, contrasting against the blue sky, while a paved driveway leads up to the residence, offering ample space for off-street parking.

Apartment in Milford

Renovated Apartment in a Historic Farmhouse Estate

4.98 out of 5 average rating, 198 reviews

A compact kitchen area is shown, featuring white cabinetry and modern appliances. A round table with four black chairs, adorned with floral seat cushions, is set at the center. A small vase of fresh flowers adds a pop of color to the table.

Apartment in Torrington

Apartment on Main St.

4.84 out of 5 average rating, 120 reviews

The image captures a serene view of a clear pool reflecting the colorful sunset, framed by a meticulously paved patio. Two cabana beds are positioned next to the pool, with surrounding greenery and a decorative fence enhancing the outdoor space.

Apartment in Burlington

Charming apartment with breathtaking view!

4.98 out of 5 average rating, 125 reviews

A cozy living room features a spacious blue couch adorned with yellow accent pillows. A wooden coffee table is positioned in front, with colorful artwork hanging on the walls. A large flatscreen TV is mounted for entertainment, enhancing the comfort of the space.

Apartment in Westville

Retreat in New Haven by Stephanie and Damian

4.91 out of 5 average rating, 403 reviews

A bright and inviting living room features a floral-patterned couch and large windows adorned with green curtains. Decorative plant stands filled with various plants enhance the space, while a stained glass light fixture casts a warm glow over the area. A cozy atmosphere is created with soft lighting.

Apartment in Winsted

Gateway to the Berkshires

4.79 out of 5 average rating, 205 reviews

A comfortable living area features a leather sofa and two accent chairs beside a coffee table. Natural light fills the room through large windows adorned with sheer curtains. A ceiling fan enhances the airflow, while a neutral rug adds warmth to the space.

Apartment in New Britain

Comfort & Warmth Included: Your Escape, Reimagined

4.98 out of 5 average rating, 133 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.9 out of 5 average rating, 136 reviews

The entrance to the Joab Griffin House features a rich purple door framed by a white façade and classic architectural elements. Two potted plants flank the door, adding greenery to the entrance. An American flag gently waves nearby, enhancing the welcoming atmosphere.

Apartment in West Granby

Majestic Farmhouse Private & Peaceful Guest Apt.

Other vacation rentals with outdoor seating

4.98 out of 5 average rating, 247 reviews

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

4.92 out of 5 average rating, 36 reviews

The kitchen features modern cabinetry and appliances, including a microwave and a stove. A small dining table with two chairs sits in the center, topped with two placemats. Natural light filters through an adjacent area, creating an inviting cooking space.

Apartment in Watertown

Steele Brook Manor

4.95 out of 5 average rating, 133 reviews

A light-filled living room features a gray sectional sofa with a colorful throw pillow. A wooden console table stands beside a lamp, while natural light enters through two large windows adorned with white trim, providing views of the surrounding greenery. Vintage art pieces are displayed on the walls.

Guesthouse in Sharon

Cottage with a Waterfall View

4.87 out of 5 average rating, 229 reviews

The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.

Cottage in Granby

The Little Red Schoolhouse ~ Circa 1877

Farm stay in West Simsbury

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.

4.96 out of 5 average rating, 519 reviews

Flamig Farm Staycation

4.98 out of 5 average rating, 87 reviews

The historic home features a two-story structure with white siding and black shutters. A covered porch is highlighted at the front, surrounded by lush greenery and blooming flowers, set against a clear blue sky. A grassy lawn offers open space in the foreground.

Guest suite in Watertown

Private King suite w/ separate entry-Walk to Taft!

4.81 out of 5 average rating, 68 reviews

The exterior of the cottage features a light-colored facade with black shutters framing the windows. A stone garden bed with colorful flowers is visible along the walkway, leading to the entrance. Wooden steps ascend to the porch, surrounded by greenery from the surrounding trees.

Home in Watertown

Cozy Cottage