House vacation rentals in Southbury

4.96 out of 5 average rating, 162 reviews

Home in Waterbury

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

4.98 out of 5 average rating, 179 reviews

A bright bedroom features two twin beds with white wood frames, positioned on either side of a decorative fireplace. A round wicker table sits at the center, adorned with a vase of flowers. Light streams in through multiple windows, creating a warm ambiance.

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

4.99 out of 5 average rating, 147 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!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this rambling, light-filled 2 story 4 bedroom 2.5 bath historic district home on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from popular restaurants and diners. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

4.95 out of 5 average rating, 107 reviews

A cozy living room features a stone fireplace with a mounted television above. Natural light enters through a large window, accented by sheer curtains. A plush rug covers the floor, surrounded by a sectional sofa and a chair, offering a comfortable gathering space.

Home in Waterbury

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

4.97 out of 5 average rating, 270 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

4.95 out of 5 average rating, 105 reviews

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.

4.93 out of 5 average rating, 132 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

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. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you! Note: Prices include 15.5% Airbnb service fee.

4.99 out of 5 average rating, 148 reviews

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

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.

4.98 out of 5 average rating, 176 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm, a one bedroom, one bath cottage located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. 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. **Access to the 2nd floor bedroom is a steep and open staircase** (see interior photo listed under Laundry)

4.94 out of 5 average rating, 143 reviews

Home in Danbury

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

4.98 out of 5 average rating, 336 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.

5.0 out of 5 average rating, 110 reviews

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.

Popular amenities for Southbury house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 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

4.88 out of 5 average rating, 130 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.96 out of 5 average rating, 270 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

4.97 out of 5 average rating, 38 reviews

A view through large windows, showcasing a serene lake surrounded by lush greenery. Outdoor seating is provided on the porch, inviting relaxation. The wooden ceiling complements the bright surroundings, enhancing the connection between indoor comforts and the tranquil lakefront landscape.

Home in New Milford

Bluewater Lodge | Pool, Dock, Fire Pit

5.0 out of 5 average rating, 21 reviews

A comfortable living area features a striped sofa adorned with patterned cushions, positioned beside a wooden coffee table. A vase of fresh flowers sits atop the table. Light filters through a large window with divided panes, illuminating the space and connecting to the kitchen area visible in the background.

Home in Sherman

Designers Historic Connecticut Home

5.0 out of 5 average rating, 28 reviews

A spacious living area features a brick fireplace at its center, surrounded by comfortable seating options. Light tones from the walls and furniture create a welcoming atmosphere. Large windows provide views of the outdoors, and a natural fiber rug adds texture to the floor.

Home in Litchfield

Litchfield Luxury Home w/Heated Pool

4.76 out of 5 average rating, 17 reviews

Colonial yellowhouse

Weekly house rentals

4.96 out of 5 average rating, 355 reviews

A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.

Home in Fairfield

Beautifully Restored Barn With New England Charm

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

4.99 out of 5 average rating, 124 reviews

Home in Fairfield

Renovated Cape Near beach, with Fire Pit and BBQ

5.0 out of 5 average rating, 20 reviews

Lakeside Sanctuary

The exterior of a blue house features multiple dormer windows and a red front door. A wooden deck extends along the front, with small shrubs planted on either side. The yard is grassy, surrounded by tall trees, contributing to a serene environment.

4.85 out of 5 average rating, 53 reviews

Cozy cute Relaxing home

The exterior of a two-story house is shown, featuring a unique architectural design with a sloped roof. Pillars support a large porch area, surrounded by lush greenery and trees. A car is parked in the driveway, and a few outdoor seating options can be seen.

4.88 out of 5 average rating, 68 reviews

Cozy Nature Retreat at Chateau Madeux

5.0 out of 5 average rating, 51 reviews

Charming 1875 Retreat - Walk to Village

A modern kitchen is shown with sleek white cabinetry and dark granite countertops. A spacious island with bar stools is positioned in the center, complemented by stainless steel appliances. Natural light is provided through large windows, illuminating the warm wooden flooring.

4.94 out of 5 average rating, 62 reviews

Sunset Living

Private house rentals

4.97 out of 5 average rating, 79 reviews

A tranquil view of Swan Lake is captured, surrounded by autumn foliage. Colorful outdoor chairs are positioned on a leaf-covered shore. Sunlight reflects off the calm water, creating a serene atmosphere that invites relaxation.

Home in Oxford

Lakefront Summer Oasis - kayak, fish and get cozy!

4.9 out of 5 average rating, 60 reviews

The exterior of a two-story Connecticut country house is presented, featuring light blue siding and white trim. Lush green grass surrounds the home, complemented by ornamental grasses. Large windows reflect natural light, enhancing the charming appearance of this inviting property surrounded by trees.

Home in Woodbury

Renovated Connecticut Country House sleeps 14!

4.96 out of 5 average rating, 23 reviews

An open-plan living area is showcased, featuring a brick fireplace as a focal point. Skylights allow natural light to fill the space. Comfortable seating includes a plush tufted ottoman and two armchairs, enhancing the cozy atmosphere of the room.

Home in Bethlehem

Nature’s Nest: Cozy Woodland Escape for Friends

5.0 out of 5 average rating, 56 reviews

An outdoor patio area features comfortable seating with wicker chairs and a glass-top table, shaded by an awning. Lush greenery and the serene water of Candlewood Lake are visible in the background, completing the tranquil setting.

Home in Danbury

Candlewood Lake - Lakefront Family Getaway 3775sqf

A grand Victorian house with a yellow exterior features multiple gabled roofs and large windows. A spacious front porch adorned with white railings is visible, along with well-maintained landscaping that includes green grass and trees. The structure showcases classic architectural details.

4.81 out of 5 average rating, 16 reviews

Scudder-Smith House

A porch area features three adirondack chairs in green and white, arranged for relaxation. A small side table is present alongside a beige mat. Natural light filters through large windows, offering a glimpse of the serene yard beyond.

4.97 out of 5 average rating, 78 reviews

Charming Relaxing Raised Ranch

4.65 out of 5 average rating, 98 reviews

The exterior of the house is showcased, featuring a wooden deck supported by sturdy pillars. Large windows provide a view into the living space. Surrounding greenery includes trees and a lawn, creating a natural setting with a kayak resting under the deck.

Home in Oxford

Lakefront Getaway