
House holiday rentals in Southbury
Find and book unique houses on Airbnb
Top-rated house rentals in Southbury
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

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."

WaterviewsTakeWedding pics,CollegeTours Yale&Beach
PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

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!

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.

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!

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.

Westshore Luxury
Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

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. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

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.

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.

Secluded modern forest cabin with 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
Popular amenities for house rentals in Southbury
House rentals with a pool

The Getaway-HOST & Co.

Hilltop House w/POOL/SPA- HOST & Co.

Redding Retreat with Pool

Midcentury Modern ZenHouse Sculptor Studio

Harlem Valley Hideout: Artsy ~ Pool ~ Tennis

Country retreat on 4 private acres

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Weekly house rentals

Cozy Nature Retreat at Chateau Madeux

Adorable Beach House on LI Sound

Modern Ranch style apartment.

Historic Hideaway - Spacious home - Lake Access

Private farm cottage +hiking

Mulberry Seaside Cottage

Cozy Cottage

New England Charm!
Private house rentals

The Seabreeze

Lakefront A-Frame Hudson Valley

Historic Designer City Getaway

Gunn Brook Mountain House

Candlewood Isle Cabin ~ Dog Friendly ~ Lake ~ Dock

Serenity by Lakefront Cottage!

Cozy cottage

The Art House: 5-Acre Getaway w/ Fireplace
Quick stats about house rentals in Southbury

Total holiday rentals
Explore 20 holiday rentals in Southbury

Nightly prices starting at
Southbury holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 910 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Southbury holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Southbury rentals

4.9 Average rating
Southbury stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with lake access Southbury
- Rentals with a fireplace Southbury
- Rentals with outdoor seating Southbury
- Rentals with a firepit Southbury
- Family-friendly rentals Southbury
- Rentals with a patio Southbury
- Pet-friendly rentals Southbury
- Rentals with a washing machine and dryer Southbury
- House rentals New Haven County
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- Yale University
- Fairfield Beach
- Six Flags New England
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Taconic State Park
- Mount Southington Ski Area
- Bear Mountain State Park
- Yale University Art Gallery
- Ski Sundown
- Sherwood Island State Park
- Sleeping Giant State Park
- Compo Beach
- Benmarl Winery
- Wesleyan University




