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

Your Perfectly Wonderful Woodbury Sanctuary!
Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. 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."

Lrg Studio Apartment - walk to Taft
Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Quintessential CT Town |Cozy Cottage |Pet Friendly
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.

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.

Quiet cottage w/chickens, gardens near Litchfield
Escape to this charming two-story 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, under 30 min to Mohawk and just 90 miles from NYC, you'll have easy access to winter fun!

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

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.

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.

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.

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.

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.

Cozy Apartment with Water View of Brook
Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.
Popular amenities for Southbury holiday rentals
Other great holiday rentals in Southbury

Fully Renovated Rural Barn

River Stone Hollow

Sun Filled Cottage

The Nest. Large studio in the Woods.

UNIQUE and GORGEOUS historic loft style rental

Custom industrial farmhouse Apt in Washington Dpt

Cozy Connecticut getaway!

A Lovely Cottage in the Woods
When is the best time to visit Southbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $248 NZD | $280 NZD | $235 NZD | $247 NZD | $280 NZD | $273 NZD | $250 NZD | $280 NZD | $278 NZD | $280 NZD | $232 NZD | $280 NZD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
Do house rentals in Southbury have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Southbury. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Southbury?
Experience the best of Southbury with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Southbury have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Southbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southbury have free parking?
Absolutely! We offer over 20 house rentals with free parking in Southbury. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Southbury?
Yes! Work meets play with ease at over 20 vacation rentals in Southbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Southbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Southbury. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Southbury?
Four-legged friends are welcome in Southbury. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Southbury?
Southbury has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Southbury

Total holiday rentals
Explore 50 holiday rentals in Southbury

Nightly prices starting at
Southbury holiday rentals start at $50 NZD per night before taxes and fees

Verified guest reviews
Over 2,440 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Southbury holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Southbury rentals

4.9 Average rating
Southbury stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a patio Southbury
- Pet-friendly rentals Southbury
- Rentals with lake access Southbury
- Rentals with outdoor seating Southbury
- House rentals Southbury
- Rentals with a washing machine and dryer Southbury
- Family-friendly rentals Southbury
- Rentals with a fire pit Southbury
- Rentals with a fireplace Southbury
- 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
- Long Island Aquarium
- Hammonasset Beach State Park
- Bear Mountain State Park
- Mount Southington Ski Area
- Taconic State Park
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- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Sleeping Giant State Park
- Ski Sundown
- Compo Beach
- Benmarl Winery
- Millbrook Vineyards & Winery




