We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Southbury

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Southbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

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

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest suite in Watertown

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!

Home in Woodbury

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."

Guest suite in Bethlehem

Breezy Crest private & restful w/antique charm

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 ski slopes.

Rental unit 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.

Guesthouse in Southbury

The Nest. Large studio in the Woods.

New large studio on secluded property at the end of the country road. Surrounded by trees and across the river from the National Audubon, bird sanctuary. 5 minutes from I-84. 4 minutes from town and 1 hour from Manhattan. Private, peaceful and restful. If you want to retreat to nature and rejuvenate your spirit this is the place for you. We look forward to hosting you in this lovely setting and sharing our favorite list of walking trails.

Rental unit in Southbury

Suite Hill studio

A private entrance to your studio located at the top of a hill. Surrounded by trees. Tranquility can be found. We are located near the Antique trail of Southbury. Its a 25 min ride to Danbury or 20 min ride to Waterbury. Just under 2 hours to NYC. And a little over 2 hours to Boston. We can provide a daily clean at an additional cost. They are grocery stores, TJ. Maxx and Starbucks within minutes.

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 private lounging/dining area. Separate entrance and parking space. 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 and just 10 minutes to Washington Depot.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Home in Southbury

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working (in progress) farm bordered by 155 acres of protected land trust with marked hiking trails. Southford Falls and Kettletown State Park are within minutes for fishing, picnicking, and hiking. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Southbury vacation rentals

Free parking on premises

Air conditioning

Stay near Southbury's top sights

Aquila's Nest Vineyards14 locals recommend

Blue Colony Diner7 locals recommend

Kettletown State Park11 locals recommend

Other great vacation rentals in Southbury

Cottage in Southbury

Sun Filled Cottage

Rental unit in Middlebury

Cozy Apartment with Water View of Brook

Rental unit in Waterbury

Funky downtown art studio apartment.

Cottage in Newtown

Private Country Cottage

Rental unit in Waterbury

Everything you need! Apartment!

Tiny home in Ansonia

Cozy Tiny Home for Solo Travelers Near Everything

Home in Waterbury

Come and enjoy the BURY's of CT!

Guest suite in Washington

Custom industrial farmhouse Apt in Washington Dpt

Quick stats about vacation rentals in Southbury

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.7K reviews
Nightly prices starting at
$20 before taxes and fees

Frequently Asked Questions

Do house rentals in Southbury have wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Southbury. Enjoy a tailored experience with all the comforts you desire.
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 house rentals in Southbury?
Experience the best of Southbury with our house 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.
Are there vacation rentals with a dedicated workspace in Southbury?
Yes! Work meets play with ease at over 10 vacation rentals in Southbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southbury?
Four-legged friends are welcome in Southbury. Choose from more than 10 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.

Destinations to explore