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Southbury vacation rentals

We found 235 vacation rentals — enter your dates for availability

Discover a selection of 7 apartments and other vacation rentals in Southbury that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include parking and a pool. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Southbury

Showing deals for:May 29 - Jun 5

Image gallery for Nature & Luxury @Lavender Lake Est (Kosher optional)

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

9% off
Price is $2,326
$16,282 for 7 nights
All fees included
Nature & Luxury @Lavender Lake Est (Kosher optional)

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Find out more about Southbury

Why visit Southbury

  • Outdoor Adventures: Southbury boasts beautiful national and state parks, perfect for hiking, fishing, and enjoying nature.
  • Scenic Settlers Park: Relax and unwind in Settlers Park, known for its picturesque views and serene atmosphere.
  • Charming South Main Street: Stroll along South Main Street, featuring delightful shops and local eateries.
  • Family-Friendly Activities: The area offers numerous activities suitable for families, ensuring fun for all ages.
  • Cozy Accommodations: Choose from charming cottages and modern apartments for a comfortable stay.

Popular types of accommodation in Southbury

If you're exploring vacation rentals in Southbury, you're in for a treat. The most popular accommodations include houses, cozy cottages, and modern apartments. Whether you're seeking a spacious apartment in Southbury or a charming cottage to unwind, we have options tailored to your needs. Discover the perfect Southbury rentals that offer the comfort and convenience you desire for your getaway.

  • Houses: This popular choice offers spacious living, perfect for families or groups looking to relax together in comfort.
  • Cottages: These quaint and cozy accommodations provide a charming atmosphere for a peaceful getaway, ideal for couples or solo travelers.
  • Apartments: A convenient option for those who prefer a home-like feel, offering all the amenities needed for a comfortable stay.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats offer a unique experience in a serene setting.
  • Condos: Great for travelers seeking modern amenities and a community vibe, providing a blend of comfort and convenience.**

Top attractions near Southbury

Southbury, Connecticut, offers a perfect blend of outdoor adventure, romance, and family-friendly activities. Visitors can explore beautiful national and state parks, serene lakes, and vibrant urban parks. The area's attractions cater to those seeking outdoor experiences, cultural enrichment, and picturesque scenery, ensuring a memorable vacation for everyone.

  • Quassy Amusement Park: Located 5 miles from Southbury, Quassy Amusement Park offers a fun-filled experience with thrilling rides, water attractions, and family-friendly entertainment. Its outdoor setting is perfect for adventure seekers and families looking to make lasting memories.
  • Candlewood Lake: Situated 12 miles away, Candlewood Lake boasts beautiful beaches and stunning scenery, making it an ideal spot for romance and relaxation. Enjoy swimming, picnicking, or simply soaking in the picturesque views.
  • Southford Falls State Park: Just 3 miles from Southbury, Southford Falls State Park features hiking trails and breathtaking waterfalls. It's a great destination for outdoor enthusiasts seeking adventure and natural beauty.

Things to do recommended for couples

Looking for a romantic getaway in Southbury? Indulge in a wine tasting at DiGrazia Winery, hit the slopes at Woodbury Ski Area, or enjoy an adventurous day of waterskiing at Waterski Connecticut. Each experience offers a perfect blend of romance and excitement for couples.

Things to do recommended for families

Your family will love exploring Kettletown State Park, a relaxing recreational area just 4 miles from Southbury, perfect for picnics and nature walks. For more fun, visit the SportsCenter of Connecticut, located 16 miles away, offering various activities for everyone to enjoy.

Things to do recommended for groups

Explore the Elephant's Trunk Flea Market for unique finds and local flair, just 11 miles away. Enjoy family-friendly shopping and entertainment at Pilgrim Mall, only 4 miles from Southbury. For a cultural evening, catch a show at the Palace Theatre, located 10 miles from town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Southbury

If you're traveling with a group, with family, bringing pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Southbury with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Southbury with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with having suitable amenities like a private pool. Additionally, think about how close you'll be to attractions that are great for families.
  • Taking your pets with you to Southbury: For many families, a vacation wouldn’t be the same without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Southbury: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Southbury

Southbury, Connecticut, offers a delightful blend of outdoor adventures and rich history, perfect for family-friendly or romantic getaways. Explore the scenic Settlers Park for relaxation, stroll along South Main Street for charming shops and eateries, and unwind in neighborhoods boasting large yards and welcoming vibes. Just a short drive away, you'll find friendly communities that enhance your travel experience with their historic charm and inviting atmosphere. A visit to Southbury promises memorable moments for every traveler.

  • Danbury: Located 14 miles from Southbury, Danbury is a vibrant city known for its scenic beauty and outdoor activities. Visitors can enjoy a romantic stroll around Candlewood Lake or explore the picturesque parks scattered throughout the area. Danbury also offers a variety of shopping options, including the Danbury Fair Mall, which is perfect for a leisurely day of retail therapy. With its blend of educational venues and event spaces, Danbury serves as an excellent base for both relaxation and adventure.
  • Waterbury: Just 10 miles from Southbury, Waterbury is a family-friendly destination offering a range of outdoor adventures. The city's attractions include the popular Quassy Amusement Park and Waterbury's own waterpark, making it a great spot for families looking for fun and excitement. Waterbury also features educational opportunities and resorts, providing visitors with various choices for leisure and learning. With its rich history and engaging activities, Waterbury promises an adventurous getaway for all ages.
  • Woodbury: A mere 5 miles from Southbury, Woodbury is perfect for those seeking a blend of outdoor experiences and romantic scenery. This charming city is home to beautiful ski fields and lovely shopping centers, catering to both adventure seekers and casual shoppers. Nature enthusiasts will appreciate the nearby state parks and lakes, offering opportunities for hiking, fishing, and peaceful picnics. With its quaint atmosphere and stunning landscapes, Woodbury is an ideal destination for a serene and picturesque retreat.

Best time to go to Southbury

If you're planning a trip to Southbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.2°F (-2.1°C)Light RainMostly SunnyAverageSlightly Low
February29.8°F (-1.2°C)Light RainMostly CloudyAverageAverage
March36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
April47.8°F (8.8°C)Light RainMostly SunnySlightly HighSlightly Low
May58.3°F (14.6°C)Light RainMostly SunnySlightly HighAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August71.6°F (22.0°C)Light RainMostly SunnyAverageSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
October54.1°F (12.3°C)Light RainMostly SunnySlightly LowAverage
November42.4°F (5.8°C)Light RainMostly SunnySlightly LowAverage
December34.5°F (1.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to cut costs on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. You might also discover that extending your stay can lead to significant savings. To help you find the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on your entire booking. Being the organizer truly has its rewards. When you enroll in our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a dedicated area to plan your next adventures, pick up right where you left off, or review and arrange your travel plans. You can easily access the properties you’ve saved and booked in your Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the tranquil city of Southbury

The area's history and culture are just a few of the reasons to vacation in Southbury. This relaxing city is known for its waterfalls, sporting events and cafes. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Southbury

Do you want to discover attractions to see while you're in the area? Venture out of your vacation home and experience everything that Southbury has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Quassy Amusement Park (4.6 mi / 7.5 km)
  • Great River Golf Club (15.7 mi / 25.3 km)
  • Mount Southington Ski Area (16.5 mi / 26.6 km)
  • Hopkins Vineyard (17.2 mi / 27.7 km)
  • Lake Compounce (18.5 mi / 29.8 km)
  • Beardsley Zoo (18.6 mi / 29.9 km)

Exploring the natural landscape of Southbury

Whether you're an outdoor enthusiast or just want to take in the scenery, Southbury is a great place to spend some time outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Beacon Falls Town Recreation Field (7.5 mi / 12.1 km)
  • Bellamy-Ferriday House and Garden (11.1 mi / 17.9 km)
  • Steep Rock Preserve (11.4 mi / 18.4 km)
  • Candlewood Lake (12.3 mi / 19.8 km)
  • Bear Mountain Reservation (12.9 mi / 20.7 km)
  • Rogers Park (13.4 mi / 21.6 km)

Transportation to and around Southbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 3.9 mi (6.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Danbury, CT (DXR-Danbury Municipal), which is 15.9 mi (25.6 km) away.

Frequently asked questions

What is the best area to stay in Southbury, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Southbury, Connecticut, a popular area to stay is near the charming downtown district. This area offers a delightful blend of local shops, cafes, and restaurants, making it a convenient and vibrant spot for visitors. Here, you'll find several properties that cater to various tastes and budgets, providing a comfortable home base for your stay.

Another appealing neighborhood is the area surrounding Southbury's scenic parks and nature trails. This region is superb for outdoor enthusiasts, as it features beautiful landscapes and opportunities for hiking and picnicking. Additionally, the nearby Lake Quassapaug is a popular attraction, offering recreational activities such as swimming, boating, and fishing, making it a great choice for families and nature lovers alike.
How much does it cost to rent a vacation home in Southbury?
Prices for vacation rentals in Southbury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Southbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Southbury vacation house rentals?
You can find great discounts on house rentals in Southbury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Southbury?
In Southbury, vacation houses are the most common type of rental, with several options available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them suitable for families or groups seeking a comfortable stay. Many of these houses come with outdoor areas, such as patios or gardens, superb for enjoying the natural surroundings. Additionally, there are several apartments and cottages available, offering cozy alternatives for those looking for a more intimate setting.
Are there any family house rentals in Southbury?
In Southbury, Connecticut, there are several family-friendly house rentals available, offering a welcoming retreat for visitors. Properties in this area typically feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play and families can gather. Many homes come with amenities such as Wi-Fi, air conditioning, and sometimes even game rooms or basements for entertainment.

Situated in the beautiful Litchfield Hills region, Southbury is close to various attractions. Families can enjoy activities at nearby parks, including the scenic Lake Quassapaug, where swimming and picnicking are popular. The town also has charming shops and restaurants that provide a taste of local culture.
Can I rent a vacation home with a pool or hot tub in Southbury?
In Southbury, Connecticut, travelers can find several vacation homes available for rent that feature pools and hot tubs. This charming town, set amidst picturesque landscapes, offers a variety of properties in serene neighborhoods, great for a relaxing getaway. Many of these rentals come equipped with private pools, hot tubs, and outdoor spaces ideal for enjoying the scenic views. Additionally, travelers can expect amenities such as fully equipped kitchens, spacious living areas, and comfortable bedrooms, suiting both relaxation and entertainment needs.
Can I find long-stay vacation rentals in Southbury?
A long-stay vacation rental in Southbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Southbury?
In Southbury, Connecticut, there are several options for remote work vacation rentals, with around 12 properties available. Travelers can expect accommodations equipped with essential amenities for working remotely, such as free Wi-Fi, comfortable workspaces, and reliable internet connections. Many of these rentals may also offer additional features like spacious living areas, full kitchens for convenient meal preparation, and outdoor spaces to relax and recharge during breaks.

The area is known for its picturesque landscapes, including lakes and parks, providing a serene backdrop for those balancing work and leisure. Nearby attractions like the Southbury Training School and the beautiful Lake Zoar offer opportunities for outdoor activities and exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Southbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Southbury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Southbury?
In Southbury, popular vacation rental amenities include kitchens, which allow guests to prepare their own meals, as well as onsite parking for convenience. Many rentals also provide coffee and tea makers, ensuring that travelers can enjoy their morning brews at their leisure. Additionally, many properties are pet-friendly, permitting guests to bring their furry companions along, and service animals are also welcomed.
When is the best time to visit Southbury for a vacation rental?
The best time to book a vacation rental in Southbury is during the peak season from May to July. This vibrant period welcomes travelers eager to enjoy the lush landscapes and outdoor activities that the region has to offer. May, in particular, is a standout month, as the weather begins to warm up, with temperatures typically ranging from the mid-50s to mid-70s Fahrenheit, superb for hiking and exploring the scenic beauty of the area.

During these months, you can partake in a variety of activities, from visiting local parks to enjoying the charming downtown area filled with shops and eateries. The warm weather invites you to relish outdoor picnics or take leisurely strolls along the picturesque Lake Zoar, which is ideal for kayaking or fishing.

For those seeking a more budget-friendly option, consider visiting Southbury in December. While this month is quieter, it offers a unique charm with holiday festivities and the opportunity to experience the winter landscape, creating a serene atmosphere superb for cozying up in your rental.
How early should I book a Southbury vacation rental?
Book your Southbury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Southbury, Connecticut, United States of America?
In Southbury, visitors can enjoy a variety of attractions that highlight the area's natural beauty and history. The Southbury Green is a central hub with shopping and dining options, making it a convenient starting point for exploring the town. For outdoor enthusiasts, Lake Quassapaug offers opportunities for swimming, fishing, and picnicking, with surrounding parks providing trails for hiking and biking.

Nearby, the historic Southbury Town Hall and the Old Town Hall Museum offer insights into the local history and culture. Additionally, the Pomperaug River provides scenic views and is great for leisurely walks. For a taste of the arts, the Southbury Community Theatre hosts various performances throughout the year, showcasing local talent.
Can I change or cancel my Southbury home rental booking on Vrbo?
To find Southbury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Southbury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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