Photo by Chris Kailher

Southbury holiday lettings

We found 225 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Southbury that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Southbury

Showing deals for:14 Nov - 21 Nov

Image gallery for Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Terrace/patio
10 out of 10 rating
Exceptional
(20 reviews)

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury, CT

8% off
Price is £5,419
£774 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

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Find out more about Southbury

Find out more about Southbury

Head to the relaxing city of Southbury

The area's history and culture are just some of the reasons to come on holiday to Southbury. This relaxing city is known for its waterfalls, sporting events and cafes. A holiday 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 find attractions to see during your stay? Venture out of your cosy holiday rental 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 centre:

  • Quassy Amusement Park (4.6 mi / 7.5 km)
  • The Christmas Shop (10.8 mi / 17.5 km)
  • Great River Golf Club (15.7 mi / 25.3 km)
  • Richter Park Golf Course (16.5 mi / 26.5 km)
  • Hopkins Vineyard (17.2 mi / 27.7 km)
  • Lake Compounce (18.5 mi / 29.8 km)

Exploring the natural landscape of Southbury

Whether you're looking for adventure or just want to appreciate the scenery, Southbury is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Lillinonah (6.6 mi / 10.7 km)
  • Lake Zoar (8.1 mi / 13.1 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)

Transport to and around Southbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 3.9 mi (6.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to 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 when booking a holiday rental?
When considering a holiday rental in Southbury, Connecticut, the best area to stay in is the picturesque neighbourhood surrounding Lake Quassapaug. This charming area not only offers stunning lakeside views but also provides proximity to outdoor activities, making it a great choice for nature enthusiasts. You can enjoy kayaking or paddleboarding on the lake, or simply relax by the water's edge.

In addition to the scenic beauty, the neighbourhood is close to some delightful attractions, such as the Southbury Historical Society Museum, which offers insights into the local history, and the nearby Kettletown State Park, where you can explore hiking trails and enjoy a picnic amidst nature.
How much does it cost to rent a holiday home in Southbury?
Prices for holiday 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 holiday 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 holiday rental accomodation in Southbury?
In Southbury, a variety of holiday rentals are available, with apartments, holiday houses, and cottages all being quite popular. These rentals can be found in serene neighbourhoods that offer easy access to local parks and natural attractions. Most apartments typically feature modern amenities, including fully equipped kitchens, spacious living areas, and, in some cases, balconies for enjoying the picturesque surroundings. Holiday houses and cottages cater particularly well to families or groups, often providing multiple bedrooms, private outdoor spaces for relaxation, and facilities for barbecuing.
Are there any family house rentals in Southbury?
In Southbury, Connecticut, there are several family-friendly house rentals available. This charming town offers a mix of spacious homes that cater to families, with many located near local parks and recreational areas. Visitors can find properties featuring ample living spaces, full kitchens for preparing family meals, and outdoor areas superb for children to play.
Can I find long-stay holiday rentals in Southbury?
A long-stay holiday rental in Southbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Southbury?
In Southbury, there are several pet-friendly house rentals available, making it a suitable destination for travellers with furry companions. The area offers a variety of holiday homes that typically feature spacious layouts, fully equipped kitchens, and outdoor spaces such as gardens or patios, ideal for families or groups looking to relax and enjoy their stay.
Are there any remote work holiday rentals in Southbury?
In Southbury, Connecticut, there are several remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties are equipped with essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable chairs, providing a conducive environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Southbury holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Southbury with parking available—perfect for families or travellers 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 rental amenities include well-equipped kitchens, which typically come with essential cookware, dishware, and utensils, making it easy for guests to prepare their own meals. Many rentals also feature microwaves and ovens for added convenience, alongside refrigerators to keep food and drinks fresh.
When is the best time to visit Southbury for a holiday rental?
The best time to visit Southbury for a holiday rental is during the peak season from May to July. This period is particularly popular, as the warm weather invites outdoor enthusiasts to explore the picturesque landscapes and partake in various activities. With temperatures typically ranging from the mid-teens to low 30s Celsius, visitors can enjoy hiking, biking, and leisurely strolls through the charming town.

May stands out as a highlight, as it marks the start of vibrant spring blooms and community events. You'll find the local parks bustling with life, making it an ideal time for families and friends to gather and relish the outdoors. The longer days and pleasant climate also enhance your sightseeing options, with nearby attractions like the beautiful Southbury Training School grounds offering stunning scenery.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it presents a unique charm with festive decorations and a quieter atmosphere, great for those seeking a peaceful retreat. Enjoy cosy evenings by the fire after a day of exploring the winter landscape.
How early should I book a Southbury holiday rental?
Book your Southbury holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Southbury home rental booking on Vrbo?
To find Southbury holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Southbury holiday 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.

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