Southbury holiday rentals

We found 253 holiday rentals — enter your dates for availability
Discover a selection of 8 apartments 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:25 Dec - 1 Jan

Private kitchen
Living area
Dining
Balcony
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
AU$12,360
for 7 nights, 1 home
AU$1,766 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Foyer
Sunset
Living Room
Kitchen
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

5% off
AU$18,661
for 7 nights, 1 home
AU$2,666 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
18' x 36' heated pool.
Gorgeous sunsets every night
Steam shower
Private kitchen
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$13,175
for 7 nights, 1 home
AU$1,882 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Family room by night with garage doors retracted.
Outdoor dining
Well stocked eat-in kitchen with stainless appliances.
Private kitchen
Exceptional
(122 reviews)

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Danbury

8% off
AU$5,852
for 7 nights, 1 home
AU$836 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Entrance
Summer; forest view
Winter; main room
Kitchen
Exceptional
(8 reviews)

Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes

Waterbury

8% off
AU$4,075
for 7 nights, 1 cabin
AU$582 per night
includes taxes & fees
Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes
View from property
Flat yard,
double fridge for extea space
Living area
Exceptional
(87 reviews)

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

New Fairfield

8% off
AU$18,804
for 7 nights, 1 home
AU$2,686 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Property grounds
Interior
Exterior
Property grounds
Exceptional
(35 reviews)

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

Danbury

8% off
AU$10,908
for 7 nights, 1 home
AU$1,558 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Interior
small, covered front porch on cottage
Lovely rolling 8 Acre farmland is shared with the main house
New refrigerator, microwave, air fryer, coffee maker 2022
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$3,577
for 7 nights, 1 cottage
AU$511 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Private kitchen
Private kitchen
Interior
Room
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,150
for 7 nights, 1 home
AU$307 per night
includes taxes & fees
Excellent Home Away From Home
Living area
Property grounds
Terrace/patio
Private kitchen
Exceptional
(15 reviews)

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown

8% off
AU$2,098
for 7 nights, 1 cottage
AU$300 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Bathroom
View of the Pond
Living Room
Entryway Stairs
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,384
for 7 nights, 1 apartment
AU$341 per night
includes taxes & fees
Private Apartment in Southbury 101
Interior
Living area
Interior
Bathroom
Exceptional
(37 reviews)

1 bedroom Cozy, comfy, super clean, great location and own entrance!!

Shelton

7% off
AU$794
for 7 nights, 1 apartment
AU$113 per night
includes taxes & fees
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Outdoors
Open Concept Living Room, Dining Room, Kitchen
Dining Room
Queen Bedroom
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$2,169
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Private Apartment in Southbury 102

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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 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)
  • Beacon Falls Town Recreation Field (7.5 mi / 12.1 km)
  • Waterbury Green (10.4 mi / 16.7 km)
  • Steep Rock Preserve (11.4 mi / 18.4 km)
  • Candlewood Lake (12.3 mi / 19.8 km)
  • Tarrywile Park and Mansion (14.2 mi / 22.8 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 area around the town centre is particularly appealing. This neighbourhood offers a charming mix of convenience and local character, making it a great base for your stay. Here, you'll find a selection of properties that cater to various preferences, from cosy cottages to more spacious family homes.One of the top attractions in the vicinity is Lake Quassapaug, which is great for outdoor enthusiasts. This lovely lake is a great spot for swimming, kayaking, and fishing, providing a picturesque setting for relaxation. Additionally, the nearby Southbury Training School, while primarily a historical site, showcases the area's rich heritage and offers a unique glimpse into the past.For those interested in local culture, the Southbury Public Library often hosts events and activities, making it a vibrant community hub.
What is the most popular type of holiday rental accomodation in Southbury?
In Southbury, apartments are the most prevalent type of holiday rental, with around 28 options available across the area. These apartments typically provide a comfortable living space, complete with fully equipped kitchens, cosy living areas, and often convenient access to local amenities. This makes them ideal for both short and extended stays.Additionally, there are approximately 16 holiday houses available, which cater to families or larger groups seeking more space. These houses generally feature multiple bedrooms, outdoor areas for relaxation, and full kitchens, enabling guests to enjoy a homely atmosphere. Furthermore, several cottages can be found in the area, offering a quaint and charming experience, often located in more tranquil settings.
Are there any family house rentals in Southbury?
In Southbury, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for those looking to accommodate the whole family. Many of these homes are situated in tranquil neighbourhoods that offer spacious living areas, allowing for comfortable family gatherings. Visitors can expect amenities such as fully equipped kitchens, great for preparing meals together, as well as outdoor spaces where children can play and families can enjoy barbecues.The local area is rich in natural beauty, with nearby attractions like Lake Zoar providing opportunities for hiking, fishing, and picnicking. Families can also explore the charming downtown, which features quaint shops and local eateries.
Can I rent a holiday home with a pool or hot tub in Southbury?
In Southbury, there are several holiday homes available for rent that feature pools and hot tubs. This charming town in Connecticut offers a picturesque setting with access to outdoor activities and local attractions. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas, great for relaxation after a day of exploring. Inside, travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and modern conveniences like Wi-Fi and air conditioning.
Are there pet-friendly house rentals in Southbury?
In Southbury, there are several pet-friendly house rentals available, providing a comfortable and welcoming environment for both travellers and their furry companions. Many of these holiday homes feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, superb for families or groups.The area is surrounded by beautiful natural landscapes, including parks and recreational areas where pets can enjoy outdoor activities. For instance, Southbury's parks often have trails suitable for walking dogs, and the nearby Lake Zoar offers opportunities for water activities and scenic views.
Are there any remote work holiday rentals in Southbury?
In Southbury, Connecticut, there are numerous remote work-friendly holiday rentals available, with around 48 options to choose from. This charming town offers a peaceful environment ideal for those looking to balance work and relaxation. Many of the properties come equipped with high-speed internet and Wi-Fi, ensuring a reliable connection for remote work. Additionally, you can expect amenities such as dedicated workspaces with desks and ergonomic chairs, allowing for a comfortable working environment.The area is surrounded by natural beauty, with opportunities for outdoor activities like hiking and exploring nearby parks. Southbury also features local shops and dining options, providing convenient access to essentials during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Southbury?
In Southbury, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many properties also feature coffee and tea makers, ensuring that travellers can enjoy a warm beverage at their leisure. Additionally, some rentals are pet-friendly, permitting guests to bring their furry companions along, and service animals are welcomed as well.
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 among travellers seeking to enjoy the beautiful spring and summer weather, great for outdoor activities and family gatherings.In May, you can expect pleasant temperatures ranging from 10 to 25 degrees Celsius, making it ideal for exploring Southbury's picturesque parks and scenic walking trails. The lush greenery and blooming flowers create a stunning backdrop for sightseeing and leisurely strolls. Outdoor events often take place during this time, adding to the vibrant setting in the town.If you're looking for a quieter experience with potential savings, consider a visit in December. While this is the low season, the charming winter scenery and festive decorations around the holidays can provide a unique and cosy atmosphere for your stay. You can enjoy the local festivities and perhaps indulge in some winter sports or indoor activities.Ultimately, the best time for your holiday rental in Southbury will depend on whether you prefer the lively summer atmosphere filled with outdoor fun or the serene beauty of winter.
What are the top attractions in Southbury?
In Southbury, visitors can enjoy a mix of natural beauty and local charm. One of the top attractions is Lake Quassapaug, which offers opportunities for swimming, fishing, and picnicking along its scenic shores. The nearby Southbury Historical Society provides insight into the area's rich history, featuring exhibits and events that celebrate local heritage.For outdoor enthusiasts, the Southbury Parks and Recreation Department manages several parks and trails, including the expansive Ballantine Park, which features walking paths, sports facilities, and playgrounds, making it ideal for families. Additionally, the town is close to the Pomperaug River, where visitors can enjoy kayaking and canoeing.For a bit of culture, the Southbury Community Theatre often hosts local performances and events, providing a glimpse into the area's artistic community.
Are all fees included in the Southbury holiday homes prices shown on Stayz?
Stayz 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.
Are there any Southbury holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Southbury holiday homes?
You can find great discounts on holiday homes in Southbury on Stayz, 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.
Can I change or cancel my Southbury holiday home booking on Stayz?
To find Southbury holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Southbury?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Southbury holiday home?
Book your Southbury holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Southbury?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Southbury to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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