Woodbury holiday rentals

We found 236 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Woodbury that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Woodbury

Showing deals for:1 Jan - 8 Jan

Bedroom 1: King
Sunset
Kitchen
Living Room
Exceptional
(10 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
AU$18,109
for 7 nights, 1 home
AU$2,587 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Steam shower
Gorgeous sunsets every night
Private kitchen
18' x 36' heated pool.
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$11,844
for 7 nights, 1 home
AU$1,692 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
3rd sleeping area with ground-floor walkout
Summer; forest view
Winter; main room
Kitchen
Exceptional
(8 reviews)

Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes

Waterbury

8% off
AU$4,127
for 7 nights, 1 cabin
AU$590 per night
includes taxes & fees
Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes
Relax with your morning coffee or a glass of wine on our private back patio.
Large open kitchen & dining area has lots of comfortable seating.
Large dining table has plenty of space for our guests.
Easy access to the jungle gym & backyard from the lower level.
Exceptional
(21 reviews)

Bantam Beauty - Surrounded By Nature!

Bantam

8% off
AU$7,007
for 7 nights, 1 home
AU$1,001 per night
includes taxes & fees
Bantam Beauty - Surrounded By Nature!
Exterior
Interior
Outdoor dining
Interior
Exceptional
(52 reviews)

Beach, Paddle Boards. Swim

Bethlehem

7% off
AU$2,503
for 7 nights, 1 cabin
AU$358 per night
includes taxes & fees
Beach, Paddle Boards. Swim
Interior
Exterior
Room
Barn Style Home - Best Location! Views!
Exceptional
(7 reviews)

"Kielwasser 5BR" 2Hrs NYC,Best Town,Restaurants! HeatedPool,BBQ,4FPs, PoshPadsCT

Washington Depot

35% off
AU$10,150
for 7 nights, 1 home
AU$1,450 per night
includes taxes & fees
"Kielwasser 5BR" 2Hrs NYC,Best Town,Restaurants! HeatedPool,BBQ,4FPs, PoshPadsCT
Interior
small, covered front porch on cottage
Front of Cottage 2024
Lovely rolling 8 Acre farmland is shared with the main house
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$2,157
for 7 nights, 1 cottage
AU$308 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Terrace/patio
Living room
Dining
Exterior
Exceptional
(8 reviews)

Beautiful antique gem- The oldest house in Litchfield CT

Litchfield

12% off
AU$4,891
for 7 nights, 1 cottage
AU$699 per night
includes taxes & fees
Beautiful antique gem- The oldest house in Litchfield CT
Private kitchen
Private kitchen
Dining
Interior
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,180
for 7 nights, 1 home
AU$311 per night
includes taxes & fees
Excellent Home Away From Home
Living room
Exterior
Private kitchen
Interior
Exceptional
(19 reviews)

Barn Apartment Hideaway

Washington Depot

15% off
AU$2,947
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
Barn Apartment Hideaway
Exterior
Property grounds
Terrace/patio
Living area
Exceptional
(16 reviews)

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

Watertown

8% off
AU$2,127
for 7 nights, 1 cottage
AU$304 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Private kitchen
Property grounds
Room
Living area
Exceptional
(8 reviews)

Spacious Lakeside Hideaway

Newtown

8% off
AU$2,276
for 7 nights, 1 apartment
AU$325 per night
includes taxes & fees
Spacious Lakeside Hideaway
Kitchen
View of the Pond
Living Room
Bathroom
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,112
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
Private Apartment in Southbury 101
Living area
Interior
Private kitchen
Exterior
Exceptional
(5 reviews)

The Perch in the Purchase -- Cozy, unique, and private

Southbury

8% off
AU$1,730
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
The Perch in the Purchase -- Cozy, unique, and private
Queen Bedroom
Open Concept Living Room, Dining Room, Kitchen
Outdoors
Open Concept Living Room and Kitchen
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

7% off
AU$1,927
for 7 nights, 1 apartment
AU$275 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

Historical Woodbury will entice you

Enjoy the history and other features of Woodbury. This walkable city is known for its hiking, skiing and coffee shops. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Woodbury

Are you looking for top things to see and do in the area? Venture out of your holiday home and check out everything that makes Woodbury a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Quassy Amusement Park (3.3 mi / 5.3 km)
  • The Christmas Shop (6.3 mi / 10.2 km)
  • Hopkins Vineyard (13.4 mi / 21.5 km)
  • Mount Southington Ski Area (14.9 mi / 24 km)
  • Lake Compounce (16 mi / 25.8 km)
  • Connecticut Valley Winery (20.6 mi / 33.2 km)

Exploring the natural landscape of Woodbury

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Woodbury is a great place to spend some time outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Lake Lillinonah (8 mi / 12.9 km)
  • Waterbury Green (8.7 mi / 14 km)
  • Beacon Falls Town Recreation Field (9.8 mi / 15.8 km)
  • Bantam Lake (11.1 mi / 17.8 km)
  • White Memorial Conservation Center (12.4 mi / 20 km)
  • Candlewood Lake (13 mi / 20.9 km)

Travelling to and around Woodbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 5.8 mi (9.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 18.6 mi (30 km) away.

Frequently asked questions

What is the best area to stay in Woodbury when booking a holiday rental?
When considering a holiday rental in Woodbury, Connecticut, a popular area to stay in is the charming town centre, which offers a delightful blend of quaint shops and local eateries. This area is particularly appealing for those who appreciate a small-town atmosphere with easy access to nature. The nearby Woodbury Common, a scenic area for outdoor activities, is superb for hiking and enjoying the natural beauty of Connecticut.Another excellent option is the residential neighbourhoods slightly further out of the town centre, where you can find larger properties that offer privacy and tranquility. These areas are close to attractions such as the historic Glebe House Museum and the serene Lake Quassapaug, providing opportunities for both cultural exploration and leisure activities.Woodbury is known for its picturesque landscape and rich history, making it an inviting destination for holidaymakers.
What is the most popular type of holiday rental accomodation in Woodbury?
In Woodbury, holiday houses are the most popular type of holiday rental, with around 24 available in the area. These properties are typically situated in tranquil neighbourhoods, offering a peaceful retreat for visitors. Most holiday houses come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces for relaxation or alfresco dining.In addition to holiday houses, there are several cottages and cabins available, which provide a more rustic charm. These options often feature cosy interiors, fireplaces, and proximity to Woodbury's scenic spots, making them ideal for nature lovers or those looking for a quiet getaway.
Are there any family house rentals in Woodbury?
In Woodbury, Connecticut, there are several family-friendly house rentals available, making it a lovely destination for groups seeking a retreat. The area is known for its serene landscapes and charming New England atmosphere, with properties often featuring spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.Visitors will appreciate the proximity to local parks and recreational activities, such as hiking trails and scenic spots great for picnics. The town's quaint centre offers a selection of shops and eateries, adding to the overall charm of the locale.
Can I rent a holiday home with a pool or hot tub in Woodbury?
In Woodbury, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque town is known for its scenic landscapes and charming New England atmosphere, making it an appealing destination for a relaxing getaway. Many of the properties come equipped with amenities such as private swimming pools, hot tubs, spacious outdoor areas for barbecues, and fully outfitted kitchens, superb for families or groups looking to enjoy their time together.
Are there pet-friendly house rentals in Woodbury?
In Woodbury, Connecticut, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. The area features charming homes that often come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, great for families or groups. Many properties also provide additional conveniences like laundry facilities and outdoor spaces for pets to enjoy.Woodbury is known for its picturesque scenery and outdoor activities, with nearby parks and trails that are ideal for walks with your furry companions. The town's natural beauty, combined with the comfort of pet-friendly accommodations, ensures a pleasant stay for both you and your pet.
Are there any remote work holiday rentals in Woodbury?
In Woodbury, Connecticut, there are numerous options for remote work holiday rentals, with around 36 available in the area. Many of these properties are equipped with essential amenities to ensure a productive stay, such as free Wi-Fi in both public areas and individual rooms, as well as dedicated desk spaces for working comfortably.Travellers can expect a range of accommodation types, from cosy cottages to spacious homes, often featuring modern comforts like fully equipped kitchens and outdoor spaces for relaxation after a long day of work. The scenic surroundings of Woodbury, with its charming rural backdrop and proximity to local attractions, provide a pleasant environment for remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Woodbury?
In Woodbury, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, enhancing the home-like experience. Many rentals also feature fireplaces, providing a cosy atmosphere, particularly during colder months. Outdoor spaces such as decks or patios are common, offering a lovely spot for relaxation or dining al fresco. Additionally, some properties have dedicated workspaces or desks, suiting those who may need to catch up on work while enjoying their stay.
When is the best time to visit Woodbury for a holiday rental?
The peak travel season in Woodbury, Connecticut, spans from March to May, when the town comes alive with vibrant spring blooms and outdoor activities. This period is particularly popular for those seeking a refreshing getaway, as the milder temperatures (around 10 to 20 degrees Celsius) create great conditions for exploring local parks and enjoying scenic walks.July also attracts a good number of visitors, making it a lively time to experience local events and festivals. The warm summer weather is ideal for outdoor adventures, whether you're hiking in nearby nature reserves or visiting charming shops and eateries in the area. However, be prepared for a bustling atmosphere, as many fellow travellers flock to Woodbury during this month.If you're looking for a more budget-friendly option, visiting in December offers a unique charm as the town is beautifully decorated for the holiday season. While this is considered the low season, it provides a wonderful opportunity to enjoy festive events and a quieter atmosphere, great for those who appreciate a more relaxed holiday experience.Ultimately, the best time to visit Woodbury depends on your preferences.
What are the top attractions in Woodbury?
In Woodbury, Connecticut, visitors can enjoy a blend of natural beauty and historical charm. The town is renowned for its scenic landscapes and outdoor activities, particularly at the picturesque Lake Quassapaug, which offers opportunities for swimming, fishing, and picnicking. The nearby Flanders Nature Centre provides trails for hiking and birdwatching, making it a great spot for nature enthusiasts.For those interested in history, the Woodbury Public Library and the Old Town Hall are popular landmarks that reflect the town's rich heritage. The local antique shops and boutiques along Main Street offer a unique shopping experience, showcasing the area's artisanal crafts and vintage finds.
Are all fees included in the Woodbury 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 Woodbury holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woodbury 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 Woodbury holiday homes?
You can find great discounts on holiday homes in Woodbury 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 Woodbury holiday home booking on Stayz?
To find Woodbury 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 Woodbury?
A long-stay holiday home in Woodbury 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 Woodbury holiday home?
Book your Woodbury 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 Woodbury?
Prices for holiday homes in Woodbury 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 Woodbury 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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