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New Preston holiday lettings

We found 225 holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in New Preston that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – New Preston

Showing deals for:28 Aug - 4 Sept

Image gallery for Litchfield County Four Season Country Paradise

Front entrance with gate for privacy
9.4 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
Price is £8,003
for 7 nights, 1 home
£1,143 per night
includes taxes & fees
Litchfield County Four Season Country Paradise

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the natural beauty of New Preston

Enjoy the wineries and other features of New Preston. This city is well-known for its parks and beaches. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around New Preston

Are you hoping to find top things to see and do in the area? Venture out of your holiday home and experience everything that makes New Preston a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Hopkins Vineyard (0.9 mi / 1.4 km)
  • The Christmas Shop (8 mi / 12.9 km)
  • Mohawk Mountain Ski Area (9.9 mi / 15.9 km)
  • Quassy Amusement Park (15.3 mi / 24.6 km)
  • Connecticut Valley Winery (17 mi / 27.4 km)
  • Thunder Ridge Ski Resort (17.8 mi / 28.7 km)

Exploring the natural landscape of New Preston

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in New Preston. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lake Waramaug (0.9 mi / 1.5 km)
  • Lake Waramaug State Park (2.3 mi / 3.8 km)
  • Mount Tom State Park (3.3 mi / 5.4 km)
  • Steep Rock Preserve (5.2 mi / 8.3 km)
  • Bantam Lake (6.3 mi / 10.1 km)
  • Kent Falls State Park (6.8 mi / 11 km)

Travelling to and around New Preston

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 18.3 mi (29.5 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 23.5 mi (37.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in New Preston?
Prices for holiday rentals in New Preston 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 New Preston 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 New Preston holiday house rentals?
You can find great discounts on house rentals in New Preston 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.
Where are the best areas for renting a beach house in New Preston?
For renting a beach house in New Preston, Connecticut, the area around Lake Waramaug is an excellent choice. This picturesque lake offers a tranquil setting with several properties situated directly on the water, providing stunning lake views and easy access for swimming and boating. Many of these beach houses come equipped with amenities such as outdoor decks, private docks, and fully furnished kitchens, making them ideal for family gatherings or relaxing getaways.

The nearby town of New Preston itself features quaint shops and local eateries, adding to the charm of the area. Additionally, the scenic landscapes surrounding the lake provide opportunities for hiking and exploring, with some rentals offering proximity to nature trails that wind through the beautiful countryside.
Where are the best New Preston ski resort rentals?
For skiing near New Preston, Connecticut, the closest resort is Mohawk Mountain, located about a 30-minute drive away. In New Preston itself, travellers can find a variety of charming accommodations, including quaint cottages and modern homes that make for a comfortable stay. Many properties in this area come equipped with amenities such as fully stocked kitchens, cozy fireplaces, and spacious living areas, ideal for relaxing after a day on the slopes.

The nearby town of Lakeville also offers additional rental options, often featuring scenic views of the surrounding hills and lakes. Here, visitors can expect amenities like outdoor decks, hot tubs, and easy access to hiking trails during the off-season, enhancing the overall experience.

Furthermore, the New Preston area is known for its picturesque landscapes, with opportunities for winter sports, including cross-country skiing and snowshoeing. Properties often provide proximity to local cafes and shops, allowing travellers to enjoy the quaint charm of the region while being just a short drive from the ski slopes.
What is the most popular type of holiday rental accomodation in New Preston?
In New Preston, holiday houses are the most popular type of holiday rental, with around 33 available in the area. These properties often feature spacious layouts, with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many of these homes also come with outdoor spaces, such as decks or gardens, where guests can relax and enjoy the scenic surroundings. Additionally, there are about 15 cottages available, which provide a charming and quaint alternative for those seeking a more rustic experience. A few cabins can also be found, offering a unique stay in a natural setting.
Are there any family house rentals in New Preston?
In New Preston, Connecticut, there are some family-friendly house rentals available, with around 14 options to choose from. This charming village, located by the picturesque Lake Waramaug, offers a wonderful setting for families seeking a tranquil getaway. Properties in the area often feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can enjoy the fresh air.

Visitors can explore the natural beauty of the lake, which is ideal for swimming, picnicking, and boating. Nearby, the town boasts quaint shops and local eateries, allowing families to experience the charm of New Preston's small-town atmosphere.
Can I rent a holiday home with a pool or hot tub in New Preston?
In New Preston, there are several holiday homes available for rent that feature pools and hot tubs. This charming area, known for its picturesque landscapes and proximity to Lake Waramaug, offers a serene retreat for travellers. Many of these properties provide amenities such as private pools, hot tubs, and spacious outdoor areas for relaxation and entertainment. Additionally, fully equipped kitchens and comfortable living spaces are common, making them ideal for families or groups looking to enjoy a leisurely getaway.
Can I find long-stay holiday rentals in New Preston?
A long-stay holiday rental in New Preston 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 New Preston?
In New Preston, there are several pet-friendly house rentals available, offering a variety of amenities to accommodate travellers and their furry companions. Many of these properties feature comfortable living spaces, fully equipped kitchens, and outdoor areas such as gardens or patios where pets can enjoy the fresh air.

The charming community is located near Lake Waramaug, which not only provides picturesque views but also opportunities for outdoor activities. The lake area is ideal for leisurely walks, and there are nearby hiking trails that cater to pet owners looking to explore the beautiful surroundings.

Additionally, the local shops and cafes often welcome pets, creating a friendly feel for visitors with animals.
Are there any remote work holiday rentals in New Preston?
In New Preston, Connecticut, there are a variety of remote work holiday rentals available, with approximately 51 options to choose from. This charming town, located in the Litchfield Hills, offers an ideal setting for those looking to combine work and leisure. Many of the properties feature essential amenities for remote work, such as high-speed Wi-Fi, dedicated workspaces, and printers, ensuring a productive environment.

The picturesque surroundings provide an excellent backdrop for breaks, with opportunities for outdoor activities like hiking and exploring nearby lakes. The town itself is close to local shops and cafes, offering a delightful mix of convenience and charm for extended stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any New Preston holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in New Preston 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 New Preston?
In New Preston, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals comfortably. Many properties feature decks or patios, providing lovely outdoor spaces for relaxation or alfresco dining while soaking in the picturesque surroundings. A fireplace is often included, adding a cosy touch for those cooler evenings. Additionally, rentals typically come with coffee and tea makers, ensuring that guests can enjoy their favourite hot beverages anytime. Onsite parking is also a common amenity, making it convenient for travellers with vehicles.
When is the best time to visit New Preston for a holiday rental?
The best time to visit New Preston for a holiday rental is during the peak season from May to July. This vibrant period attracts visitors eager to enjoy the charming scenery and outdoor activities that the area has to offer. July, in particular, is the most popular month, when the warm weather invites travellers to explore the picturesque Lake Waramaug and the surrounding state parks, great for hiking and picnicking under the sun.

During these months, you can expect comfortable temperatures ranging from 15 to 30 degrees Celsius, ideal for outdoor sightseeing and leisurely strolls through the quaint town. The lively option during this time is complemented by local events, farmers' markets, and opportunities for water-based activities, providing a fulfilling experience for all.

For those looking for a more budget-friendly option, consider visiting in November. This month presents a quieter and more peaceful side of New Preston, allowing visitors to enjoy the stunning autumn colours and the tranquil beauty of the area without the crowds. Although the temperatures drop to about 0 to 10 degrees Celsius, the serene atmosphere makes it great for cosy indoor activities or enjoying a hot beverage at a local café.

Ultimately, your choice will depend on whether you prefer the energetic buzz of peak season or the quiet charm of the off-peak months.
How early should I book a New Preston holiday rental?
Book your New Preston 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.
What are the top attractions in New Preston?
In New Preston, Connecticut, visitors can enjoy a charming and picturesque experience amidst the scenic beauty of the Litchfield Hills. One of the top attractions is Lake Waramaug, where guests can partake in various water activities or simply relax by the shore, enjoying the tranquil surroundings. The area is renowned for its stunning fall foliage, making it a superb spot for nature lovers and photographers alike.

The historic village centre features quaint shops, art galleries, and local eateries that embody the New England charm. Nearby, the scenic Washington Depot offers access to the famous Steep Rock Preserve, where hiking trails and beautiful views of the Housatonic River can be explored.
Can I change or cancel my New Preston home rental booking on Vrbo?
To find New Preston 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 cabin or a beach house, 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 New Preston 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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