Lakeville holiday lettings

We found 153 holiday rentals — enter your dates for availability

Discover a selection of 14 homes and other holiday rentals in Lakeville that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Lakeville

Showing deals for:12 Dec - 19 Dec

Image gallery for A Country Lodge Straight Out of the Pages of a Great Novel

Exterior
10 out of 10 rating
Exceptional
(13 reviews)

A Country Lodge Straight Out of the Pages of a Great Novel

Pine Plains, NY

8% off
Price is £5,594
for 7 nights, 1 home
£799 per night
includes taxes & fees
A Country Lodge Straight Out of the Pages of a Great Novel

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Find out more about Lakeville

Find out more about Lakeville

Why visit Lakeville

  • Outdoor Adventures: Lakeville is a haven for outdoor enthusiasts, with access to national and state parks, perfect for hiking, biking, and exploration.
  • Scenic Beauty: Enjoy the tranquil landscapes of Long Pond and Hopewell Park, ideal for relaxation and romantic strolls.
  • Charming City Centre: Discover quaint shops and local eateries in Lakeville's delightful city centre.
  • Rich History: Explore nearby Plymouth County, known for its friendly atmosphere and historical significance.
  • Varied Accommodation: Choose from charming cottages, private homes, or convenient apartments for a memorable stay.

Popular types of accommodation in Lakeville

Lakeville boasts an array of delightful vacation rentals, including private homes, charming cottages, and convenient apartments. Whether you're seeking a spacious house rental for a family getaway or a cosy lakeside cottage for a romantic retreat, you'll find the perfect spot. Explore our comprehensive listings for Lakeville rentals and uncover the ideal accommodation to suit your needs. Your memorable escape awaits in this picturesque destination!

  • Houses: The top choice for visitors in Lakeville, ideal for families or groups seeking comfort and privacy.
  • Cottages: A charming option for those wanting a quaint and cosy atmosphere, perfect for a relaxing getaway.
  • Apartments: A convenient choice for solo travellers or couples, offering the essentials for a comfortable stay.
  • Cabins: A rustic retreat that allows guests to immerse themselves in nature while enjoying modern amenities.
  • Chalets: A delightful accommodation type that combines luxury and a picturesque setting, great for a memorable holiday.**

Top attractions in and around Lakeville

Lakeville, Connecticut, is ideal for outdoor enthusiasts seeking scenic and romantic getaways. Its attractions include national and state parks, nature reserves, and museums, making it perfect for those desiring eco-friendly experiences and adventure. Whether travelling solo, as a couple, or with family, you'll find plenty to explore in this charming locale.

  • Harney and Sons Tea Tasting Room: Experience an exquisite selection of fine teas in a charming setting. Enjoy guided tastings and learn about the art of tea blending, surrounded by the delightful aroma of fresh brews.
  • Mount Frissell: Embark on an outdoor adventure at Connecticut's highest peak. Revel in breathtaking scenery, with stunning vistas and serene hiking trails that showcase the region's natural beauty.
  • Holley-Williams House Museum: Discover local history and culture at this preserved museum, featuring fascinating exhibits on the area's heritage and the lives of its past residents.

Things to do recommended for couples

Planning a romantic getaway in Lakeville? Enjoy an enchanting evening at Music Mountain, just 4.3km away, or indulge in wine tasting at Millbrook Vineyards and Winery, 9.3km from your stay. Don't miss the charm of Land of Nod Vineyard and Winery, located 5.0km away.

Things to do recommended for families

During your family vacation in Lakeville, Connecticut, enjoy a day at Veterans Field, only 3.7km away, or relax at Stissing Lake Park, 7.5km distant. For more outdoor fun, visit Stanford Recreation Park, located 9.3km from Lakeville, all offering lovely wellness vibes.

Things to do recommended for groups

Experience the thrill of motor racing at Lime Rock Park, enjoy scenic hikes along the Harlem Valley Rail Trail, or immerse yourselves in culture and entertainment at the TriArts Sharon Playhouse, all within a short drive from Lakeville, Connecticut.

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

If you’re planning a trip with a group, family, or pets, or if you’re considering an extended stay, be sure to apply the appropriate filters to suit your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Lakeville with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can refine your search for all these options and more on Vrbo.
  • Traveling to Lakeville with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lakeville: For many, a family holiday wouldn't feel complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lakeville: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the ideal spot. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly accommodations. Don't forget to include options such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Lakeville

Lakeville, Connecticut, offers a delightful mix of outdoor adventures and serene scenery, making it perfect for a romantic getaway or a relaxing holiday. Explore the charming city centre, unwind at Hopewell Park, or enjoy the tranquil beauty of Long Pond. Nearby, the friendly atmosphere and rich history of Plymouth County await, providing a unique blend of relaxation and adventure for every traveller.

  • Salisbury: Salisbury is a picturesque town located merely 1.2km from Lakeville, renowned for its stunning outdoor landscapes and romantic ambiance. Visitors flock to this charming locale for activities such as motor racing and skiing, with the nearby ski fields offering thrilling winter sports. The area is home to several notable landmarks, including serene lakes and a vibrant stadium, as well as access to the beautiful national state park, making it an ideal spot for nature enthusiasts and adventurers alike. Enjoy a leisurely stroll through the scenic surroundings or indulge in a picnic by the lake, soaking up the tranquil atmosphere.
  • Lime Rock: Lime Rock, a quaint village situated within Lakeville, is a haven for sports and adventure lovers. With its close proximity to motor racing events and a variety of outdoor recreational areas, this village promises an exhilarating experience for those seeking thrills. The local attractions include a stadium, picturesque lakes, and access to the nearby national state park, offering ample opportunities for exploration and adventure. Whether you're racing around the track or enjoying the natural beauty, Lime Rock is an exciting destination for anyone keen on outdoor pursuits.
  • Millerton: Located 2.5km from Lakeville, Millerton is an inviting city that captures the essence of outdoor adventure and scenic beauty. This vibrant destination is perfect for those who enjoy skiing, with ski fields and motor racing activities readily accessible. Visitors can explore the stunning landscapes, including tranquil lakes and majestic mountains, all while being close to the national state park. Millerton offers a delightful balance of adventure and relaxation, making it a wonderful stop for those looking to immerse themselves in nature’s splendour.

Best time to go to Lakeville

If you're planning a trip to Lakeville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudyAverageSlightly Low
February26.4°F (-3.1°C)Light RainMostly CloudyModerately LowAverage
March34.2°F (1.2°C)Light RainMostly CloudyAverageSlightly Low
April45.9°F (7.7°C)Light RainMostly CloudyAverageSlightly Low
May57.2°F (14.0°C)Light RainMostly SunnyAverageAverage
June65.1°F (18.4°C)Light RainMostly SunnyModerately HighAverage
July71.4°F (21.9°C)Light RainMostly SunnyModerately HighAverage
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighSlightly High
September62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
October51.3°F (10.7°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly SunnyModerately LowSlightly High
December30.9°F (-0.6°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a convenient platform to plan new trips, pick up where you last stopped, or effortlessly view and organise your travel arrangements. You can easily access the properties you’ve previously saved and booked, now neatly categorised under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Friendly Lakeville will entice you

Enjoy the museums and other features of Lakeville. Travellers appreciate the restaurants in this welcoming city. 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.

Sightseeing in and around Lakeville

Do you want to find things to do while you're in the area? Venture out of your holiday home and check out everything that makes Lakeville a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mohawk Mountain Ski Area (11.1 mi / 17.9 km)
  • Catamount Ski Area (14.1 mi / 22.7 km)
  • Millbrook Vineyards and Winery (15.3 mi / 24.6 km)
  • Lake Taghkanic State Park (16.2 mi / 26 km)
  • Ski Butternut (16.3 mi / 26.2 km)
  • Hopkins Vineyard (18.5 mi / 29.7 km)

Exploring the natural landscape of Lakeville

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Lakeville. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Mount Frissell (1.5 mi / 2.4 km)
  • Great Falls (3.5 mi / 5.6 km)
  • Harlem Valley Rail Trail (3.8 mi / 6.1 km)
  • Mohawk Mountain State Forest (11.7 mi / 18.8 km)
  • Kent Falls State Park (13 mi / 21 km)
  • Copake Lake (14.7 mi / 23.7 km)

Travelling to and around Lakeville

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 26.7 mi (43 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 32.7 mi (52.7 km) away.

Frequently asked questions

What is the best area to stay in Lakeville when booking a holiday rental?
When considering a holiday rental in Lakeville, Connecticut, the Lakeville village itself is an excellent choice. This quaint area offers a charming small-town atmosphere, making it superb for those looking to unwind while still being close to local attractions. One of the standout features of Lakeville is its proximity to the picturesque Lake Wononscopomuc, which is popular for swimming, kayaking, and fishing, providing a serene backdrop for relaxation.

Another appealing aspect of staying in Lakeville is the easy access to the scenic trails of the nearby Salisbury Nature Preserve. This area not only showcases the natural beauty of the region but also offers fantastic opportunities for hiking and exploring the lovely landscapes. There are numerous holiday rental properties available in Lakeville, allowing visitors to choose from a range of options that suit their preferences, whether they prefer a charming cottage or a more modern home.
How much does it cost to rent a holiday home in Lakeville?
Prices for holiday rentals in Lakeville 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 Lakeville 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 Lakeville holiday house rentals?
You can find great discounts on house rentals in Lakeville 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 Lakeville ski resort rentals?
For skiing in Lakeville, Connecticut, the nearby Mohawk Mountain Ski Area is the main destination for winter sports enthusiasts. Travellers seeking ski resort rentals should consider the charming town of Lakeville itself, where a variety of accommodations are available, including cozy cabins and modern condos. Many of these properties feature amenities such as fully equipped kitchens, comfortable living areas, and in some cases, fireplaces that add to the warm atmosphere after a day on the slopes.

The area around Lakeville offers easy access to Mohawk Mountain, which is just a short drive away. Here, visitors can enjoy a range of winter activities, and the proximity of local shops and restaurants enhances the convenience for those staying in the area. Additionally, many rentals provide outdoor spaces, great for unwinding and taking in the beautiful winter landscapes.
What is the most popular type of holiday rental accomodation in Lakeville?
In Lakeville, holiday houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties typically offer spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many cottages feature charming designs and outdoor spaces, allowing guests to enjoy the serene surroundings and beautiful views of the nearby lakes.
Are there any family house rentals in Lakeville?
In Lakeville, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for groups seeking a retreat. The area is known for its picturesque landscapes and proximity to outdoor activities. Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces for children to enjoy.
Can I rent a holiday home with a pool or hot tub in Lakeville?
In Lakeville, there are several holiday homes available for rent that feature pools or hot tubs. This picturesque town, located in the scenic Litchfield Hills, offers a tranquil escape with its beautiful landscapes and nearby Lake Wononscopomuc. Many properties come equipped with private pools, hot tubs, and outdoor spaces ideal for relaxation and family gatherings. Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and access to beautiful gardens or patios.
Can I find long-stay holiday rentals in Lakeville?
A long-stay holiday rental in Lakeville 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 Lakeville?
In Lakeville, Connecticut, there are several pet-friendly house rentals available, making it a great destination for those travelling with furry companions. Visitors can expect amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ideal for relaxing after a day of exploration. Many of these properties also feature outdoor spaces like patios or decks, superb for enjoying the serene surroundings.
Are there any remote work holiday rentals in Lakeville?
In Lakeville, Connecticut, there are several remote work holiday rentals available that cater to those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including dedicated office spaces, desks, chairs, and high-speed Wi-Fi, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lakeville holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lakeville 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 Lakeville?
In Lakeville, popular holiday rental amenities include well-equipped kitchens, which are essential for guests who enjoy cooking during their stay. Most rentals provide a dishwasher, cookware, dishware, and utensils, making meal preparation convenient and enjoyable. Additionally, many properties feature an oven, allowing for a range of cooking options.
When is the best time to visit Lakeville for a holiday rental?
The best time to visit Lakeville for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This summer period is ideal for those who enjoy outdoor activities such as hiking, kayaking, and exploring the beautiful lakes that define this charming Connecticut town. The warm temperatures, typically ranging from the mid-20s to low 30s Celsius, create a great backdrop for enjoying the natural beauty and vibrant community events that Lakeville has to offer.

During this time, visitors can partake in various local festivals and farmers' markets, all while soaking up the sun and engaging with fellow travellers who share a passion for adventure and relaxation. The atmosphere is lively, and you'll find plenty of opportunities for socialising and exploring the scenic surroundings.

For those looking for a more budget-friendly option, consider visiting Lakeville in December. While this is the low season, it offers a unique charm with winter landscapes and a peaceful ambience. The town transforms into a winter wonderland, great for cosy retreats and enjoying the festive spirit without the crowds.
How early should I book a Lakeville holiday rental?
Book your Lakeville 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 Lakeville home rental booking on Vrbo?
To find Lakeville 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 Lakeville 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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