Lakeville vacation rentals

We found 156 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Lakeville that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You're sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Lakeville

Showing deals for:Dec 19 - Dec 26

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10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

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

Pine Plains, NY

9% off
Price is $948
$6,636 for 7 nights
All fees included
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 offers stunning scenery for hiking, fishing, and exploring national parks and nature reserves.
  • Charming Neighborhoods: Enjoy the welcoming atmosphere and picturesque streets perfect for leisurely strolls.
  • Romantic Getaways: Ideal for couples seeking a peaceful retreat amidst beautiful surroundings.
  • Historic Day Trips: Conveniently located for exploring nearby historic sites and attractions, including New York.
  • Diverse Accommodations: Choose from cozy cottages, spacious homes, or stylish apartments to suit your needs.

Popular types of accommodation in Lakeville

Lakeville offers a diverse selection of vacation rentals to suit every traveler's needs. Whether you're looking for spacious houses, charming cottages, or convenient apartments, you'll find the perfect fit here. Our platform makes searching for vacation rentals easy, whether you need a cozy bedroom cottage or a stylish apartment in Lakeville. Discover your ideal getaway and enjoy transparency, savings, and peace of mind during your stay.

  • Houses: The top choice for visitors, these homes offer spacious and comfortable settings, perfect for families or groups looking to enjoy Lakeville together.
  • Cottages: These charming and cozy retreats provide a quaint atmosphere for those seeking a peaceful getaway amidst nature.
  • Apartments: Ideal for couples or solo travelers, apartments offer convenience and easy access to local attractions.
  • Cabins: Rustic and inviting, cabins are a popular option for those wanting to immerse themselves in the great outdoors.
  • Chalets: These stylish mountain lodges combine comfort with stunning views, making them a favored option for a unique stay.**

Top attractions in and around Lakeville

Lakeville, Connecticut, is a perfect destination for outdoor enthusiasts and those seeking romantic getaways. With its stunning scenery, visitors can explore a variety of attractions, including national parks, nature reserves, and museums. Whether you’re looking for adventure or a peaceful retreat, Lakeville offers a range of activities that cater to all types of travelers, making it an ideal spot for unforgettable experiences in nature.

  • Harney and Sons Tea Tasting Room: Located just a mile from Lakeville, this charming tea room offers a delightful experience for tea enthusiasts. Sample an array of high-quality teas while enjoying the cozy atmosphere and knowledgeable staff who can guide you through the flavors of their finest blends.
  • Mount Frissell: Also a mile away, Mount Frissell is the highest peak in Connecticut, providing breathtaking views and a chance for outdoor exploration. Hike the scenic trails and immerse yourself in the natural beauty of the surrounding landscape.
  • Holley-Williams House Museum: Situated within Lakeville, this historic museum showcases local culture and heritage. Visitors can explore its well-preserved rooms and learn about the area's rich history through engaging exhibits and guided tours.

Things to do recommended for couples

If you're seeking a romantic getaway in Lakeville, Connecticut, consider catching a concert at Music Mountain, just 7 miles away. You can also enjoy wine tasting at the charming Land of Nod Vineyard and Winery, 8 miles from town, or visit Millbrook Vineyards and Winery, 15 miles away, for a delightful experience.

Things to do recommended for families

Your family will love exploring the wellness vibes at Veterans Field, just 6 miles away, Stissing Lake Park, 12 miles away, and Stanford Recreation Park, 15 miles away. Each offers a perfect setting for relaxation and fun outdoor activities for all ages.

Things to do recommended for groups

Groups visiting Lakeville can enjoy thrilling races at Lime Rock Park, hike the scenic Harlem Valley Rail Trail just 4 miles away, and experience culture and entertainment at the TriArts Sharon Playhouse, located 6 miles from Lakeville. Each offers unique adventures for everyone.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, your family, pets, or planning extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Lakeville with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Lakeville with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lakeville: For many families, a vacation wouldn’t feel whole without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly properties 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 vacation rentals offering special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Lakeville

Lakeville, Connecticut, offers a delightful blend of outdoor adventures and charming scenery, perfect for a romantic getaway or a refreshing vacation. Explore its welcoming neighborhoods, breathe in the fresh air, and indulge in the friendly atmosphere. Nearby, you can discover the historic vibes of the region, making it an ideal base for day trips to New York or other picturesque locales. Enjoy the best of Lakeville and its surrounding areas for a truly memorable experience.

  • Salisbury: Located 2 miles from Lakeville, Salisbury is a charming city known for its stunning outdoor scenery and romantic ambiance. It attracts travelers seeking adventure and relaxation alike. Outdoor enthusiasts can enjoy activities like motor racing and skiing, particularly at the nearby ski fields. The area is also home to beautiful lakes, a stadium, and the picturesque national state park, making it a perfect spot for nature lovers and those looking to unwind in a scenic setting.
  • Millerton: Situated 4 miles from Lakeville, Millerton is a vibrant city that offers a blend of outdoor adventure and breathtaking scenery. Visitors flock to this area for skiing and motor racing, with easy access to ski fields and a variety of recreational activities. The surrounding natural beauty includes serene lakes, the majestic national state park, and nearby mountains, creating an ideal backdrop for hiking, exploring, and enjoying the great outdoors.
  • Lime Rock: Nestled within the Lakeville area, Lime Rock is a quaint village that draws visitors for its sports and outdoor adventures. Known primarily for its motor racing events, Lime Rock also offers a recreational area and skiing opportunities. Local attractions include a stadium, beautiful lakes, and the expansive national state park, providing ample opportunities for sports enthusiasts and nature lovers to engage in activities that highlight the region's striking landscape.

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 simple

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

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. By enrolling in our One Key travel rewards program, you can quickly access member discounts and earn as well as use OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Friendly Lakeville will entice you

Enjoy the museums and other features of Lakeville. Travelers appreciate the restaurants in this welcoming city. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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

Are you looking for top things to see and do while you're in the area? Venture out of your cozy vacation rental and check out everything that Lakeville has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 looking for exciting outdoor activities or just want to spend some time taking in the scenery, Lakeville is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Lakeville

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 26.7 mi (43 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying 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 vacation rental?
When planning a vacation rental in Lakeville, Connecticut, the charming area surrounding Lakeville Lake is an excellent choice. This picturesque neighborhood offers a serene atmosphere with stunning views and opportunities for outdoor activities. Staying near the lake provides easy access to swimming, kayaking, and fishing, which are popular pastimes among both locals and visitors.

Additionally, you'll find the nearby Salisbury Central School, which adds to the community feel of the area. The region is also a short drive from the Appalachian Trail, making it a fantastic base for hiking enthusiasts who want to explore the beautiful Connecticut wilderness.

Another appealing area is the Historic District of Lakeville, where you can immerse yourself in the town's rich heritage. This part of Lakeville features beautifully preserved architecture and is close to attractions like the Lakeville Historical Society, which offers insight into the local history and culture.
How much does it cost to rent a vacation home in Lakeville?
Prices for vacation 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 vacation 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 areas for renting a beach house in Lakeville?
For renting a beach house in Lakeville, Connecticut, travelers should look towards the nearby Lakeville Lake and the surrounding Litchfield County area. The lakeside properties around Lakeville Lake provide a serene setting, with many rentals featuring amenities such as private docks, outdoor decks, and spacious lawns superb for family gatherings or relaxation by the water. These homes often come equipped with full kitchens, allowing guests to prepare meals and enjoy dining al fresco while taking in the picturesque views.

Additionally, the nearby town of Salisbury offers charming vacation rentals with easy access to the lake and scenic hiking trails in the surrounding Appalachian Mountains. Many of these accommodations possess cozy interiors with fireplaces, outdoor seating areas, and sometimes even access to communal amenities, such as swimming areas or picnic spots. The region is known for its natural beauty, with opportunities for boating, fishing, and kayaking on the lake, as well as exploring the local shops and restaurants in the quaint downtown area.

For those seeking a more rustic experience, there are also cabins and cottages available in the nearby hills, offering a retreat-like feel with amenities like fire pits, BBQ grills, and wood-burning stoves.
Where are the best Lakeville ski resort rentals?
For ski resort rentals near Lakeville, Connecticut, travelers should consider the nearby Mohawk Mountain Ski Area located in Cornwall, which is just a short drive away. In the Cornwall area, visitors can find cozy cabins and chalets that provide a rustic escape with modern comforts. Many of these properties come with amenities such as fireplaces, outdoor decks, and fully equipped kitchens, great for relaxing after a day on the slopes.

Additionally, the town of Lakeville itself offers charming accommodations, including historic inns and lakeside cottages that provide a tranquil setting. While not directly on the ski slopes, these rentals often feature beautiful views of the surrounding landscape, proximity to local eateries, and access to outdoor activities such as snowshoeing and cross-country skiing in the winter months.

For those willing to venture a bit further, the town of Salisbury offers additional options, where you can find more upscale lodgings that may include features like hot tubs, game rooms, and spacious living areas, making them ideal for families or groups.
What is the most popular type of vacation rental accomodation in Lakeville?
In Lakeville, vacation houses and cottages are the most popular types of rentals, with several options available throughout the area. These accommodations often feature charming designs that blend with the picturesque surroundings. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios to enjoy the scenic views of the nearby lakes and countryside. Many properties also include cozy fireplaces and modern appliances, enhancing the comfort of a home-like stay.
Are there any family house rentals in Lakeville?
In Lakeville, Connecticut, there are several family-friendly house rentals available, making it a great choice for families looking to explore the area. The homes typically feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces where children can play safely. Many properties also offer amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for guests.

This picturesque town is located near the beautiful Lake Wononscopomuc, which is great for swimming, kayaking, and picnicking. Nearby, visitors can explore the scenic landscapes of the Litchfield Hills, ideal for hiking and enjoying nature.
Can I rent a vacation home with a pool or hot tub in Lakeville?
In Lakeville, Connecticut, several vacation homes are available for rent that feature pools or hot tubs, making it an excellent choice for travelers seeking relaxation and leisure. The area is known for its picturesque landscapes and serene atmosphere, particularly around Lake Wononscopomuc, where you can find properties that offer beautiful views and easy access to outdoor activities.

Many of these rentals come equipped with private pools and hot tubs, along with spacious outdoor areas superb for family gatherings or quiet evenings under the stars. Inside, you can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even game rooms or home theaters, enhancing your vacation experience.
Can I find long-stay vacation rentals in Lakeville?
A long-stay vacation rental in Lakeville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Lakeville?
In Lakeville, Connecticut, travelers will find several pet-friendly house rentals that cater to both comfort and convenience. Many of these vacation homes are equipped with amenities such as fully stocked kitchens, spacious yards, and cozy living areas, making them great for families or groups traveling with pets. The area is known for its serene environment, with properties often featuring outdoor spaces where pets can enjoy the fresh air.

The Lakeville area boasts proximity to various parks and natural attractions, providing ample opportunities for outdoor activities. Nearby, the Lakeville Lake offers scenic views and tranquil settings for leisurely walks with pets. Additionally, the charming town center features pet-friendly cafes and shops, allowing for enjoyable outings without leaving your furry friends behind.
Are there any remote work vacation rentals in Lakeville?
In Lakeville, Connecticut, there are several vacation rentals suitable for remote work. Travelers can expect properties that are well-equipped with amenities designed to facilitate a productive work environment. Many rentals feature dedicated office spaces, high-speed Wi-Fi, and comfortable desks with chairs, ensuring you can work efficiently while enjoying a tranquil getaway.

The scenic beauty of Lakeville, with its proximity to Lake Wononscopomuc and the surrounding Litchfield Hills, offers a superb balance of work and leisure. After hours, you can explore local attractions like the scenic hiking trails in the nearby Taconic State Park or relax by the lake. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lakeville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lakeville with parking available—perfect for families or travelers 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 vacation rental amenities include kitchens equipped with essential appliances such as blenders and coffee/tea makers, allowing guests to prepare their own meals. Many rentals feature kitchen islands that provide additional cooking space and a social hub for gatherings. WiFi is also commonly available, ensuring travelers can stay connected during their stay.
When is the best time to visit Lakeville for a vacation rental?
July is the most popular time to visit Lakeville, Connecticut, as it coincides with the peak season from June to August. During these months, the area comes alive with vibrant outdoor activities and a lively atmosphere. Travelers can indulge in various summer pursuits, such as hiking, boating on Lake Wononscopomuc, and exploring the picturesque hiking trails that surround the region.

With average temperatures ranging from the mid-60s to the low 80s Fahrenheit, July offers the superb climate for outdoor adventures and leisurely strolls by the lake. This warm weather creates a comfortable setting for sightseeing and enjoying the natural beauty that Lakeville has to offer.

If you're looking for a more budget-friendly option, consider planning your visit in December. While the temperatures drop to the low 20s to mid-30s Fahrenheit, you can enjoy a cozy winter atmosphere and fewer crowds, allowing for a peaceful getaway.
How early should I book a Lakeville vacation rental?
Book your Lakeville vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Lakeville?
In Lakeville, Connecticut, visitors can enjoy a variety of attractions that highlight the town's natural beauty and cultural offerings. The picturesque Lake Wononscopomuc is a central feature, superb for boating, swimming, and fishing, with vacation rentals nearby offering easy access to the water.

The nearby Salisbury Central School hosts community events and is surrounded by charming local shops and cafes that provide a taste of small-town life. For those interested in outdoor activities, the Appalachian Trail runs through the area, offering hiking opportunities with stunning views of the surrounding landscapes.

Additionally, the Salisbury Winter Sports Association hosts events that attract visitors during the winter months, while the nearby Housatonic River provides opportunities for kayaking and scenic walks.
Can I change or cancel my Lakeville home rental booking on Vrbo?
To find Lakeville vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 vacation 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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