Lakeville vacation rentals

We found 163 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.

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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)
  • Trevor Zoo (11.8 mi / 19 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)

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:

  • 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)
  • Woodridge Lake (14.8 mi / 23.8 km)
  • Lake Taghkanic State Park (16.2 mi / 26 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, Connecticut, United States of America when booking a vacation rental?
When considering the best area to stay in Lakeville, Connecticut, you'll want to focus on the charming neighborhoods that capture the essence of this picturesque town. One of the standout areas is near the scenic Lakeville Lake, where you can enjoy breathtaking views and a peaceful atmosphere. This area is great for those looking to unwind and appreciate nature, as it offers opportunities for swimming, kayaking, and fishing.

Another appealing neighborhood is close to the town center, where you'll find a delightful mix of boutique shops and local eateries. This location allows you to immerse yourself in the local culture and enjoy easy access to attractions such as the historic Hotchkiss School and the scenic trails of the Appalachian Trail, which are great for hiking enthusiasts.

Overall, Lakeville boasts a variety of vacation rental properties, ranging from cozy cottages to larger homes, suiting different preferences and group sizes.
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, travelers should explore the charming shores of Lake Wononscopomuc, which is the largest natural lake in the area. The eastern side of the lake offers several vacation rentals with direct water access, making it convenient for swimming, kayaking, and fishing. Many properties here come with amenities such as private docks, outdoor decks for sunbathing, and spacious living areas, great for family gatherings or a peaceful retreat.

Additionally, the nearby Lakeville town center provides easy access to local shops and restaurants, enhancing the convenience for visitors. Along the lake, some homes feature outdoor fire pits and picnic areas, ideal for enjoying evenings by the water.

For those interested in outdoor activities, the surrounding Litchfield Hills region offers hiking trails with stunning views and opportunities for exploring the natural beauty of the area. Many rentals in this vicinity provide cozy interiors, fully equipped kitchens, and comfortable furnishings, ensuring a relaxing stay while enjoying the scenic landscape of Lakeville.
Where are the best Lakeville ski resort rentals?
For ski resort rentals near Lakeville, travelers should focus on the nearby area of Salisbury, which is home to the Mohawk Mountain Ski Area, just a short drive away. In Salisbury, visitors can find cozy cabins and charming lodges that offer a rustic atmosphere great for skiers and snow enthusiasts. Many of these properties come equipped with amenities such as wood-burning fireplaces, spacious living areas, and fully equipped kitchens, ideal for gathering after a day on the slopes.

Additionally, the Lakeville area features lakeside cottages and vacation homes that provide a serene backdrop for winter getaways. These rentals often boast stunning views of the surrounding hills and easy access to ice fishing and snowshoeing opportunities on the nearby lakes. Many properties in this region also include outdoor fire pits, hot tubs, and access to local trails, allowing for a blend of relaxation and adventure.
What is the most popular type of vacation rental accomodation in Lakeville?
In Lakeville, vacation houses are the most popular type of rental, with about 11 available in the area. These homes often feature ample space, including multiple bedrooms, fully equipped kitchens, and inviting living areas that make them superb for families or groups. Many also boast outdoor spaces for enjoying the scenic beauty of the surrounding countryside. Additionally, there are several cottages and apartments available, offering a more intimate and cozy atmosphere for travelers looking for a quieter getaway.
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 a family getaway. This picturesque area is known for its stunning lakes and outdoor activities, superb for families looking to explore nature. Many of these homes feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces ideal for children to play or for family gatherings.

Travelers can find properties close to Lakeville Lake, where swimming, kayaking, and picnicking are popular activities. Additionally, nearby attractions such as the Mohawk Mountain Ski Area offer seasonal fun for winter sports enthusiasts, while the scenic views and hiking trails in the surrounding Litchfield Hills provide opportunities for family adventures throughout the year.
Can I rent a vacation home with a pool or hot tub in Lakeville?
In Lakeville, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque town, located in the scenic Litchfield Hills, offers a serene getaway with beautiful natural surroundings. Many properties come equipped with private pools, outdoor hot tubs, and spacious decks, superb for relaxation after a day of exploring the area.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even fire pits for evening gatherings. The tranquil atmosphere of Lakeville is ideal for families or groups looking to unwind, with opportunities for outdoor activities like hiking and boating nearby.
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, there are several pet-friendly house rentals available, making it an excellent destination for travelers looking to bring their furry companions along. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor areas where pets can roam freely. The tranquil setting of Lakeville provides a peaceful retreat with beautiful natural surroundings.

Nearby, the area is known for its outdoor recreational opportunities, including the picturesque Lakeville Lake, which offers activities such as swimming and kayaking. Additionally, the nearby Salisbury and Taconic State Parks provide ample hiking trails, allowing pet owners to enjoy nature while exploring the scenic landscapes.
Are there any remote work vacation rentals in Lakeville?
In Lakeville, Connecticut, there are 11 vacation rentals that cater to remote workers, making it a great choice for those looking to blend work and leisure. Many properties in this area come equipped with essential amenities for a productive stay, such as high-speed Wi-Fi, dedicated office spaces, and desks. Some accommodations even feature printers, ensuring that remote work needs are met comfortably.

Lakeville is known for its picturesque landscapes and serene environment, providing an ideal backdrop for focused work sessions. The charming local community offers access to recreational activities like hiking and boating, allowing for refreshing breaks after a day of work. 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 fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals feature decks or patios, providing outdoor space to relax and enjoy the scenic views of the Connecticut countryside. Fireplaces are common in these properties, adding a cozy touch, especially during the cooler months. Additionally, travelers can expect coffee and tea makers for their morning routines and onsite parking, making it convenient for those driving to the area.
When is the best time to visit Lakeville for a vacation rental?
The peak travel season in Lakeville typically spans from June to August, with July being the most popular month for vacationers. During this time, visitors can revel in the warm summer weather, great for enjoying the natural beauty of the area. With temperatures often reaching the mid-70s to low 80s Fahrenheit, outdoor activities such as hiking, boating on Lake Wononscopomuc, and exploring the scenic trails become particularly inviting.

For those seeking a more tranquil experience, consider visiting Lakeville in December. This quieter month offers a unique charm, with the possibility of winter activities like snowshoeing and cross-country skiing, all set against a picturesque snowy backdrop. Plus, the festive holiday atmosphere adds to the town's appeal during this time.

Ultimately, the best time to book a vacation rental in Lakeville depends on your preference for vibrant summer energy or a serene winter retreat.
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, Connecticut, United States of America?
In Lakeville, Connecticut, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The stunning Lake Wononscopomuc, known for its clear waters and scenic views, is superb for swimming, kayaking, and picnicking along its shores. The town is also home to the historic Hotchkiss School, which offers beautiful grounds and architecture worth exploring.

Outdoor enthusiasts can venture to the nearby Appalachian Trail, where hiking and nature walks provide breathtaking views of the surrounding landscape. The scenic Litchfield Hills region offers opportunities for leaf-peeping in the fall and winter sports in nearby locations.

For a taste of local culture, the Lakeville Art and Historical Society showcases the town's history and artistic endeavors, while charming local shops and eateries provide a quaint experience in the town center.
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 cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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