Lakeville vacation rentals

We found 167 vacation rentals — enter your dates for availability

Discover a selection of 13 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

  • Scenic Getaway: Lakeville offers breathtaking views of the Litchfield Hills, perfect for a romantic escape.
  • Outdoor Adventures: Explore nearby state parks and nature reserves for hiking, fishing, and wildlife watching.
  • Cultural Experiences: Immerse yourself in the rich history and culture of the area through local museums and events.
  • Charming Accommodations: Choose from cozy cottages, modern apartments, or private vacation homes for a perfect stay.
  • Tranquil Lake Visits: Unwind by the serene private Lakeville, surrounded by stunning natural beauty.

Popular types of accommodation in Lakeville

Your adventure in Lakeville awaits, and selecting the perfect vacation rental is the first step. Explore our wide array of options, including charming houses, cozy cottages, and modern apartments. Whether you prefer a relaxing evening in a spacious living room or grilling outdoors, Lakeville has the ideal setting for your getaway. Discover the ideal cottage in Lakeville today and make your stay unforgettable.

  • Houses: The top choice for travelers in Lakeville, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Cottages: A close second, these quaint and cozy retreats provide a charming atmosphere ideal for a peaceful getaway.
  • Apartments: Convenient and versatile, apartments are a popular option for visitors looking for a home-like stay in the heart of Lakeville.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic escape surrounded by beautiful landscapes.
  • Chalets: These inviting structures combine comfort and style, making them a lovely choice for those seeking a unique experience.**

Top attractions near Lakeville

Lakeville, Connecticut, is perfect for a romantic and scenic getaway, offering a blend of outdoor adventures and eco-friendly experiences. Explore the nearby national state parks, nature reserves, and museums, which cater to nature lovers and adventure seekers alike. Additionally, for a more tranquil experience, consider visiting the private Lakeville, where you can unwind and enjoy the beautiful surroundings.

  • Bash Bish Falls State Park: Experience the breathtaking beauty of cascading waterfalls surrounded by lush greenery. This park offers scenic hiking trails and opportunities for adventure amidst nature's splendor.
  • Harney and Sons Tea Tasting Room: Delight in a charming tea experience just a mile away. Sample a variety of exquisite teas while enjoying the cozy ambiance, perfect for tea enthusiasts and adventurers alike.
  • Mount Frissell: Stand atop the highest point in Massachusetts, where stunning panoramic views await. Enjoy hiking trails and the serene outdoor vibes that this picturesque peak has to offer.

Things to do recommended for couples

Lakeville offers charming experiences for couples, like a scenic hike at the nearby Appalachian Trail, ending with a picnic by the serene Lake Wononscopomuc. For a cozy evening, enjoy a candlelit dinner at a local bistro, savoring exquisite flavors while surrounded by beautiful views.

Things to do recommended for families

Families can explore the scenic Lake Wononscopomuc for swimming and kayaking, enjoy hiking at the nearby Appalachian Trail, or visit the local shops and eateries in downtown Lakeville for a taste of small-town charm.

Things to do recommended for groups

Groups visiting Lakeville can enjoy outdoor activities like hiking the scenic trails of the Appalachian Trail or kayaking on Lake Wononscopomuc. Don't miss a visit to the local farms for fresh produce and a taste of authentic Connecticut cuisine.

*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

When planning your trip—whether you're traveling with a group, spending time with family, bringing along pets, or seeking longer accommodations—be sure to use the appropriate filters to meet your priorities. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Lakeville with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Lakeville with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to 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 vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and pet beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lakeville: If you're searching for vacation rentals with special offers for extended stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Additionally, think about including features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Lakeville

Lakeville, Connecticut, offers a charming blend of outdoor adventures and romantic scenery, making it a perfect getaway. Nestled in the picturesque Litchfield Hills, visitors can explore rolling hills, serene lakes, and a close-knit community with friendly locals. Immerse yourself in the area's rich culture and history while enjoying the breathtaking beauty that surrounds this small town. Whether you seek relaxation or adventure, Lakeville promises an unforgettable travel experience.

  • Salisbury: Located a mere 2 miles from Lakeville, Salisbury is a picturesque city known for its stunning outdoor scenery and romantic ambiance. Travelers flock to Salisbury for its breathtaking landscapes, where outdoor enthusiasts can indulge in activities like motor racing and skiing. Highlights include nearby lakes and the Salisbury National State Park, perfect for hiking and enjoying nature. Visitors can also catch exciting events at the local stadium, making it an ideal spot for both relaxation and adventure.
  • Lime Rock: Nestled in the area surrounding Lakeville, Lime Rock is a vibrant village that attracts those seeking sports and outdoor adventures. Its proximity to motor racing venues offers thrilling experiences for racing fans. Lime Rock is also home to charming shopping areas and scenic boardwalks, perfect for leisurely strolls. With local attractions such as lakes and museums, visitors can immerse themselves in the rich culture and natural beauty of the region.
  • Millerton: Just 4 miles from Lakeville, Millerton is a charming city that offers a delightful mix of outdoor activities and scenic beauty. Known for its adventurous spirit, Millerton provides opportunities for skiing and motor racing, catering to thrill-seekers. The surrounding landscape features stunning mountains and lakes, inviting visitors to explore the great outdoors. With the nearby National State Park, Millerton is perfect for those looking to connect with nature while enjoying a variety of recreational activities.

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 vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, or review and organize your reservations. Your saved or booked properties are categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply 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:

  • Harney and Sons Tea Tasting Room (1.3 mi / 2.1 km)
  • 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)

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:

  • 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)
  • Jug End State Reservation (13 mi / 20.9 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, 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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