Lakeville holiday lettings

We found 164 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:23 Oct - 30 Oct

Image gallery for TREEMENDOUS VIEWS COTTAGE

kitchen island w/reclaimed wood
10 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

7% off
Price is £3,054
for 7 nights, 1 room
£436 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE

Find spaces that suit your style

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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)
  • 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 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:

  • Harlem Valley Rail Trail (3.8 mi / 6.1 km)
  • Thompson Pond (11.6 mi / 18.7 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)

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 area surrounding the picturesque Lakeville Lake itself is highly recommended. This charming neighbourhood offers a serene atmosphere and stunning views, making it an ideal spot for relaxation and outdoor activities. Here, you can enjoy various properties that range from quaint cottages to spacious family homes, all designed to enhance your stay.

A top attraction in the vicinity is the Lakeville Lake, which is superb for swimming, kayaking, and fishing, providing a lovely backdrop for your holiday. Additionally, the nearby Salisbury Central School offers community events and seasonal activities, which can be an enjoyable way to engage with local culture.

Another appealing area to consider is the historic centre of Lakeville, where you can find an array of delightful shops, cafes, and restaurants. The scenic landscapes and rich history of the region create an inclusive setting for visitors.
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 areas for renting a beach house in Lakeville?
For renting a beach house in Lakeville, Connecticut, the area around Lake Wononscopomuc is ideal. This picturesque lake offers a serene setting for holiday rentals, with many properties providing stunning water views and direct access to the beach. Travellers can expect amenities such as private docks, outdoor seating areas, and barbecues, great for enjoying warm summer evenings by the water.

Additionally, properties in the nearby town of Salisbury also offer attractive options, often featuring spacious gardens and fire pits for relaxing after a day of swimming or boating. The charming local shops and eateries add to the convenience of staying in this area, allowing visitors to experience the local culture and cuisine.

For those seeking outdoor activities, the nearby Appalachian Trail provides excellent hiking opportunities, and many rentals are close to scenic trails that lead through the beautiful Connecticut countryside.
Where are the best Lakeville ski resort rentals?
For renting ski resort accommodations near Lakeville, Connecticut, the closest skiing options are found at the nearby Mohawk Mountain Ski Area, located just a short drive away. In Lakeville itself, visitors can find a range of charming cabins and lodges that provide a cozy atmosphere for winter getaways. Many properties in this area come equipped with essential amenities such as fully stocked kitchens, comfortable seating areas, and sometimes even fireplaces, superb for warming up after a day on the slopes.

Additionally, the nearby town of Salisbury offers further rental options, with historic homes and modern chalets that often feature amenities like hot tubs, outdoor patios, and ample space for families or groups. Being in the Litchfield Hills, Lakeville provides access to stunning winter landscapes, and guests can also enjoy local attractions, including quaint shops and delightful eateries, enhancing the overall experience.

For those looking to explore the outdoors beyond skiing, the surrounding areas offer opportunities for snowshoeing and winter hiking, with picturesque trails and scenic views of the snowy landscape.
What is the most popular type of holiday rental accomodation in Lakeville?
In Lakeville, holiday houses are the most popular type of holiday rental, with around 33 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the scenic beauty of the region. Additionally, there are several cottages and apartments that offer a more intimate setting, often equipped with cosy living areas and kitchen facilities to provide a comfortable home-away-from-home experience.
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 those seeking a memorable getaway. The area features charming properties located amidst picturesque surroundings, often equipped with spacious living areas and full kitchens, superb for preparing meals together. Many homes also include outdoor spaces, such as patios or gardens, where children can play and families can enjoy al fresco dining.

Visitors will appreciate the proximity to local attractions, including the scenic Lakeville Lake, which offers opportunities for swimming, fishing, and kayaking. Additionally, the nearby Salisbury and the surrounding Litchfield County provide ample hiking trails and opportunities for outdoor adventures.
Can I rent a holiday home with a pool or hot tub in Lakeville?
In Lakeville, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area, known for its charming lakes and scenic landscapes, provides a tranquil setting for relaxation. Many of these properties offer amenities such as private swimming pools, outdoor hot tubs, and spacious patios for enjoying the natural surroundings.
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 welcoming destination for travellers with pets. Many of these properties are situated in scenic locations, offering beautiful views of the surrounding countryside and access to outdoor spaces. Accommodations typically provide amenities such as fully equipped kitchens, spacious living areas, and private gardens, superb for relaxing after a day of exploring.

The area is known for its charming atmosphere, and visitors can enjoy nearby parks and trails that are ideal for walking dogs and enjoying nature. The picturesque Lake Wononscopomuc is also nearby, providing opportunities for water activities and leisurely strolls along the shore.
Are there any remote work holiday rentals in Lakeville?
In Lakeville, Connecticut, there are several options for remote work holiday rentals, with around 33 available in the area. These properties are well-suited for those looking to combine work and leisure, featuring amenities such as dedicated office spaces, desks, and reliable Wi-Fi, ensuring a productive environment. Many rentals also offer comfortable living spaces for relaxation after a day of work.

The scenic surroundings of Lakeville, including the picturesque Lake Wononscopomuc, provide a beautiful backdrop for breaks and outdoor activities. Visitors can enjoy nearby attractions, such as the hiking trails at the Mohawk State Forest or the charming local shops and restaurants in town. 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 rental amenities include fully equipped kitchens, allowing guests to prepare their meals at their convenience. Many properties also feature decks or patios, providing lovely outdoor spaces to enjoy the serene surroundings. A fireplace is a common amenity, adding a cozy touch for those cooler evenings. Additionally, rentals often come with coffee and tea makers, great for a warm beverage in the morning. Onsite parking is readily available, making it easy for visitors to explore the beautiful landscape of the area at their leisure.
When is the best time to visit Lakeville for a holiday rental?
The best time to book a holiday rental in Lakeville is during the peak summer months of June to August, when the area comes alive with vibrant outdoor activities and pleasant weather. Visitors flock to Lakeville for its picturesque landscapes and a range of activities, from kayaking on Lake Wononscopomuc to hiking the nearby trails, all while enjoying the warm temperatures that hover around the mid to high 20s Celsius.

July stands out as the most popular month for travellers, offering an ideal blend of lively events and opportunities to connect with nature. This month is great for travellers, as the delightful weather creates a friendly space for picnics, swimming, and exploring the charming local shops and eateries.

For those looking for a more budget-friendly option, consider visiting in December. While this month is quieter, it presents a unique charm with the winter scenery and festive decorations, making it an excellent time for cosy getaways or enjoying winter sports in the nearby areas.

Ultimately, your choice will depend on whether you prefer the bustling summer vibe filled with activities or the serene beauty of a winter retreat.
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.
What are the top attractions in Lakeville?
In Lakeville, Connecticut, visitors can enjoy a range of attractions that highlight the area's natural beauty and rich history. One of the most prominent spots is Lake Wononscopomuc, where outdoor enthusiasts can partake in activities like swimming, kayaking, and fishing. The surrounding landscape offers picturesque views, making it a great location for leisurely strolls or picnics.

The nearby Salisbury Central School hosts community events and is a focal point for local gatherings, while the historic Lakeville United Church of Christ adds to the charm of the neighbourhood. For those interested in history, the Lakeville Historical Society offers insights into the town's past and showcases local artefacts.

Additionally, the scenic Litchfield Hills region provides numerous hiking trails, including those found in the nearby Taconic State Park, great for exploring the natural surroundings.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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