Lakeville holiday homes

We found 166 holiday rentals — enter your dates for availability
Discover a selection of 15 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:18 Dec - 25 Dec

Interior
Living area
Room
Living area
Exceptional
(7 reviews)

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Goshen

8% off
NZ$5,761
for 7 nights, 1 home
NZ$823 per night
includes taxes & fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Entry foyer
kitchen island w/reclaimed wood
Our home sweet home!
Swing on our porch!
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

8% off
NZ$6,972
for 7 nights, 1 home
NZ$996 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE
Exterior
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
NZ$11,365
for 7 nights, 1 home
NZ$1,624 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Room
Outdoor dining
Dining
Private kitchen
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
NZ$5,095
for 7 nights, 1 home
NZ$728 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Private kitchen
Living area
Bathroom
Room
Wonderful
(36 reviews)

Two Bedroom Cottage Close To Town

Sharon

5% off
NZ$3,953
for 7 nights, 1 cottage
NZ$565 per night
includes taxes & fees
Two Bedroom Cottage Close To Town
After a day in the snow
Property grounds
We highly recommend the Sauna
Property grounds
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
NZ$4,322
for 7 nights, 1 home
NZ$617 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Interior
Living area
Living area
Living area
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
NZ$8,493
for 7 nights, 1 home
NZ$1,213 per night
includes taxes & fees
The Race Mountain House
dining room
Front Entrance
Interior
Interior
Exceptional
(15 reviews)

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield

8% off
NZ$7,518
for 7 nights, 1 home
NZ$1,074 per night
includes taxes & fees
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Friendly Lakeville will entice you

Enjoy the museums and other features of Lakeville. Travellers appreciate the restaurants in this welcoming city. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Lakeville

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

  • Mohawk Mountain Ski Area (11.1 mi / 17.9 km)
  • Catamount Ski Area (14.1 mi / 22.7 km)
  • Millbrook Vineyards and Winery (15.3 mi / 24.6 km)
  • Lake Taghkanic State Park (16.2 mi / 26 km)
  • Ski Butternut (16.3 mi / 26.2 km)
  • Sunset Meadow Vineyards (16.7 mi / 26.9 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:

  • 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)
  • 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Lakeville holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Lakeville holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Lakeville holiday homes?
You can find great discounts on holiday homes in Lakeville on Bookabach, 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.
Can I change or cancel my Lakeville holiday home booking on Bookabach?
To find Lakeville holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Lakeville?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Lakeville holiday home?
Book your Lakeville holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Lakeville?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Lakeville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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