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Middlesex vacation rentals

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Discover a selection of 11 homes and other vacation rentals in Middlesex that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Middlesex

Showing deals for:Aug 14 - Aug 21

Image gallery for Canandaigua Lake Farmhouse

West lake road front yard
9.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Canandaigua Lake Farmhouse

Canandaigua

8% off
Price is $806
$5,639 for 7 nights
All fees included
Canandaigua Lake Farmhouse

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Find out more about Middlesex

Why visit Middlesex

  • Stunning Natural Scenery: Enjoy breathtaking views of lakes and valleys in the picturesque Finger Lakes region.
  • Outdoor Adventures: Middlesex is perfect for hiking, boating, and other outdoor activities for nature lovers.
  • Romantic Getaways: The serene ambiance makes Middlesex an ideal destination for couples looking for a peaceful retreat.
  • Charming Accommodations: Choose from cozy vacation rentals, cottages, and rustic cabins to enhance your stay.
  • Friendly Locals: Experience the warm hospitality of Middlesex’s community while exploring nearby towns.

Popular types of accommodation in Middlesex

Discover the charm of Middlesex with a variety of vacation rentals to suit every traveler. From cozy houses to quaint cottages and rustic cabins, there's something for everyone. Whether you're seeking the perfect spot for a family getaway or a romantic retreat, our platform provides transparent information and helpful reviews on Middlesex hotels, motels, and rentals. Find your ideal accommodation in Middlesex County and enjoy a memorable stay.

  • Houses: Enjoy the comfort and space of a private vacation home, perfect for families or groups looking for a relaxing getaway in Middlesex.
  • Cottages: Experience the charm of cozy cottages, ideal for a quaint and peaceful retreat surrounded by nature.
  • Cabins: Escape to rustic cabins that provide a unique stay, often nestled in scenic areas for a true nature experience.
  • Apartments: Conveniently located apartments offer a home-like feel, making them suitable for shorter stays or couples.
  • Condos: Modern condos combine comfort and amenities, perfect for travelers seeking a stylish place to unwind.**

Top attractions near Middlesex

Middlesex, New York, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. The area boasts stunning scenery, with popular attractions including beautiful lakes, scenic state parks, and modern colleges. Whether you're looking for adventure or a peaceful retreat, Middlesex offers a variety of activities that cater to travelers eager to explore nature and enjoy the breathtaking landscapes.

  • Canandaigua Lake: Located 5 miles from Middlesex, Canandaigua Lake offers stunning beach areas and picturesque scenery, perfect for outdoor activities and romantic getaways. Enjoy swimming, picnicking, or simply soaking in the natural beauty.
  • Bristol Mountain Ski Resort: Just 8 miles from Middlesex, this ski resort is a haven for adventure seekers. Experience thrilling skiing and snowboarding on diverse slopes, all amidst breathtaking mountain landscapes.
  • Keuka Lake State Park: Situated 11 miles away, Keuka Lake State Park boasts beautiful vistas, hiking trails, and opportunities for outdoor recreation, making it an ideal spot for family outings and nature enthusiasts.

Things to do recommended for couples

For a romantic getaway in Middlesex, consider skiing at Bristol Mountain Ski Resort, only 8 miles away, or enjoy a delightful wine tasting at Heron Hill Winery, just 5 miles from town. If you're up for more adventure, Hunt Hollow ski field is a thrilling 11 miles away.

Things to do recommended for families

Your family will love exploring Ontario County Park at Gannett Hill for relaxation, splashing around at Roseland Waterpark for adventure, and enjoying the serene beauty of Grimes Glen. Each destination offers a unique experience just a short drive from Middlesex, perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Middlesex can enjoy a round of golf at Majestic Hills Golf Course, explore unique finds at the Windmill Farm & Craft Market, and experience captivating performances at the Bristol Valley Theater, creating memorable moments filled with outdoor fun, local crafts, and cultural entertainment.

*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 Middlesex

If you're traveling with a group, family, or pets, or if you're in search of extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middlesex with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Middlesex with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Middlesex: For many families, a vacation just isn't the same without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Middlesex: If you're in search of vacation rentals offering discounts 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Middlesex

Middlesex, New York, offers a charming blend of outdoor adventures and serene landscapes, perfect for romantic getaways or family-friendly vacations. Nestled in the picturesque Finger Lakes region, visitors can enjoy breathtaking valley views and a rural ambiance filled with friendly locals. Explore nearby towns for delightful scenery and a relaxing atmosphere, making Middlesex an ideal base for your unforgettable travel experience.

  • Canandaigua: Located 13 miles from Middlesex, Canandaigua is a charming city known for its stunning outdoor experiences and romantic scenery. Visitors flock to Canandaigua for its beautiful lake, which offers opportunities for boating and fishing. The nearby Canandaigua Lake State Park provides hiking trails and picnic areas, perfect for a day in nature. In the winter, the city transforms into a ski haven, attracting winter sports enthusiasts to its ski resorts and fields. The picturesque views and serene atmosphere make Canandaigua a must-visit destination for any traveler seeking relaxation and adventure.
  • Penn Yan: Just 12 miles from Middlesex, Penn Yan is a delightful city known for its scenic landscapes and outdoor adventures. The area is surrounded by lush greenery, making it ideal for hiking and exploring nature trails. Visitors can enjoy recreational areas that provide ample opportunities for outdoor activities. The proximity to Keuka Lake enhances the charm of Penn Yan, offering stunning views and water-related fun. With its inviting atmosphere and attractions like modern colleges and state parks, Penn Yan is a perfect spot for those looking for a picturesque getaway.
  • Rushville: Only 5 miles away from Middlesex, Rushville is a quaint city that offers a delightful mix of outdoor experiences and cultural attractions. Known for its scenic beauty, visitors can explore recreational areas and enjoy local music concerts and theater performances. The nearby lake and state park provide additional opportunities for hiking and water activities. Rushville’s friendly community vibe and picturesque surroundings make it an ideal location for tourists seeking both relaxation and cultural enrichment during their vacation.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial discounts. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy way to plan your travel. You can create new trips, continue from where you last stopped, or manage your travel plans all in one place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, and Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the natural setting in Middlesex

Learn about the unique charm of Middlesex with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Middlesex

Are you hoping to discover things to do while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Middlesex a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bristol Mountain Ski Resort (7.5 mi / 12 km)
  • Roseland Waterpark (12.2 mi / 19.6 km)
  • Ravines Wine Cellars on Seneca Lake (16.9 mi / 27.3 km)
  • Keuka Lake Vineyards (19.3 mi / 31.1 km)
  • Bully Hill Vineyards (19.4 mi / 31.2 km)
  • Three Brothers Wineries and Estates (19.6 mi / 31.5 km)

Exploring the natural features in Middlesex

Whether you're looking for fun outdoor activities or just want to take in the scenery, Middlesex is a great place to spend some time outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Canandaigua Lake (5.4 mi / 8.7 km)
  • Keuka Lake State Park (11 mi / 17.8 km)
  • Sonnenberg Gardens and Mansion State Historic Park (13.3 mi / 21.4 km)
  • Keuka Lake Outlet Trail (14.2 mi / 22.8 km)
  • Keuka Lake (16.2 mi / 26 km)
  • Seneca Lake (18.8 mi / 30.3 km)

Frequently asked questions

What is the best area to stay in Middlesex, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Middlesex, New York, the Finger Lakes region offers a charming escape with a variety of options. One of the standout neighborhoods is the area surrounding Canandaigua Lake, where you'll find stunning waterfront views and a tranquil atmosphere. This location is not only picturesque but also conveniently close to top attractions like the Sonnenberg Gardens and Mansion State Historic Park, which features beautiful gardens and a historic home to explore. Additionally, the region is known for its wineries, making it a great spot for wine enthusiasts seeking to sample local flavors.

Another appealing option is the quaint village of Naples, which is famous for its beautiful landscapes and proximity to the Naples Grape Festival. This small community provides a welcoming vibe, and visitors can enjoy outdoor activities, including hiking and fishing in the nearby parks.
How much does it cost to rent a vacation home in Middlesex?
Prices for vacation rentals in Middlesex 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 Middlesex 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 Middlesex vacation house rentals?
You can find great discounts on house rentals in Middlesex 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 Middlesex?
For renting a beach house in Middlesex, New York, travelers should consider the areas surrounding Canandaigua Lake, particularly the shoreline along the eastern side where the town is located. This region offers a variety of vacation rentals, ranging from cozy cottages to spacious homes with direct lake access. Many properties come equipped with amenities such as private docks, outdoor patios, and fire pits, providing a ideal setting for families or groups looking to enjoy lakefront living.

The nearby village of Canandaigua features popular points of interest, including local shops, restaurants, and the beautiful Kershaw Park, which offers sandy beaches and picnic areas. Rentals in this vicinity often include features like fully equipped kitchens and laundry facilities, making them ideal for longer stays.

Additionally, the surrounding Finger Lakes region is known for its wineries and scenic hiking trails. Properties in the area frequently provide easy access to local vineyards and nature reserves, with some accommodations boasting amenities like outdoor grills and access to biking trails.
Where are the best Middlesex ski resort rentals?
For skiing near Middlesex, New York, travelers should consider rentals in the nearby area of Canandaigua, which is approximately a 30-minute drive from the ski resorts at Bristol Mountain. In Canandaigua, visitors can find a variety of vacation rentals, including cozy cabins and spacious homes that often come equipped with amenities like fireplaces, full kitchens, and outdoor decks, great for relaxing after a day on the slopes.

Additionally, the town of Naples, situated closer to Bristol Mountain, offers charming properties that may include features such as hot tubs, scenic views of the surrounding hills, and proximity to local dining options. Many of these rentals cater to families and groups, providing ample space and comfort for a winter getaway.
What is the most popular type of vacation rental accomodation in Middlesex?
In Middlesex, vacation houses are the most popular type of accommodation, with about 11 available in the area. These houses typically offer spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups seeking comfort and convenience. Additionally, several cottages and cabins can be found, providing a more rustic and cozy atmosphere. These alternative options often come with charming details and are set in tranquil locations, superb for those looking to relax and enjoy the natural beauty of the region.
Are there any family house rentals in Middlesex?
In Middlesex, New York, families will find a selection of about 15 vacation homes that cater to their needs. This charming area, situated near the beautiful Finger Lakes region, offers properties with spacious living areas, fully equipped kitchens for family meals, and outdoor spaces for children to enjoy. Many homes come with amenities like Wi-Fi and air conditioning to enhance comfort during your stay.

Visitors will appreciate the proximity to local attractions such as Keuka Lake, where opportunities for swimming, boating, and picnicking abound. The surrounding countryside is superb for hiking and exploring, making Middlesex a wonderful choice for families seeking both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Middlesex?
In Middlesex, New York, travelers can find several vacation homes available for rent that feature pools and hot tubs. This picturesque area, located near the shores of Canandaigua Lake, offers a serene setting superb for relaxation. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas ideal for barbecues or family gatherings.

Properties often include well-appointed kitchens, comfortable living spaces, and amenities that enhance the vacation experience, such as Wi-Fi and air conditioning. Additionally, being close to the lake means guests can enjoy various water activities, hiking trails, and the natural beauty of the Finger Lakes region.
Can I find long-stay vacation rentals in Middlesex?
A long-stay vacation rental in Middlesex 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 Middlesex?
In Middlesex, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with pets. Vacation homes in this charming area often come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy fresh air. Many properties also feature conveniences like Wi-Fi and laundry facilities, ensuring a comfortable stay for families and groups.

Middlesex is located near beautiful natural attractions, including the stunning Finger Lakes region, which offers numerous outdoor activities and scenic views. Nearby parks and trails provide excellent opportunities for walks and hiking with pets.
Are there any remote work vacation rentals in Middlesex?
In Middlesex, New York, there are about 15 remote work vacation rentals available, making it a suitable destination for travelers looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desk spaces, and comfortable chairs. This allows guests to maintain productivity while enjoying the serene surroundings of the Finger Lakes region.

Travelers can expect a variety of accommodations, from cozy cabins to spacious homes, often featuring outdoor spaces for relaxation after a day of work. The natural beauty of the area, including nearby lakes and hiking trails, provides ample opportunities for outdoor activities during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middlesex vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middlesex 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 Middlesex?
In Middlesex, popular vacation rentals typically come equipped with a range of amenities to ensure a comfortable stay. Most properties feature a well-equipped kitchen, allowing guests to prepare their own meals. Onsite parking is another common amenity, providing convenience for travelers with vehicles. Many rentals also include a blender for those who enjoy making smoothies or cocktails. A fireplace is often part of the offerings, creating a cozy atmosphere during cooler evenings. Additionally, outdoor spaces like decks or patios are frequently available, providing a lovely spot for relaxation and enjoying the scenic surroundings.
How early should I book a Middlesex vacation rental?
Book your Middlesex 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 Middlesex, New York, United States of America?
In Middlesex, New York, visitors can explore a variety of attractions that highlight the region's natural beauty and recreational opportunities. The picturesque Canandaigua Lake, located nearby, offers opportunities for boating, fishing, and swimming, with several public access points and parks along its shores. The town is also close to the Finger Lakes Wine Country, where travelers can visit numerous vineyards and wineries, enjoying tastings and scenic views of the surrounding landscapes.

For outdoor enthusiasts, the nearby Finger Lakes National Forest provides hiking trails, camping options, and the chance to experience the area's diverse flora and fauna. The quaint downtown area of Middlesex features charming local shops and restaurants, providing a taste of the community's culture.
Can I change or cancel my Middlesex home rental booking on Vrbo?
To find Middlesex 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 Middlesex 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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