Photo by Matthew Jay

Middlesex holiday homes

We found 483 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Middlesex that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, 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 – Middlesex

Showing deals for:25 Dec - 1 Jan

living room sofa sectional
waterfront view; upper patio for owner
front porch lake view sunny
dining room detail
Exceptional
(42 reviews)

Canandaigua Lake Farmhouse

Canandaigua

7% off
NZ$11,084
for 7 nights, 1 home
NZ$1,583 per night
includes taxes & fees
Canandaigua Lake Farmhouse
Banquet hall
View from Maids Quarters
Koi Pond Sitting Area
Sunroom w/gas fireplace
Exceptional
(30 reviews)

Secluded European Style 1810 Mansion minutes to the lake, sleeps 15

Canandaigua

8% off
NZ$14,793
for 7 nights, 1 home
NZ$2,113 per night
includes taxes & fees
Secluded European Style 1810 Mansion minutes to the lake, sleeps 15
Fully stocked kitchen
Interior
Grill on back deck for outdoor cooking.
Vinyl waterproof flooring in the kitchen.
Exceptional
(151 reviews)

Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes

Branchport

8% off
NZ$1,338
for 7 nights, 1 cabin
NZ$191 per night
includes taxes & fees
Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes
bathroom down
Southside porch
bedroom down east facing
den area
Exceptional
(5 reviews)

Charming 4-bedroom house with WiFi and AC in Branchport

Branchport

8% off
NZ$12,597
for 7 nights, 1 home
NZ$1,800 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in Branchport
Living area
Exterior
New railing summer 2024: now allows for total waterfront views-
Private kitchen
Exceptional
(14 reviews)

Lake House Retreat on Beautiful Canandaigua Lake Sleeps 12

Middlesex

7% off
NZ$16,886
for 7 nights, 1 cottage
NZ$2,412 per night
includes taxes & fees
Lake House Retreat on Beautiful Canandaigua Lake Sleeps 12
Private kitchen
Property grounds
Living area
Beautiful sight at sunset!
Exceptional
(49 reviews)

Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23

Penn Yan

7% off
NZ$6,048
for 7 nights, 1 home
NZ$864 per night
includes taxes & fees
Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23
coat hooks in garage entry
Spacious living room
Large kitchen island
Enjoy the campfire
Exceptional
(200 reviews)

Friends And Family Farmhouse

Penn Yan

8% off
NZ$7,211
for 7 nights, 1 home
NZ$1,030 per night
includes taxes & fees
Friends And Family Farmhouse
Downstairs bedroom
View from the living room
Exterior
Overhead view of the living room
Exceptional
(167 reviews)

Chalet overlooking Keuka Lake in the heart of Wine Country

Penn Yan

15% off
NZ$1,688
for 7 nights, 1 chalet
NZ$241 per night
includes taxes & fees
Chalet overlooking Keuka Lake in the heart of Wine Country
Exterior
Private kitchen
Dining
Living area
Exceptional
(11 reviews)

Beautiful and Secluded getaway on 10 acres

Canandaigua

8% off
NZ$6,488
for 7 nights, 1 home
NZ$927 per night
includes taxes & fees
Beautiful and Secluded getaway on 10 acres
Entrance across the street to the road that takes you to the community center
Balcony off of living room
Private kitchen
Interior
Exceptional
(37 reviews)

Waterfront two story condo

Canandaigua

8% off
NZ$4,272
for 7 nights, 1 apartment
NZ$610 per night
includes taxes & fees
Waterfront two story condo
Eat-In Kitchen
View from Covered Patio
Eat-In Kitchen with Views of Lake
Bedroom 2 with Queen Bed
Exceptional
(68 reviews)

Remodeled Lake House

Honeoye

8% off
NZ$2,375
for 7 nights, 1 cottage
NZ$339 per night
includes taxes & fees
Remodeled Lake House
Living area
Outdoor dining
Dining
Living area
Exceptional
(10 reviews)

Robust vacation home near wineries, nature and ski mountains in the FLX region!

Naples

8% off
NZ$6,031
for 7 nights, 1 home
NZ$862 per night
includes taxes & fees
Robust vacation home near wineries, nature and ski mountains in the FLX region!
Exterior
Dining
Private kitchen
Room
Exceptional
(40 reviews)

Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger

Canandaigua

8% off
NZ$7,102
for 7 nights, 1 home
NZ$1,015 per night
includes taxes & fees
Enjoy Cabin Vibes & Lake Views, Close to Town, Lake & FLX Activities; EV Charger
Eat-In Kitchen
A Short Walk to the Water and Dock
Enclosed Porch Showing View of Lake at End of Street
Front of House
Exceptional
(113 reviews)

Remodeled House...Steps away from Honeoye Lake

Honeoye

8% off
NZ$2,375
for 7 nights, 1 home
NZ$339 per night
includes taxes & fees
Remodeled House...Steps away from Honeoye Lake
Lower level.
Kitchen Area with stainless appliances.
Eat-in Kitchen
Roku TV in Living Room
Exceptional
(18 reviews)

"Come Sail Away" A charming place in Canandaigua designed with a sailing theme.

Canandaigua

9% off
NZ$3,639
for 7 nights, 1 home
NZ$520 per night
includes taxes & fees
"Come Sail Away" A charming place in Canandaigua designed with a sailing theme.
Private kitchen
Large living room with 18’ ceiling.
Room
Open floor plan in living room and kitchen.
Exceptional
(58 reviews)

Renovated Cabin, with custom craftwork, in Picturesque Finger Lakes Wine Country

Branchport

8% off
NZ$1,572
for 7 nights, 1 cabin
NZ$225 per night
includes taxes & fees
Renovated Cabin, with custom craftwork, in Picturesque Finger Lakes Wine Country
Room
Property grounds
Living area
Private kitchen
Exceptional
(24 reviews)

Tranquil creek side retreat

Canandaigua

8% off
NZ$1,650
for 7 nights, 1 apartment
NZ$236 per night
includes taxes & fees
Tranquil creek side retreat
Convertible sofa turns into full size bed
Memory comfort mattress. Protective allergen covers. Organic cotton bed linens.
Living area
Smart tv, Wi-Fi, Live tv streaming app, books & games
Exceptional
(58 reviews)

LE PETIT - 5 min. Walk to Lake Resort or Downtown

Canandaigua

8% off
NZ$3,343
for 7 nights, 1 apartment
NZ$478 per night
includes taxes & fees
LE PETIT - 5 min. Walk to Lake Resort or Downtown
Exterior
Living area
Living area
Private kitchen
Exceptional
(20 reviews)

Lakeside 2 bdrm Apartment steps from lake. Private Beach and Park

Honeoye

8% off
NZ$2,466
for 7 nights, 1 apartment
NZ$352 per night
includes taxes & fees
Lakeside 2 bdrm Apartment steps from lake. Private Beach and Park

  • 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

Explore the natural setting in Middlesex

Learn about the unique charm of Middlesex with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Middlesex

Are you hoping to discover attractions to see while you're in town? Venture out of your cosy holiday rental and check out everything that Middlesex has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to appreciate the scenery, Middlesex is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Canandaigua Lake (5.4 mi / 8.7 km)
  • Keuka Lake State Park (11 mi / 17.8 km)
  • Kershaw Park (11.7 mi / 18.9 km)
  • Honeoye Lake (12.8 mi / 20.7 km)
  • Sonnenberg Gardens and Mansion State Historic Park (13.3 mi / 21.4 km)
  • Keuka Lake Outlet Trail (14.2 mi / 22.8 km)

Frequently asked questions

What is the best area to stay in Middlesex when booking a holiday rental?
When considering a holiday rental in Middlesex, New York, the area around the charming Finger Lakes region stands out as an excellent choice. This picturesque region is renowned for its stunning lakes, rolling hills, and vibrant wineries. Staying in this area offers a delightful combination of natural beauty and local attractions.One of the top draws is the nearby Canandaigua Lake, great for outdoor enthusiasts looking to enjoy activities such as boating, fishing, or simply soaking in the serene views. Additionally, the region boasts several wineries and vineyards, making it an ideal destination for those interested in wine tasting and culinary experiences.In terms of accommodation, Middlesex has a variety of properties available, ranging from cosy cottages to larger family homes, suiting different preferences and group sizes.
Where are the best areas for renting a beach house in Middlesex?
For renting a beach house in Middlesex, the area around Canandaigua Lake is highly recommended. This picturesque lake is known for its stunning views and recreational opportunities, making it a popular destination for travellers seeking a lakeside getaway. Properties near the western shore often offer direct access to the water, with many houses featuring private docks, outdoor decks, and fire pits, superb for enjoying warm evenings by the lake.In the vicinity of the town of Middlesex, visitors can find charming cottages and larger family homes that come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and sometimes even games rooms, suiting families or groups looking to relax and enjoy the outdoors. Some rentals may also provide kayaks or paddleboards, enabling guests to explore the serene waters of Canandaigua Lake.Additionally, the nearby town of Naples offers a quaint atmosphere with local shops and eateries, enhancing the overall experience for those renting in the area.
Where are the best Middlesex ski resort rentals?
For skiing in Middlesex, the nearest resort is located at Bristol Mountain, just a short drive away. To find suitable holiday rentals, travellers should consider accommodations in the quaint nearby village of Bristol. Here, visitors can expect a variety of properties, including cosy cabins and charming lodges that often feature essential amenities such as fully equipped kitchens, wood-burning stoves, and outdoor decks great for enjoying the snowy scenery.In the town of Canandaigua, situated a little further from the slopes, there are also rental options that include lakeside homes and modern apartments. Many of these properties come with conveniences like Wi-Fi, laundry facilities, and access to recreational activities, making them ideal for families or groups. The proximity to Canandaigua Lake adds an additional appeal, providing opportunities for winter hikes or picturesque views.Moreover, the area boasts access to several local restaurants and shops, enhancing the overall experience for travellers.
What is the most popular type of holiday rental accomodation in Middlesex?
In Middlesex, holiday houses are the most popular type of holiday rental, with around 22 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas ideal for enjoying the scenic surroundings. Additionally, there are about 14 cottages that provide a charming, rustic experience, often set in picturesque locations, superb for couples or small families looking for a peaceful retreat. Several cabins are also offered, adding to the variety of options for travellers seeking a cozy escape in this beautiful part of New York.
Are there any family house rentals in Middlesex?
In Middlesex, New York, there are around 15 family-friendly house rentals available, making it a suitable destination for groups travelling together. The area is surrounded by the picturesque Finger Lakes region, known for its stunning landscapes and numerous outdoor activities. Many of these properties provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.Visitors can take advantage of the nearby attractions, such as the beautiful Canandaigua Lake, which offers opportunities for swimming, boating, and hiking in the surrounding trails. Additionally, the local wineries and charming small towns create a great atmosphere for family outings.
Can I rent a holiday home with a pool or hot tub in Middlesex?
In Middlesex, New York, there are several holiday homes available for rent that feature pools or hot tubs. This picturesque area, located near the shores of Canandaigua Lake, offers a peaceful retreat for travellers looking to unwind. Many of the rentals come equipped with private pools and hot tubs, alongside amenities such as spacious outdoor decks, full kitchens for self-catering, and comfortable living areas great for family gatherings.The neighbourhoods around the lake provide scenic views and easy access to local attractions such as hiking trails and wineries, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Middlesex?
In Middlesex, there are pet-friendly house rentals available, offering a great selection for travellers who wish to bring their furry companions along. The area is known for its beautiful landscapes, including stunning views of Canandaigua Lake. Many of the holiday homes in this region come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios, ideal for enjoying the scenic surroundings.Additionally, the vicinity offers a range of outdoor activities, making it a great destination for pet owners. Nearby parks and trails provide opportunities for hiking and leisurely walks with pets, ensuring plenty of fresh air and exploration.
Are there any remote work holiday rentals in Middlesex?
In Middlesex, New York, there are around 30 holiday rentals that cater to remote work needs, making it an ideal destination for those looking to blend work and leisure. Many properties come equipped with reliable Wi-Fi, ensuring a smooth work experience. You'll find accommodations featuring dedicated workspaces or desks, providing a comfortable environment for productivity. Additionally, amenities like free Wi-Fi in rooms, as well as other conveniences, allow guests to stay connected while enjoying the beauty of the Finger Lakes region.Middlesex is surrounded by picturesque landscapes, including nearby vineyards and lakes, superb for unwinding after a day of work. The area also offers opportunities for outdoor activities such as hiking and boating, allowing guests to enjoy nature during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Middlesex?
In Middlesex, popular holiday rentals typically come equipped with essential amenities that enhance the comfort of your stay. Most accommodations feature a fully equipped kitchen, allowing guests to prepare their own meals, which is particularly convenient for families or those looking to save on dining expenses. Additionally, many rentals offer onsite parking, making it easy for visitors to explore the surrounding areas.For guests who enjoy cooking, amenities like blenders may be available, enabling the preparation of smoothies or other blended foods. Many properties also include a fireplace, providing a warm and inviting atmosphere during cooler evenings, great for relaxation after a day of exploring. Furthermore, outdoor spaces such as decks or patios are common, offering guests an opportunity to enjoy the beautiful scenery of the Finger Lakes region while unwinding outdoors.
What are the top attractions in Middlesex?
In Middlesex, New York, visitors can enjoy a range of attractions that highlight the area's natural beauty and local culture. The scenic Canandaigua Lake is a major draw, offering opportunities for boating, fishing, and hiking along its picturesque shores. The nearby Finger Lakes Wine Country is renowned for its vineyards and wineries, where travellers can indulge in tastings and tours, often set in stunning landscapes.For those interested in outdoor activities, the surrounding Finger Lakes National Forest provides miles of hiking trails and beautiful views, great for exploring the region's diverse flora and fauna. Additionally, the quaint village of Naples, just a short drive away, is famous for its annual Grape Festival and charming shops, allowing visitors to experience local craftsmanship and delicacies.Art enthusiasts might want to visit the nearby town of Canandaigua, which features the CMAC (Constellation Brands-Marvin Sands Performing Arts Centre), hosting live music and performances throughout the summer.
Are all fees included in the Middlesex 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 Middlesex holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Middlesex 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 Middlesex holiday homes?
You can find great discounts on holiday homes in Middlesex 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 Middlesex holiday home booking on Bookabach?
To find Middlesex 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 Middlesex?
A long-stay holiday home in Middlesex 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 Middlesex holiday home?
Book your Middlesex 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 Middlesex?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Middlesex 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.