Book Holiday Homes in Middlesex

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Featured Holiday Homes in Middlesex

Lakefront Home in the heart of Seneca Lake Wine Trail

Lakefront Home in the heart of Seneca Lake Wine Trail

Himrod
Located in Himrod, this vacation home is a 5-minute drive from Shaw Vineyard and 5 minutes from Hermann J. Wiemer Vineyard.
Lakefront Home in the heart of Seneca Lake Wine Trail
Retreat of falling waters

Retreat of falling waters

Naples
When you stay at this vacation home in Naples, you'll be on a river, within a 5-minute drive of Naples Community Park Disc Golf Course and Clarks Gully.
Retreat of falling waters
Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain

Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain

Naples
Located in Naples, this vacation home is in a rural location, within a 5-minute drive of Reservoir Creek Golf Course and Bristol Valley Theater.
Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain
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Peaceful, pet friendly and newly remodeled Geneva home

Peaceful, pet friendly and newly remodeled Geneva home

Geneva
The price is AU$476 per night from 3 Apr to 4 Apr
AU$476
includes taxes & fees
3 Apr - 4 Apr
With a stay at this vacation home in Geneva, you'll be within a 5-minute drive of Seneca Lake State Park and Smith Center for the Arts.
Peaceful, pet friendly and newly remodeled Geneva home
Charming Canandaigua Lake House w/ Deck & Views!

Charming Canandaigua Lake House w/ Deck & Views!

Canandaigua
Located in Canandaigua, this vacation home is in the mountains, a 1-minute drive from Canandaigua Lake and 6 minutes from Heron Hill Winery Tasting Room at ...
Charming Canandaigua Lake House w/ Deck & Views!
Croft Cove: laid back home on Lamoka Lake with private lakefront

Croft Cove: laid back home on Lamoka Lake with private lakefront

Bradford
Located in Bradford, this vacation home is on the waterfront, a 1-minute drive from Lamoka Lake and 6 minutes from Waneta Lake.
Croft Cove: laid back home on Lamoka Lake with private lakefront
Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK

Dresden
With a stay at this vacation home in Dresden, you'll be on the waterfront, within a 15-minute drive of Keuka Lake and Prejean Winery.
Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK
Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!

Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!

Himrod
Located in Himrod, this vacation home is on the waterfront, within a 10-minute drive of Shaw Vineyard and Hermann J. Wiemer Vineyard.
Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!
Townhouse with Lake views/access, 10 min to ski Bristol Mountain

Townhouse with Lake views/access, 10 min to ski Bristol Mountain

Canandaigua
The price is AU$431 per night from 3 Apr to 4 Apr
AU$431
includes taxes & fees
3 Apr - 4 Apr
Located in Canandaigua, this vacation home is on a lake, within a 5-minute drive of Canandaigua Lake and Heron Hill Winery Tasting Room at Bristol.
Townhouse with Lake views/access, 10 min to ski Bristol Mountain
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Middlesex Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middlesex vacation homes are the perfect way for you to wing it.

Holiday houses in Middlesex let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middlesex in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middlesex adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middlesex with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middlesex vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middlesex Holiday Homes essential information

Accommodation
626 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$490
Popular accommodation
Lakefront Home in the heart of Seneca Lake Wine Trail, Retreat of falling waters, Naples Valley Getaway! Private home with hot tub- 20 min. From Bristol Mountain, Peaceful, pet friendly and newly remodeled Geneva home, Charming Canandaigua Lake House w/ Deck & Views!, Croft Cove: laid back home on Lamoka Lake with private lakefront, Lake Dreamin-Seneca Lake-Waterfront-Hot Tub-Wine Trail, 100ft Private Level Beach-Pets OK, Plum Point Villa - Stunning View In The Heart Of The Finger Lakes!, Townhouse with Lake views/access, 10 min to ski Bristol Mountain

Top trending hotels in Middlesex

41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

3 out of 5
41 Lake Front Blvd, Geneva, NY
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 3 Apr to 4 Apr
AU$193
includes taxes & fees
3 Apr - 4 Apr
When you a stay at 41 Lakefront Hotel, Trademark Collection By Wyndham in Geneva, you'll be on a lake, just steps from South Main Street and Geneva Bark ...
41 Lakefront Hotel, Trademark Collection By Wyndham
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street, Canandaigua, NY
Fully refundableReserve now, pay when you stay
The price is AU$490 per night from 8 Apr to 9 Apr
AU$490
includes taxes & fees
8 Apr - 9 Apr
With a stay at The Lake House on Canandaigua in Canandaigua, you'll be on the boardwalk/promenade, within a 10-minute drive of CMAC Performing Arts Center and ...
The Lake House on Canandaigua
Hampton Inn Penn Yan

Hampton Inn Penn Yan

2.5 out of 5
110 Mace Street, Penn Yan, NY
The price is AU$148 per night from 20 Apr to 21 Apr
AU$148
includes taxes & fees
20 Apr - 21 Apr
When you stay at Hampton Inn Penn Yan in Penn Yan, you'll be in a state park, just steps from Keuka Lake and a 2-minute drive from Arts Center of Yates ...
Hampton Inn Penn Yan
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Holiday Inn Express Canandaigua - Finger Lakes by IHG

Holiday Inn Express Canandaigua - Finger Lakes by IHG

2.5 out of 5
330 Eastern Blvd., Canandaigua, NY
Fully refundable
The price is AU$165 per night from 20 Apr to 21 Apr
AU$165
includes taxes & fees
20 Apr - 21 Apr
With a stay at Holiday Inn Express Canandaigua - Finger Lakes by IHG in Canandaigua, you'll be within a 15-minute walk of Roseland Waterpark and Kershaw ...
Holiday Inn Express Canandaigua - Finger Lakes by IHG
Don't see what you're looking for?
See all available properties in Middlesex
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.