Book Holiday Homes in Middlesex

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Featured Holiday Homes in Middlesex

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
Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country

Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country

Waterloo
When you stay at this vacation home in Waterloo, you'll be on the waterfront, within a 5-minute drive of National Memorial Day Museum and Muranda Cheese ...
Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country
creek's edge

creek's edge

Canandaigua
The price is AU$191 per night from 31 Dec to 1 Jan
AU$191
includes taxes & fees
31 Dec - 1 Jan 2025
Located in Canandaigua, this vacation home is within a 5-minute drive of Sonnenberg Gardens and Mansion State Historic Park and Canandaigua Motorsports ...
creek's edge
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Naples Valley Getaway!  Private home with hot tub.

Naples Valley Getaway! Private home with hot tub.

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.
Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to Wine trail

Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to Wine trail

Himrod
Located in Himrod, this vacation home is in a rural location, within a 15-minute walk of Shaw Vineyard and Hermann J. Wiemer Vineyard.
Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to Wine trail
Secluded home with large deck, foosball table, & W/D - near skiing

Secluded home with large deck, foosball table, & W/D - near skiing

Canandaigua
A stay at this vacation home places you in the heart of Canandaigua, within a 5-minute drive of UR Medicine - F.F. Thompson Hospital and Canandaigua Lake State ...
Secluded home with large deck, foosball table, & W/D - near skiing
Penn Yan House Rental - Close to Wineries!

Penn Yan House Rental - Close to Wineries!

Penn Yan
With a stay at this vacation home in Penn Yan, you'll be a 5-minute walk from Arts Center of Yates County and 8 minutes by foot from Oliver House Museum.
Penn Yan House Rental - Close to Wineries!
Pet-Friendly Ovid Home Near Seneca Lake & Wineries

Pet-Friendly Ovid Home Near Seneca Lake & Wineries

Ovid
Located in Ovid, this vacation home is a 2-minute drive from Sampson State Park and 9 minutes from Lodi Point State Park.
Pet-Friendly Ovid Home Near Seneca Lake & Wineries
Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

Geneva
With a stay at this vacation home in Geneva, you'll be within a 5-minute walk of South Main Street and Smith Center for the Arts.
Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.
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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
435 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$494
Popular accommodation
Retreat of falling waters, Direct Waterfront private house, NEW 40ft dock w/power, sleeps 8 in Wine Country, creek's edge, Naples Valley Getaway! Private home with hot tub. , Cozy Chateau cabin with hot tub, pool table, and view of Seneca Lake, close to Wine trail, Secluded home with large deck, foosball table, & W/D - near skiing, Penn Yan House Rental - Close to Wineries!, Pet-Friendly Ovid Home Near Seneca Lake & Wineries, Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

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$185 per night from 23 Dec to 24 Dec
AU$185
includes taxes & fees
23 Dec - 24 Dec
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$494 per night from 1 Jan to 2 Jan
AU$494
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Canandaigua, The Lake House on Canandaigua is on the boardwalk/promenade, within a 5-minute walk of Canandaigua City Pier and Canandaigua Lake State ...
The Lake House on Canandaigua
Comfort Inn & Suites Farmington - Victor

Comfort Inn & Suites Farmington - Victor

2.5 out of 5
6026 Route 96, Farmington, NY
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 5 Jan to 6 Jan
AU$166
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Comfort Inn & Suites Farmington - Victor places you in the heart of Farmington, a 2-minute drive from Finger Lakes Gaming and Racetrack and 6 minutes ...
Comfort Inn & Suites Farmington - Victor
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Hampton Inn Penn Yan

Hampton Inn Penn Yan

2.5 out of 5
110 Mace Street, Penn Yan, NY
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 29 Dec to 30 Dec
AU$131
includes taxes & fees
29 Dec - 30 Dec
With a 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
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.