Book Holiday Homes in Middlesex
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Featured Holiday Homes in Middlesex

The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!

Peaceful Hilltop Retreat Near Keuka Lake & Wine Trails

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

Fully Furnished Seneca Lake Lakefront Rental

Spacious Keuka Gem: BBQ, Firepit, Gameroom, Fireplace, and more

Keuka Glory-A beautiful home overlooking Keuka Lake!

Cozy All Season Bungalow right on the Lake wine and brewery trail.

Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK
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 | 689 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | The bungalow @ T. Spex Eyewear is a cozy, convenient stay in Canandaigua!, Peaceful Hilltop Retreat Near Keuka Lake & Wine Trails, 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, Fully Furnished Seneca Lake Lakefront Rental, Spacious Keuka Gem: BBQ, Firepit, Gameroom, Fireplace, and more, Keuka Glory-A beautiful home overlooking Keuka Lake!, Cozy All Season Bungalow right on the Lake wine and brewery trail., Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK |
Holiday Homes in Middlesex
Top Locations for Holiday Homes in Middlesex
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Top trending hotels in Middlesex

41 Lakefront Hotel, Trademark Collection By Wyndham

The Lake House on Canandaigua

Days Inn by Wyndham Geneva/Finger Lakes

Microtel Inn & Suites by Wyndham Geneva
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Top picks
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^Subject to availability and chosen travel dates.