Book Holiday Homes in Middlefield
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Featured Holiday Homes in Middlefield

McAngel Haven: 5 mins from Yale

Amazing Lakefront Property

NEW-Another Fun Downtown Location 1st floor

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Near Yale with Game Room

Family Stays: Middletown, CT

Beautiful 3BR, Rare Find, Clean & Guest Favorite

Enjoy a taste of New England in Historic Guilford Ct
Middlefield 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 Middlefield vacation homes are the perfect way for you to wing it.
Holiday houses in Middlefield 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 Middlefield 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 Middlefield adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middlefield 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 Middlefield 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.
Middlefield Holiday Homes essential information
Accommodation | 263 Holiday Homes |
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Lowest Price | NZ$181 |
Highest Price | NZ$1,982 |
Popular accommodation | McAngel Haven: 5 mins from Yale, Amazing Lakefront Property, NEW-Another Fun Downtown Location 1st floor, New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown., Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck., Near Yale with Game Room, Family Stays: Middletown, CT, Beautiful 3BR, Rare Find, Clean & Guest Favorite, Enjoy a taste of New England in Historic Guilford Ct |
More accommodations in Middlefield
Top trending hotels in Middlefield
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New Haven Hotel
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Omni New Haven Hotel at Yale

The Capitol Hotel, Ascend Hotel Collection

Cambria Hotel New Haven University Area
More ways to explore Middlefield
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^Subject to availability and chosen travel dates.