Connecticut Homes for a Hiking Trip

We selected the 126 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Connecticut

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock.

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Have you ever wanted your very own slice of the Catskills? Of course, you have.

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

Find your own slice of heaven in East Hampton with a stay in this impressive glasshouse. Surrounded by lush trees with beautiful views, this is the perfect setting for a restorative retreat or special family gathering.


We selected the top 3% holiday homes in Connecticut Homes for a Hiking Trip

Explore the 126 most perfect homes in our collection

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Most popular homes in Connecticut

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Firthcliffe, New York

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

The Great Harvest

The Great Harvest

  • 34 guests

  • 10 bedrooms

Coolbaugh Township, Monroe County

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Frequently asked questions

Explore our collection of homes for a hiking trip in Connecticut. They are perfect to relax in after a day of exploring the outdoors. They come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the most beautiful homes for a hiking trip in Connecticut. Our team of Plum Experts are on-hand 24/7 should you need anything.

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