Rent Luxury Holiday Cottages in Connecticut

We selected the 60 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Connecticut

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.

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.

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment.

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.


We selected the top 3% holiday homes in Connecticut Cottages

Explore the 60 most perfect homes in our collection

View on map

Most popular homes in Connecticut

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

Country Escape

Country Escape

  • 5 guests

  • 2 bedrooms

Hunter, Greene County

View all

Check upcoming rates & availability for Connecticut Cottages


Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Connecticut. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Connecticut Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

Search our collection