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Featured Winsted Cottages

The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

$362 nightly
The price is $404 total per night
$404 total
Oct 5 - Oct 6
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Free WiFi
Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Two Bedroom Cottage Close To Town

Two Bedroom Cottage Close To Town

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Cottage at Highland Lake, year-round, waterfront with a boat dock

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Idillic summer getaway in Litchfield Hills, CT.

Idillic summer getaway in Litchfield Hills, CT.

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lakefront Tranquility/Fishermans Delight

Lakefront Tranquility/Fishermans Delight

Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Charming, private 2-bedroom cottage on classic New England farm in Washington CT

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Light-filled cottage

Light-filled cottage

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Cozy 2-bedroom Cottage with Access to Bantam Lake

Cozy 2-bedroom Cottage with Access to Bantam Lake

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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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.

Hotel Options in Winsted

    DoubleTree by Hilton Hartford - Bradley Airport

    DoubleTree by Hilton Hartford - Bradley Airport

    16 Ella T. Grasso Turnpike, Windsor Locks, CT
    $127 nightly
    The price is $146 total per night from Oct 26 to Oct 27
    $146 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)
    Extended Stay America Suites Hartford Farmington

    Extended Stay America Suites Hartford Farmington

    1 Batterson Park Rd, Farmington, CT
    $102 nightly
    The price is $117 total per night from Nov 2 to Nov 3
    $117 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (1,004 reviews)
    Holiday Inn Express & Suites Bradley Airport by IHG

    Holiday Inn Express & Suites Bradley Airport by IHG

    600 Spring St, Windsor Locks, CT
    $105 nightly
    The price is $121 total per night from Oct 27 to Oct 28
    $121 total
    Oct 27 - Oct 28
    Total with taxes and fees
    8.8/10 Excellent! (1,133 reviews)

Cottages

Book a cottage in Winsted
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winsted. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winsted better.

Cottage apartments in Winsted range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winsted
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winsted and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winsted cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winsted. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winsted Cottages essential information

Accommodation
79 Cottages
Lowest Price
$117
Highest Price
$404
Popular accommodation
The Blue Elm - A Historic Berkshire Cottage, Summer Lake Cottage, private beach, Berkshire Hills, small village, Two Bedroom Cottage Close To Town, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Idillic summer getaway in Litchfield Hills, CT., Lakefront Tranquility/Fishermans Delight, Charming, private 2-bedroom cottage on classic New England farm in Washington CT, Light-filled cottage, Cozy 2-bedroom Cottage with Access to Bantam Lake