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Featured Cottages in Winsted

Quiet rustic cottage with shared lake access

Quiet rustic cottage with shared lake access

New Marlborough
With a stay at this cottage in Great Barrington, you'll be on a lake, just steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Quiet rustic cottage with shared lake access
Two Bedroom Cottage Close To Town

Two Bedroom Cottage Close To Town

Sharon
Located in Sharon, this cottage is a 4-minute drive from Bodhi Tree Gallery and 7 minutes from TriArts Sharon Playhouse.
Two Bedroom Cottage Close To Town
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough
Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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The Cottage at Highland Lake, year-round, waterfront with a boat dock

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

Winsted
With a stay at this cottage in Winsted, you'll be on the waterfront, just steps from Highland Lake and a 2-minute drive from Winchester Historical Society.
The Cottage at Highland Lake, year-round, waterfront with a boat dock
East Otis Vacation Rental w/ Private Deck & BBQ!

East Otis Vacation Rental w/ Private Deck & BBQ!

East Otis
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 3-minute drive from Larkum Pond.
East Otis Vacation Rental w/ Private Deck & BBQ!
Idillic summer getaway in Litchfield Hills, CT.

Idillic summer getaway in Litchfield Hills, CT.

Sharon
When you stay at this cottage in Sharon, you'll be on a river, within a 5-minute drive of Housatonic Meadows State Park and West Cornwall Covered Bridge.
Idillic summer getaway in Litchfield Hills, CT.
Cozy 2-bedroom Cottage with Access to Bantam Lake

Cozy 2-bedroom Cottage with Access to Bantam Lake

Morris
With a stay at this cottage in Morris, you'll be on a lake, just steps from Bantam Lake and a 2-minute drive from Camp Columbia State Park.
Cozy 2-bedroom Cottage with Access to Bantam Lake
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey
With a stay at this cottage in Monterey, you'll be within a 10-minute drive of Bidwell House Museum and Ashintully Gardens.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
West Cornwall Cabin ~ 4 Mi to Covered Bridge!

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3 out of 5
West Cornwall
Located in Cornwall, this cottage is within a 5-minute drive of Mohawk Mountain State Forest and Mohawk Mountain State Park.
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
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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.

Winsted Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winsted will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winsted definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winsted, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winsted Cottages essential information

Accommodation
87 Cottages
Lowest Price
AU$224
Highest Price
AU$593
Popular accommodation
Quiet rustic cottage with shared lake access, Two Bedroom Cottage Close To Town, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , The Cottage at Highland Lake, year-round, waterfront with a boat dock , East Otis Vacation Rental w/ Private Deck & BBQ!, Idillic summer getaway in Litchfield Hills, CT., Cozy 2-bedroom Cottage with Access to Bantam Lake, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks, West Cornwall Cabin ~ 4 Mi to Covered Bridge!

Top trending hotels in Winsted

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

2.5 out of 5
600 Spring St, Windsor Locks, CT
Fully refundable
The price is AU$224 per night from 6 Apr to 7 Apr
AU$224
includes taxes & fees
6 Apr - 7 Apr
When you stay at Holiday Inn Express & Suites Bradley Airport by IHG in Windsor Locks, you'll be near the airport and 5 minutes by car from Connecticut ...
Holiday Inn Express & Suites Bradley Airport by IHG
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 19 Apr to 20 Apr
AU$237
includes taxes & fees
19 Apr - 20 Apr
When you stay at The Farmington Inn & Suites in Farmington, you'll be in the historical district, within a 15-minute drive of XL Center and Connecticut Convention ...
The Farmington Inn & Suites
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 19 Apr to 20 Apr
AU$235
includes taxes & fees
19 Apr - 20 Apr
When you stay at DoubleTree by Hilton Hartford - Bradley Airport in Windsor Locks, you'll be near the airport, within a 15-minute drive of Connecticut Convention ...
DoubleTree by Hilton Hartford - Bradley Airport
Save an average of 15% on thousands of hotels when you're signed in
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road, West Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$593 per night from 20 Apr to 21 Apr
AU$593
includes taxes & fees
20 Apr - 21 Apr
When you stay at Delamar West Hartford in West Hartford, you'll be in a shopping district, within a 10-minute drive of XL Center and Connecticut Convention ...
Delamar West Hartford
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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.

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