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Featured Cottages in Winsted

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Plymouth
Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Private Island - Largest Fresh Water Reservoir in Mass....

Private Island - Largest Fresh Water Reservoir in Mass....

Otis
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.
Private Island - Largest Fresh Water Reservoir in Mass....
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.
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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 steps from Otis Reservoir and a 3-minute drive from Larkum Pond.
East Otis Vacation Rental w/ Private Deck & BBQ!
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Bethlehem
When you stay at this cottage in Bethlehem, you'll be on a lake, within a 5-minute drive of Bellamy-Ferriday House and Garden and Old Bethlehem Historical Society ...
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
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
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!
Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Becket
Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 6 minutes from October Mountain State Forest.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Perfect Vacation Get Away - Historical New Marlborough

Perfect Vacation Get Away - Historical New Marlborough

New Marlborough
Located in Great Barrington, this cottage is in a rural location, a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.
Perfect Vacation Get Away - Historical New Marlborough
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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
75 Cottages
Lowest Price
AU$210
Highest Price
AU$385
Popular accommodation
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape, Private Island - Largest Fresh Water Reservoir in Mass...., Idillic summer getaway in Litchfield Hills, CT., East Otis Vacation Rental w/ Private Deck & BBQ!, Lakeview property in private community. Lake & beach access. Swim/Kayak all day!, Cozy 2-bedroom Cottage with Access to Bantam Lake, West Cornwall Cabin ~ 4 Mi to Covered Bridge!, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Perfect Vacation Get Away - Historical New Marlborough

Top trending hotels in Winsted

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$210 per night from 28 Dec to 29 Dec
AU$210
includes taxes & fees
28 Dec - 29 Dec
With a stay at The Farmington Inn & Suites in Farmington, you'll be in the historical district, within a 15-minute drive of XL Center and Farmington Historic ...
The Farmington Inn & Suites
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel

Holiday Inn Express & Suites Bradley Airport, an IHG Hotel

2.5 out of 5
600 Spring St, Windsor Locks, CT
Fully refundable
The price is AU$225 per night from 25 Dec to 26 Dec
AU$225
includes taxes & fees
25 Dec - 26 Dec
When you stay at Holiday Inn Express & Suites Bradley Airport, an IHG Hotel in Windsor Locks, you'll be near the airport, within a 5-minute drive of Farmington ...
Holiday Inn Express & Suites Bradley Airport, an IHG Hotel
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
The price is AU$385 per night from 24 Dec to 25 Dec
AU$385
includes taxes & fees
24 Dec - 25 Dec
Located in Windsor Locks, Sheraton Hartford Hotel at Bradley Airport is connected to the airport, a 5-minute drive from Farmington River and 6 minutes from New ...
Sheraton Hartford Hotel at Bradley Airport
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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$233 per night from 30 Dec to 31 Dec
AU$233
includes taxes & fees
30 Dec - 31 Dec
With a stay at DoubleTree by Hilton Hartford - Bradley Airport in Windsor Locks, you'll be near the airport, within a 15-minute drive of XL Center and Broad ...
DoubleTree by Hilton Hartford - Bradley Airport
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See all available properties in Winsted
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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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^Subject to availability and chosen travel dates.