Holiday rentals in Winsted

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Top-rated holiday rentals in Winsted

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Guest favourite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

25 Feb – 4 Mar

£228 per night

Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 347 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

16–23 Aug

£358 per night

Guest favourite

Holiday home in Torrington

4.97 out of 5 average rating, 130 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

7–14 Jun

£152 per night

Guest favourite

Guest suite in Canaan

4.98 out of 5 average rating, 293 reviews

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

18–25 Nov

£132 per night

Guest favourite

Flat in Torrington

4.98 out of 5 average rating, 120 reviews

Apartment on Main St.

Hidden gem. Large combined living room/bedroom apt with separate kitchen and balcony. Private entrance. This is 1 unit in a 3 family house. 10 to 15 minutes walking distance to downtown shops, restaurants, Warner Theatre and Nutmeg Ballet. Shared huge garden, with Koi pond and pergola. Parking in the driveway for 1 car (possibly more, message for details). WiFi and Smart TV with some local channels (no cable). 45 minutes to Bradley Airport, 2 hours to NYC, 20 minutes to ski slopes.

25 May – 1 Jun

£122 per night

Guest favourite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

29 Apr – 6 May

£148 per night

Guest favourite

Guest suite in East Granby

4.84 out of 5 average rating, 273 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

30 Oct – 6 Nov

£91 per night

Guest favourite

Cabin in Colebrook

4.94 out of 5 average rating, 196 reviews

Adorable, storybook log cabin

Note to prospective guests: BEFORE REQUESTING TO BOOK, fill out your profile and explain the reason for your visit in your initial request. If you have plans to entertain in our cabin you must discuss it with us in advance of your booking. Fantastic, authentic log cabin on 7 acres of wooded land with a private pond and a sandy beach. Charm throughout with beds for nine to ten people.

23–30 Sept

£211 per night

Guest favourite

Guest house in Granby

4.99 out of 5 average rating, 703 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

1–8 Mar

£155 per night

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

13–20 Jan

£89 per night

Guest favourite

Cottage in Granby

4.87 out of 5 average rating, 137 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

26 Oct – 2 Nov

£146 per night

Guest favourite

Flat in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

7–14 Dec

£89 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Winsted holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winsted's top sights

Kent Pizza4 locals recommend

Mario's Tuscany Grill11 locals recommend

Stop & Shop8 locals recommend

R&B Sports World3 locals recommend

Little Red Barn Brewers5 locals recommend

Gilson Cinema & Cafe14 locals recommend

Other great holiday rentals in Winsted

Guest favourite

Cottage in Goshen

4.98 out of 5 average rating, 103 reviews

Country Cottage in Goshen

3–10 Feb

£134 per night

Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 254 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

14–21 Oct

£99 per night

Guest favourite

Flat in Winsted

4.94 out of 5 average rating, 35 reviews

Getaway for a weekend! Close to Ski Sundown.

19–26 May

£104 per night

Guest favourite

Guest suite in Winchester

4.94 out of 5 average rating, 54 reviews

Private Suite 2 Bedroom Deck Lake Views

1–8 Sept

£111 per night

Guest favourite

Guest house in New Hartford

4.87 out of 5 average rating, 83 reviews

Litchfields West Hill New Hartford Four Season BNB

20–27 Jan

£95 per night

Superhost

Flat in Winsted

4.87 out of 5 average rating, 30 reviews

1st Floor The Inn at Highland Lake

13–20 May

£151 per night

Superhost

Cottage in Winsted

4.88 out of 5 average rating, 16 reviews

Cottage Ease.

2–9 Aug

£223 per night

Guest favourite

Home in New Hartford

4.96 out of 5 average rating, 28 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

13–20 Sept

£201 per night

Show all

Quick stats about holiday rentals in Winsted

Total rentals	10 properties
Popular amenities	Kitchen, Wifi and Pool
Wifi availability	10 properties include access to wifi
Rentals with dedicated workspaces	10 properties have a dedicated workspace
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	720 reviews

Holiday rentals in Winsted

Top-rated holiday rentals in Winsted

Home in Colebrook

Chalet in Otis

Holiday home in Torrington

Guest suite in Canaan

Flat in Torrington

Home in New Hartford

Guest suite in East Granby

Cabin in Colebrook

Guest house in Granby

Guest suite in Morris

Cottage in Granby

Flat in Winchester

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Winsted holiday rentals

Stay near Winsted's top sights

Other great holiday rentals in Winsted

Cottage in Goshen

Flat in Copake Falls

Flat in Winsted

Guest suite in Winchester

Guest house in New Hartford

Flat in Winsted

Cottage in Winsted

Home in New Hartford

Quick stats about holiday rentals in Winsted

Total rentals

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Destinations to explore