Holiday rentals in Winsted

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Top-rated holiday rentals in Winsted

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Colebrook
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.
15–22 Feb
₹16,434 per night
4.99 out of 5 average rating, 199 reviews
Guest favourite
Holiday home in Torrington
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.
15–22 Jun
₹12,670 per night
4.97 out of 5 average rating, 128 reviews
Guest favourite
Guest suite in Canaan
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!!!
13–20 Aug
₹10,606 per night
4.98 out of 5 average rating, 289 reviews

Popular amenities for Winsted holiday rentals

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
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1–8 Nov
₹11,939 per night
5.0 out of 5 average rating, 318 reviews
Guest favourite
Flat in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
29 Aug – 5 Sep
₹7,663 per night
4.93 out of 5 average rating, 247 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
15–22 Nov
₹29,148 per night
4.94 out of 5 average rating, 345 reviews
Guest favourite
Farm stay in Ancram
Relaxing secluded stay with loving social animals.
7–14 Oct
₹11,584 per night
4.95 out of 5 average rating, 257 reviews
Superhost
Flat in Winsted
Haven at Highland lake
25 Nov – 2 Dec
₹5,779 per night
4.86 out of 5 average rating, 59 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
16–23 Jul
₹7,973 per night
4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Winsted
1st Floor The Inn at Highland Lake
16–23 May
₹10,944 per night
4.86 out of 5 average rating, 28 reviews
Guest favourite
Guest house in New Hartford
Litchfields West Hill New Hartford Four Season BNB
15–22 Jul
₹10,073 per night
4.88 out of 5 average rating, 75 reviews
Superhost
Guest suite in Torrington
Private Suite with its own entrance & bathroom
26 Dec – 2 Jan
₹6,826 per night
4.79 out of 5 average rating, 117 reviews
Guest favourite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a great lake!
31 Jul – 7 Aug
₹17,322 per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
6–13 Nov
₹29,314 per night
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County
7–14 Feb
₹11,193 per night
4.93 out of 5 average rating, 55 reviews

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

670 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Litchfield County
  5. Winsted