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

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

€ 263 per night
Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

13–20 Sep

€ 122 per night
Guest favourite

Holiday home in Torrington

4.97 out of 5 average rating, 128 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.

1–8 Mar

€ 180 per night

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

Farm stay in Ancram

4.95 out of 5 average rating, 257 reviews

Relaxing secluded stay with loving social animals.

13–20 Jan

€ 145 per night
Guest favourite

Flat in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

22–29 Nov

€ 181 per night
Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

13–20 Jun

€ 385 per night
Superhost

Flat in Winsted

4.85 out of 5 average rating, 60 reviews

Haven at Highland lake

5–12 Feb

€ 65 per night
Guest favourite

Flat in Winsted

4.94 out of 5 average rating, 34 reviews

Getaway for a weekend! Close to Ski Sundown.

14–21 Sep

€ 122 per night
Guest favourite

Guest house in New Hartford

4.86 out of 5 average rating, 79 reviews

Litchfields West Hill New Hartford Four Season BNB

28 Nov – 5 Dec

€ 109 per night
Guest favourite

Guest suite in Winchester

4.94 out of 5 average rating, 51 reviews

Private Suite 2 Bedroom Deck Lake Views

16–23 May

€ 127 per night
Guest favourite

Flat in Winsted

4.87 out of 5 average rating, 30 reviews

1st Floor The Inn at Highland Lake

17–24 Mar

€ 225 per night
Guest favourite

Home in Winsted

5.0 out of 5 average rating, 28 reviews

Lake House- Great for Families

30 Apr – 7 May

€ 424 per night
Guest favourite

Home in New Hartford

4.96 out of 5 average rating, 27 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

13–20 Aug

€ 259 per night
Guest favourite

Home in Torrington

4.99 out of 5 average rating, 85 reviews

Country living at it's finest

6–13 Apr

€ 147 per night
Superhost

Home in Torrington

4.93 out of 5 average rating, 56 reviews

Charming Home in Litchfield County

9–16 Oct

€ 175 per night

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