
Kent Falls State Park, Kent
10/10 – 10/12
$488/nighttotal: $976 (2 )
The Ultimate Weekend Escape From Nyc For Families
1 3apartment , Kent
This renovated 4-bedroom, 2-bathroom condo in Kent is located approximately 120 miles from New York City.
This spacious apartment offers a private primary suite with a fireplace and office, a guest bedroom with a private deck, a kid-friendly game room with Ms. Pacman, sleeper chairs, and a massive deck with a fire pit and grill, all accessible via a heated garage with additional game facilities.
This spacious apartment offers a private primary suite with a fireplace and office, a guest bedroom with a private deck, a kid-friendly game room with Ms. Pacman, sleeper chairs, and a massive deck with a fire pit and grill, all accessible via a heated garage with additional game facilities.

Kent Falls State Park, Kent
10/10 – 10/12
$489/nighttotal: $978 (2 )
The Red Country Cottage
4 3apartment , Amenia
This 4-bedroom, 2-bathroom cottage in Amenia offers a secluded creekside setting within walking distance to the town center, providing direct access to the 26-mile Harlem Valley Rail Trail and proximity to wedding venues, Lime Rock Racing, and skiing destinations.
This family-friendly 1100 square foot rental accommodates up to 8 guests with a full kitchen, air conditioning, a terrace, garden, and provided bicycles, making it ideal for exploring nearby Millbrook Vineyards, Mohawk Mountain Ski Area, and Macedonia Brook State Park.
This family-friendly 1100 square foot rental accommodates up to 8 guests with a full kitchen, air conditioning, a terrace, garden, and provided bicycles, making it ideal for exploring nearby Millbrook Vineyards, Mohawk Mountain Ski Area, and Macedonia Brook State Park.

Kent Falls State Park, Kent
10/04 – 10/16
$511/nighttotal: $6132 (12 )
Spa Cabin With Sauna, Hot Tub And Cold Plunge
1 2cabin , Cornwall
The Little Bell Cabin, a two-bedroom cottage, is situated in the Berkshire Mountains foothills, offering easy access to attractions like Covered Bridge Electric Bikes and Hopkins Winery.
This Cornwall getaway boasts a jacuzzi, a wood-fired stone fire pit, and a Weber BBQ grill, accommodating up to four guests with amenities including a fully equipped kitchen and two queen-sized bedrooms.
This Cornwall getaway boasts a jacuzzi, a wood-fired stone fire pit, and a Weber BBQ grill, accommodating up to four guests with amenities including a fully equipped kitchen and two queen-sized bedrooms.

Kent Falls State Park, Kent
10/04 – 10/16
$331/nighttotal: $3972 (12 )
Magical Woodland Getaway
1 2apartment , Warren
This Litchfield Hills post-and-beam home in Northwest Connecticut offers a secluded 2-acre setting near Warren, Connecticut, a 10-minute drive from Lake Waramug State Park, 6 minutes from Kent Falls State Park, and 18 minutes from Mohawk Mountain Ski Area.
The three-bedroom, two-bathroom house sleeps six and features a chef's kitchen with Cafe appliances, a deck with views of a pond, an outdoor fire pit, and high-end furnishings from Arhaus, Pottery Barn, and West Elm; nearby wineries and distilleries include Hopkins and Springhill Vineyards, Litchfield Distillery, and Tenmile Distillery.
The three-bedroom, two-bathroom house sleeps six and features a chef's kitchen with Cafe appliances, a deck with views of a pond, an outdoor fire pit, and high-end furnishings from Arhaus, Pottery Barn, and West Elm; nearby wineries and distilleries include Hopkins and Springhill Vineyards, Litchfield Distillery, and Tenmile Distillery.

Kent Falls State Park, Kent
10/10 – 10/12
$562/nighttotal: $1124 (2 )
Quiet Country Farmhouse Getaway Close To Skiing
5 3apartment , Cornwall
This five-bedroom farmhouse, located on a private 45-acre property in Cornwall, is a secluded rural retreat just a five-minute drive from the Mohawk Mountain Ski Area. The farmhouse, which sleeps up to 10 guests, features two fireplaces, a cast-iron stove, and a kitchen with a fridge, along with a private parking area.

Kent Falls State Park, Kent
10/11 – 10/13
$428/nighttotal: $856 (2 )
Cozy Hillside Retreat Close To Kent
1 1apartment , Kent
The Nest guesthouse is located in the Litchfield Hills, just minutes from the restaurants, shops, and galleries of downtown Kent. The surrounding area offers a peaceful retreat with stunning views of a nature preserve.
The guesthouse is a modern, two-bedroom home that can accommodate up to four guests. It features a private outdoor deck, a shared pool, and a fully equipped kitchen.
The guesthouse is a modern, two-bedroom home that can accommodate up to four guests. It features a private outdoor deck, a shared pool, and a fully equipped kitchen.

Kent Falls State Park, Kent
10/10 – 10/12
$258/nighttotal: $516 (2 )
Mountain Creek Getaway
1 3house , Dover Plains
This Dover Plains farmhouse apartment, near the New York/Connecticut border, offers convenient access to the Appalachian Trail, Bulls Bridge hiking trails, and Thunder Ridge Ski Area, though precise distances are not specified.
The 2-bedroom, 1-bathroom rental accommodates up to 5 guests and features a queen bed, sleeper sofa, twin bunk bed, full kitchen with dishwasher, air conditioning, a relaxing deck with electric fireplace, and a private setting with parking.
The 2-bedroom, 1-bathroom rental accommodates up to 5 guests and features a queen bed, sleeper sofa, twin bunk bed, full kitchen with dishwasher, air conditioning, a relaxing deck with electric fireplace, and a private setting with parking.

Kent Falls State Park, Kent
10/04 – 10/16
$550/nighttotal: $6600 (12 )
The House On High Meadow Farm
1 2apartment , Sharon
This farmhouse is located in the scenic Housatonic River Valley, a short drive from Sharon, Connecticut, and close to the towns of Amenia and Wassaic in New York. The four-bedroom, two-bathroom farmhouse sleeps eight guests and features a swimming pool, air conditioning, and a peaceful country setting with stunning mountaintop views overlooking the Housatonic River Valley.

Kent Falls State Park, Kent
10/10 – 10/12
$627/nighttotal: $1254 (2 )
Sugarloaf Mountain Farm
1 3apartment , Kent
Sugarloaf Mountain Farm is located in the quiet hills of Litchfield County, Connecticut, just a short drive from the charming town of Kent. The farmhouse has consistently received excellent ratings for its cleanliness, location, and overall experience.
The entire house is available for guests, accommodating up to eight people comfortably. The farmhouse features a fully equipped kitchen, a screened porch, a large backyard with a fire pit, and a playset for children.
The entire house is available for guests, accommodating up to eight people comfortably. The farmhouse features a fully equipped kitchen, a screened porch, a large backyard with a fire pit, and a playset for children.

Kent Falls State Park, Kent
10/04 – 10/16
$518/nighttotal: $6216 (12 )
Modern Woodland Retreat In Kent, Ct
1 2apartment , Kent
This newly renovated post-and-beam home sits on 25 acres of woodland near Kent, Connecticut, minutes from town amenities and a 20-minute drive from Mohawk Mountain Ski Area.
This three-bedroom, two-bathroom house offers a spacious open floor plan including a kitchen, dining area, living room, and yoga room, accommodating up to six guests and featuring three fireplaces, a screened-in porch, and access to nearby hiking trails; an outdoor patio with a BBQ and fire pit will be ready Spring 2025.
This three-bedroom, two-bathroom house offers a spacious open floor plan including a kitchen, dining area, living room, and yoga room, accommodating up to six guests and featuring three fireplaces, a screened-in porch, and access to nearby hiking trails; an outdoor patio with a BBQ and fire pit will be ready Spring 2025.

Kent Falls State Park, Kent
10/10 – 10/12
$231/nighttotal: $462 (2 )
Cozy Country Cabin
1 3apartment , Cornwall
This 1-bedroom, 1-bathroom apartment in Cornwall offers internet, a kitchen, and parking for up to 2 guests, located in the Housatonic River Valley a short drive from Kent Falls and 15 miles from the 10 Mile train station. Enjoy outdoor activities like hiking and fishing, relax in the jacuzzi tub or with the massage chair, and utilize the deck with BBQ facilities, with fine dining options nearby.

Kent Falls State Park, Kent
10/10 – 10/12
$505/nighttotal: $1010 (2 )
Dainty New Preston Cottage W/ Dock & Lake Views!
1 3cottage , Washington
This New Preston, Connecticut cottage offers easy access to Lake Waramaug and Mount Bushnell State Park, located within three miles of Hopkins Vineyard and Lake Waramaug State Park.
The pet-friendly home features two bathrooms, a fully equipped kitchen with microwave and dishwasher, air conditioning, and free Wi-Fi in public areas; guests can enjoy nearby hiking, wine tasting, and other Litchfield Hills attractions.
The pet-friendly home features two bathrooms, a fully equipped kitchen with microwave and dishwasher, air conditioning, and free Wi-Fi in public areas; guests can enjoy nearby hiking, wine tasting, and other Litchfield Hills attractions.












