
Places to stay near Ski Sundown
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Top-rated holiday rentals near Ski Sundown
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Rustic Pond Cabin: Nature, Stars & Serenity
Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

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.

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

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

The Carriage House Wine Vineyards nearby
Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

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.

Twin Lakes Designer A-frame Stone Cottage
*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

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!

Private Woodland Sanctuary—3 mins to a lake beach!
Kick back and relax in this calm, stylish space with your loved ones and furbabies in New Hartford, CT. Indulge in the privacy and serenity of this 4 acre wooded home only 3 mins away from CT's most pristine lake, West Hill Lake. The lake is super approachable and the beach is kid friendly! Enjoy the sunshine and morning coffee in our unique solarium.

Beautiful Brook-side Log Cabin on 3 Private Acres
Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.
Popular amenities for holiday rentals near Ski Sundown
Condo rentals with Wi-Fi

Meadow View

Spacious Condo • Quick Drive to Everything

Spacious 3 bedroom apt in Lenox historic downtown

New Britain "Joy of Small Space" Condo

Entire place to yourself Cromwell/Middletown Line

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Peaceful 1BR Condo with Pond View

Newly Renovated Clean Comfortable Relaxing Ideal
Family-friendly house rentals

The Farmhouse

The Getaway-HOST & Co.

Luxe Bolton Lake

Romantic Getaway at The Lake!

The Waterfall House

Chic Hudson Farmhouse w/ Fireplace & Porch

Tucked-away Charming Forest Cabin w/ Private Brook

Charming Home in Litchfield County on a MAIN ROAD!
Apartment rentals with air conditioning

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

Garden View Apartment on Main St. Walk to Downtown

The Village Apt

Charming apartment with breathtaking view!

Getaway for a weekend! Close to Ski Sundown.

HideAway UConn Coventry RockFarm BnB Breakfast A+

Spacious Cozy Guest Suite

Western Mass Retreat!
Other great holiday rentals near Ski Sundown

Berkshires Cottage by Lake. Year Round Adventures.

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Blackberry Cottage

The Little Red Schoolhouse ~ Circa 1877

Guest Suite at Wisteria Gardens

Berkshire Treehouse Retreat

The Red Cabin-Secluded Getaway with backyard Brook

Treehouse - Countryside - Farm Animals - Fire Pit
Destinations to explore
- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Hammonasset Beach State Park
- Bousquet Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- University of Connecticut
- Millbrook Vineyards & Winery
- Mount Southington Ski Area
- Naumkeag
- Hudson Chatham Winery
- Norman Rockwell Museum
- Brownstone Adventure Sports Park
- Hancock Shaker Village
- Smith College





