
Places to stay near Ski Sundown
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Top-rated vacation rentals near Ski Sundown
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

The Carriage House Skiing 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.

Berkshire Treehouse Retreat
Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

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.

Pristine Cozy Walkable Downtown 2BR Getaway
Cozy, pristine 2BR retreat in downtown Torrington. Guest favorite professionally cleaned after every stay. Minutes from the historic Warner Theatre, restaurants, and shops. Full kitchen, fast WiFi, workspace, keyless entry, and free off-street parking. Relax by the electric fireplace after exploring the scenic Litchfield Hills. Perfect for couples or remote workers. This private first-floor apartment is part of a quiet two-unit home.

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 vacation rentals near Ski Sundown
Condo rentals with wifi

Meadow View

Spacious Condo • Quick Drive to Everything

New Britain "Joy of Small Space" Condo

Entire place to yourself Cromwell/Middletown Line

Luxury furnished condo. Attached garage. Fireplace

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Hartford Home w/ Skyline Views near Bushnell Park!

Comfortable Relaxing Ideal Oasis
Family-friendly house rentals

The Farmhouse

The Getaway-HOST & Co.

Luxe Bolton Lake

Idyllic family retreat - spacious lake home,

Tucked-away Charming Forest Cabin w/ Private Brook

Charming Home in Litchfield County on a MAIN ROAD!

Connecticut Chalet: Summer Retreat on 5 Acres

Jaw dropping mountain & lake views
Apartment rentals with air conditioning

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

Your home away from home for Comfort & Convenience

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

Enjoy every season the Berkshires have to offer.
Other great vacation rentals near Ski Sundown

Artist Cottage

Stylish Shales Brook Cottage-Cozy up to happiness

Woolly Acres Farm

Private Suite 2 Bedroom Deck Lake Views

Romantic Getaway at The Lake!

Creekside Cabin with Wood Fired Hot Tub & Firepit

The Cottage on Babbling Brook

Rustic Pond Cabin: Nature, Stars & Serenity
Destinations to explore
- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Hammonasset Beach State Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Mount Southington Ski Area
- University of Connecticut
- Naumkeag
- Norman Rockwell Museum
- Millbrook Vineyards & Winery
- Berkshire Botanical Garden
- Hancock Shaker Village
- Devil's Hopyard State Park
- Hudson Chatham Winery





