Vacation rentals in Woodridge Lake

Halo Hollow Haus - Litchfield Lake & Ski Haven

Rest, relax, and recharge in this serene and stylish space. Halo Hollow Haus is a lake house and ski lodge offering boutique vacation vibes and year-round country beauty. Nestled in the beautiful Woodridge Lake community, you'll enjoy lake life at its finest while just minutes away from all that Litchfield County has to offer. Enjoy classic New England towns, swimming, skiing, hiking, fishing, parks, golf, mountains, foliage, antiquing, vineyards, excellent restaurants, and cultural attractions.

Location · Family · View

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!

Family · Location · Layout

Contemporary Rustic Lake Chalet

Chalet surrounded by glass and natural sunlight with cathedral ceilings. Fully stocked and equipped kitchen with island bar and chairs . Dining table seating for 6. Sony large screen TV. Bose surround sound Beautiful fireplace..HVAC over fireplace. Window AC's in bedrooms. Outdoor dining seats 6. Large screened in porch with a beautiful large patio, hot tub, gas grill. Charcoal weber grill & fire pit. Lake with 4 private beaches . 14night stay for pool use. 2 hours from NYC.

Family · Location · Hiking

Peaceful Lakefront Oasis in Litchfield County

Our lovingly cared for lakefront home invites you for rest and relaxation. Jump off the dock for a swim or take a paddle board or kayak ride. Enjoy a scenic meal on the deck, equipped with a gas grill. Indoor fun includes ping pong, an entertainment center and board games. And a basketball hoop sits in the driveway. All at only 100 miles from NYC! *Note that stays >2 weeks include access to our HOA amenities (tennis courts, beaches, and pool), and the dock is available mid-May to mid-Oct.

Family · Location · Quiet

Litchfield Hills Lakefront Getaway!

YellowBird welcomes guests with luxury vaca vibes + gorgeous water and sunset views on friendly Woodridge Lake, just minutes from Litchfield County’s charming small towns, golf, hikes + ski resorts. -2 hrs NYC, 2.5 hrs Boston, only 10 min from Litchfield village center -Gorgeous & fun all year -Enjoy 150 ft of lakefront, swimming, fishing, parks, golf, hiking, mountain and countryside vistas, foliage, covered bridges, antiquing, vineyards, top restaurants, cultural activities & skiing

Location · Family · Sleep quality

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

Value · Location · Hospitality

Sun-Soaked Chalet Near Lake and Ski Mountain

Relax with the whole family on a country getaway in a bucolic lake community! Soaring ceilings and high windows flood the great room with natural light, and the huge fireplace makes for wonderful cozy family game nights. Relax on the hammock in the shade, or play bocce or corn hole in the backyard. Fire up the Weber grill on the back porch, and roast marshmallows over the fire pit on summer nights. Guests staying 14 days or longer can access the swimming pool, lake, and tennis courts.

Location · Value · Nearby

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.

Value · Family · Bathroom

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

Family · Location · Amenities

Pristine Downtown 2BR Cozy Fireplace & Parking

Stay in a professionally cleaned, cozy, 1st floor, 2BR apartment designed for comfortable short stays, weekend visits, work trips, and longer stays alike. Located just minutes from downtown Torrington, you’ll be within minutes of restaurants, coffee shops, the Warner Theatre, Nutmeg Ballet, and local events while still enjoying a relaxing place to unwind after a busy day. Our goal is simple: A spotless, comfortable, and stress-free stay that feels easy from check-in to checkout.

Value · Family · Walkability

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Family · Value · Checkout

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

Value · Location · Backyard