Family-friendly holiday rentals in Sherman

Cozy Scenic New England rural retreat hike & kayak

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian Trail & other great hiking. Family friendly beach on Lake nearby. Pets welcome. Inquire min stay requirements.

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!

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Idyllic retreat on the water <1.5 hrs to NYC.

Private getaway on 3+ acres on the river with no visible neighbors, sit by the river or in the enclosed patio with view of the water, walk the trails in the area. Great for short escapes or longer discounted stays enjoy great restaurants, antiquing, swimming, hiking, and access to all New England has to offer. In spring, summer and fall lots of open air activities to be had. Fishing, boating, farmers markets and flea markets. In winter many nice walks to be had, skiing is not too far away.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

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 Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

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 inflatable two person kayaks are available for use from May 1 to November 1..

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.