Vacation rentals with a kayak in Otis

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Hilltop Retreat w Magic View! Lake Beach 1 mile

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

Hot Tub w/ Foliage Lake Views, Fire Pit & Kayaks

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

Modern Mid-Century Cottage - Hike, Swim & Shop!

Let all your worries fade away in this beautifully remodeled modern cottage! Our 3 bedroom, 2 bath can sleep 8 adults in 2 Queen Beds, 2 Twin Beds and a Queen Sleeper Sofa. Relax by the fire pit out back or take out our 2 two person Kayaks and enjoy the lake in the summer, visit Catamount Ski Resort or other nearby ski mountains in the winter. The large, custom dinner table seats 8 comfortably with lots of room to hang, play games, watch movies and more. Guests must be 25 years old to rent.

Lake front retreat - Stylish Berkshire home

Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

Wildlife Retreat in the Forest

Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.

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 n and surrounded by nature! Private Great WIFI! Close to quaint ski resorts n dispensaries

Onomea Farm

Relax and watch the sheep graze in the pasture. Enjoy the amazing night sky. Fabulous modern two bedroom handicapped accessible in law suite with separate entrance. Fireplace, washer/dryer, heat, central A/C. Queen bed on main level, King and pull out sofa on 2nd floor. Both bedrooms have 50” TV’s. Full kitchen. Located in North Granby, CT. Quiet location yet close to major attractions and Bradley airport. We have 8 resident well behaved dogs THAT RUN FREE on the property -

Kayak, pet a Highland cow, have dinner in Hudson!

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount. Cozy wood burning stove as well as outdoor fire pit. Ask about a farm visit!

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!