Vacation rentals with a kayak in Monterey

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Top-rated kayak rentals in Monterey

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Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 171 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favorite

Home in Becket

4.93 out of 5 average rating, 138 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Guest favorite

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lake Retreat-kayaks/SUP/central air

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the bays, coves and creeks -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 160 reviews

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.

Guest favorite

Home in Monterey

4.89 out of 5 average rating, 102 reviews

Hilltop Retreat w Magic View! Ski Butternut 15min

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.

Guest favorite

Home in Catskill

4.94 out of 5 average rating, 172 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access year round. We provide kayaks & stand up paddle board. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Fish right off the lawn. Enjoy brunch or dinner in the Gazebo suspended over the Hudson with a private chef (inquire about availability). Explore Hudson, Saugerties, Woodstock....honestly, you'll not want to leave.

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 268 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Guest favorite

Home in Averill Park

4.98 out of 5 average rating, 170 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

Guest favorite

Home in Otis

4.97 out of 5 average rating, 104 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Guest favorite

Home in Copake

4.96 out of 5 average rating, 191 reviews

Lakefront +views +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.

Guest favorite

Cottage in Lanesborough

4.84 out of 5 average rating, 274 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016), private cottage 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. For conditions message Jill.

Superhost

Home in Craryville

4.84 out of 5 average rating, 137 reviews

Copake Lake Cottage by Hiking, Skiing, Waterfalls

Renovated, art-filled cottage just 500 ft from Copake Lake. This 2 bedroom 1 bathroom house is close to hiking trails, waterfalls, apple picking, & a winery in the fall, and in winter, there’s skiing at Catamount, and a distillery nearby. A house for all seasons! Please note the lake is across a quiet road from house, and the dock is in the lake from mid-May to mid-September.