Holiday rentals with a kayak in Putnam County

Lakefront Brewster Vacation Rental w/ Private Dock

If you’re seeking lake life with all the comforts of home, book this 3-bedroom, 2-bathroom Brewster vacation rental! This spacious cottage features a cozy living area with a Smart TV, a full kitchen, and on-site access to Lake Tonetta. Sip your morning coffee on the patio, then launch your boat from the dock, coast along the shore, and cast a fishing line. Hoping to explore? Go biking at Empire State Trailway or hike the Putnam Trailway! When night falls, gather around the dock for stargazing.

Pet Frndly Lake House w/Fireplace & Fire Pit W/D

Relax with the whole family at this peaceful place to stay. You’ll enjoy a yard, parking for 2 cars, fire pit, BBQ grill and a peaceful neighborhood where you can enjoy day walks. Your pets are welcome during your stay- we will ask about the breed and size- pets are not allowed on the beds or couch. You also have access to the lake just steps from this home. Train station is just 10 min away. Enjoy the farms, restaurants and scenery of North Salem, a place where your whole family can enjoy!

Peaceful lake and woodland retreat

Welcome to beautiful Lake Peekskill. This self-contained guest suite is situated in the entire lower level of a private house down several steps, featuring its own private door access, as well as parking on site. Guests can access the grounds of the house including areas to sit, a native wildflower pasture, and a woodland with wildlife including deer, foxes, and birds. Lake access is a 15-min walk away (or a 3-min drive) to a beach area where guests can swim, fish, and make use of two kayaks.

MountainView Retreat: Scenic View, Sauna, Hiking

MountainView sits perched on top of a mountain with uninterrupted views of the landscape beyond. The houses updates provide a modern feel while still being cozy in all four seasons and prioritizes bringing the outdoors in. Located in the scenic Hudson Valley and just 75 minutes by train or car to NYC. From the house you can expect to enjoy... - Year round sunsets - Great hiking nearby - Relax with an infrared sauna - Cozy up to a fireplace - Family meals in the fully equipped kitchen

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Cozy Modern Lake Access Retreat • Hudson Valley

Step into serenity at The Dugout, a beautifully renovated mid-century retreat among the pines in Garrison, NY — just over an hour from NYC and a quick drive to the Metro North. Thoughtfully restored this 1960s gem blends timeless character with high-end comfort for the perfect countryside escape. Whether you're kayaking on Cortlandt Lake, sipping wine on the screened-in deck, or curling up by the wood-burning fireplace, The Dugout is your peaceful getaway in the heart of the Hudson Valley.

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Historic family house in downtown Beacon

As seen on HGTV's small town potential, our house is a large, spacious family home with private waterside access located steps away from Main St in Beacon. This 1860s house has many original features but modernised with a lot of color and character. It's our family home that we rent when we're out of town. It has 3 bedrooms that sleep 5 and other rooms with sofa beds for bigger groups up to 9 people. There are bikes, kayaks, a BBQ and many games to enjoy during your stay.

Lakefront Hudson Valley Cottage w/Hot Tub/Fire Pit

Relax at a cozy lakefront cottage in the Hudson Valley, just about an hour from New York City. Perched on a hill with beautiful lake views, this 1940s retreat is perfect for a weekend getaway. Enjoy swimming, kayaking, and fishing right from the backyard, then unwind in the hot tub or gather around the fire pit. Inside, warm up by the wood-pellet stove and enjoy peaceful nature views—ideal for couples, friends, or a quiet escape.

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Private Beach on Lake Oscawana by Mosaic Getaways

Rustic lake house w/ private dock, beach, kayaks, canoe Gorgeous living room with stone fireplaces, 70inch TV & tons of seating Multiple decks & outdoor seating areas spread amongst the nature rich surroundings Multiple desks & WiFi, great for remote work Professionally managed by Mosaic Getaways