Vacation rentals in Ossining

Apartment in Greenwood Lake

A front porch is framed by white railings, featuring three white Adirondack chairs positioned for relaxation. Lush greenery surrounds the area, creating a peaceful outdoor space. Steps lead down to a stone pathway, with trees visible in the background.

4.94 out of 5 average rating, 86 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

5 out of 5 average rating, 121 reviews

Home in Greenwood Lake

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

4.96 out of 5 average rating, 56 reviews

Condo in Vernon

New Luxury Ski Condo-2 Full Bathrooms

This newly renovated Great Gorge Village condo, the perfect getaway to be active or just relax with the whole family. There is so much to explore during every season. It's heaven for golfers, leaf peepers, skiers, snowboarders, hikers, bikers and water park explorers. For those looking to relax and unwind it's a great area to explore wineries, breweries and top- notch restaurants. Please note: the unit is located on the second floor. Also, the master bedroom loft suite is up a spiral staircase

4.96 out of 5 average rating, 26 reviews

Three individuals are standing on a wooden dock, overlooking a serene lake at dusk. Bright green kayaks are positioned beside them, with lily pads visible in the water. Soft evening light reflects off the lake's surface, creating a tranquil atmosphere.

Cottage in Glen Spey

Lakeside Cabin

Enjoy this popular destination that has guests returning year after year! Situated on a private road that leads to the most desired lake in the area. While the house itself is not on the lake, the lakefront footage to enjoy water-sports comes with the rental.Access to row boats, kayaks, canoes, fire pit, hammocks,bbq, swimming platform, swing set, Adirondack chairs,lakefront seating and more! The house is landscaped, and the lake is a quick 2-3 minute walk down a beautifully landscaped road!

4.89 out of 5 average rating, 141 reviews

Chalet in Goshen

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

4.85 out of 5 average rating, 133 reviews

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Cottage in Greenwood Lake

4.98 out of 5 average rating, 338 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

4.95 out of 5 average rating, 355 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

A stone patio area features wooden seating and tables, surrounded by vibrant autumn foliage. Colorful trees frame the scene, with glimpses of a pool area in the background under a clear blue sky.

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

4.99 out of 5 average rating, 174 reviews

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

4.92 out of 5 average rating, 140 reviews

A serene lake view is presented, showcasing calm waters bordered by lush greenery and residential homes on the opposite shore. A private dock is visible in the foreground, accompanied by a shaded gazebo. The bright blue sky reflects on the lake's surface.

Home in Hopatcong

Lakefront Hopatcong w/dock kayaks fishing near NYC

3800 sqt 4b 2.5b, stunning lakefront house on the largest lake in NJ. Breathtaking lake views from every room. Sunrise coffee at bedroom balcony. Grill in the sunset at the spacious patio, fishing off the private dock. two spacious living rm for multi family, well equipped kitchen, large washer dryer, 3 kayak, fishing rods, grill, everything you need for your group to have a comfortable lake retreat and make some beautiful memories. 1 hr to NYC.

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Popular amenities for Ossining vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Ossining's top sights

The Boathouse23 locals recommend

Rockland Lake State Park20 locals recommend

3 Westerly Bar and Grill15 locals recommend

The Great Jack O’Lantern Blaze14 locals recommend

First Village Coffee14 locals recommend

Baked by Susan9 locals recommend

Other great vacation rentals in Ossining

Apartment in Downtown Stamford

A stylish lobby area features large glass walls allowing natural light to flood the space. Lush greenery is displayed in various decorative pots, enhancing the vibrant atmosphere. Comfortable seating is arranged on a patterned rug, providing a welcoming environment for guests.

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

5 out of 5 average rating, 14 reviews

A serene backyard setting is surrounded by tall trees, showcasing a mix of open grassy space and partial woodland. Five white adirondack chairs are arranged around a firepit, with a dining table visible nearby, inviting outdoor gatherings.

Home in South Fallsburg

Renovated & Spacious 3BR Catskills Retreat

4.94 out of 5 average rating, 32 reviews

A serene bedroom features a spacious bed adorned with a colorful blanket. A warm-toned lamp stands beside a wooden nightstand. Natural light floods the room through large windows and a skylight, illuminating a stone fireplace and providing a view of the outdoors.

Home in New Milford

Serene Country home 24 mi Mohawk ski area

The entrance of Minerals Resort and Spa is showcased, featuring a prominent sign surrounded by vibrant autumn foliage and colorful flower beds. The building's stone accents and unique architecture complement the natural scenery of the lush mountains in the background.

4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

4.82 out of 5 average rating, 96 reviews

Home in Cornwall

State Forest Getaway

Cottage in Greenwood Lake

A wooden home is surrounded by lush greenery and manicured gardens. Flower beds with colorful blooms are visible in the foreground, while the house features a large deck. Mature trees provide a natural backdrop, enhancing the serene outdoor atmosphere.

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

A designated outdoor seating area features four wooden Adirondack chairs arranged around a stone fire pit. Lush green trees and shrubs create a natural backdrop, while a paver stone pathway invites relaxation and conversation in a serene setting.

4.92 out of 5 average rating, 119 reviews

Perfect Retreat! Ski in/out, hot tub, bike races.

A modern living area is highlighted by a large flat-screen TV above a tiled fireplace. Soft seating choices include a beige sofa with decorative pillows and two gray armchairs. Natural light enters through multiple windows, creating an inviting atmosphere.