Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite

Home in Greenwood Lake

5 out of 5 average rating, 121 reviews

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!

Superhost

The living area features large windows that allow natural light to fill the space, with views of the surrounding greenery. A comfortable sectional sofa is positioned around a wooden coffee table, creating a cozy gathering spot. A wall-mounted television is visible above a rustic wood-paneled fireplace.

Home in Lehman township

4.86 out of 5 average rating, 166 reviews

Cozy Family Poconos Home: Game Room, Pools,Firepit

@goldenpoconos Are you tired of searching for houses for your perfect vacation? You can stop right now because this is it! Welcome to our family owned Golden Retreat in the SawCreek Community! Enjoy a cup of fresh coffee while the living room is set ablaze with golden sunlight. Guests will have access to 3 bedrooms/2 bathrooms, large fully stocked kitchen, jacuzzi, loft with board games and entertainment, and a game room in the basement filled with billiards, ping pong, air hockey, and more!

Top guest favorite

A serene outdoor area features several gray chairs arranged around a fire pit. The grassy lawn leads to a tranquil lake, reflecting the vibrant colors of surrounding trees. A dock is visible in the distance, enhancing the natural beauty of the setting.

Cottage in Beach Lake

4.99 out of 5 average rating, 117 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

This gem of a vacation rental is perfectly situated on a private lake. Recently renovated, the main level features an open concept living area, with a cozy fireplace for chilly evenings, upgraded kitchen, a master bedroom with a luxurious en-suite bathroom. A charming loft serves as a cozy relaxation spot or additional sleeping area. Each room offers a spectacular lake view. Two full bathrooms ensures everyone has space to unwind. Outdoor includes a hot tub, perfect for relaxation by the lake.

Top guest favorite

Home in Glen Spey

4.99 out of 5 average rating, 135 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakefront retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,Shrewd Fox Brewery Spring 2025!

Guest favorite

The living area features a comfortable purple sofa and armchair, arranged around a light coffee table. A flat-screen TV is mounted above a fireplace, providing a cozy focal point. Natural light filters through the windows, enhancing the inviting atmosphere of the shared space.

Townhouse in East Stroudsburg

4.89 out of 5 average rating, 179 reviews

Mountain Air - Jacuzzi, Hiking, Biking & River

Our house is just up the road from the Shawnee Mountain Ski Area. Located between Bushkill Falls and the Delaware National Recreation Area, it offers Skiing, hiking, biking, rivers, streams, and waterfalls. From Spring to Fall, easy access to kayak or canoe rentals. Numerous golf courses just minutes away. The historical town of Delaware Water Gap and Stroudsburg offers a variety of restaurants, music venues, wineries, breweries and boutiques. Best of all, we are only 75 minutes west of NYC.

Guest favorite

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

4.92 out of 5 average rating, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Top guest favorite

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

Located 2hrs from NYC, 7mins from Livingston Manor and close to Belleayre and Plattekill ski mountains. Sat atop a mountain, with 5 acres that sweep away from the property revealing stunning long distance views. Beautiful light throughout - front room with fireplace, full renovated kitchen, lounge, dining area, master bedroom, 1 large guest room, office / single bedroom, 2 bathrooms and huge covered back porch + a full home gym complete with Peloton bike, Peloton tread + ping pong table.

Top guest favorite

Home in Bushkill

4.97 out of 5 average rating, 135 reviews

Sweet Home Poconos

Beautiful home with plenty outdoor living area, access to pools, sport courts, lake, our own ski slopes and so much more! Within minutes of our gates there is horseback riding, zip lines, tree adventure programs, go-kart racing, Delaware River National Park, walking trails, Shawnee Ski Area. If you want to go for a drive you’ll get to Camelback, Kalahari Water Park, The Commons Outlet Mall which features over 100 designer stores. Most important, we welcome guests of all walks of life

Guest favorite

An inviting living area features a spacious sectional sofa positioned beside a wooden coffee table. Natural light floods through large windows, illuminating the rustic wood accents and modern appliances in the kitchen area. A staircase leads to the upper level.

Home in Greentown

4.96 out of 5 average rating, 264 reviews

Brand new one bedroom paradise

Gorgeous Brand new Cottage! Close to many ski resorts! Montage, Jack Frost, Elk Mountain Big Bear, and Camelback. 25-35 minutes out. Away from the hustle and bustle!Perfect getaway! All you need is your clothes and food! Fully sanitized& filled with all essentials. GLAZE under the stars around the fire pit. This beautiful house is minutes away from grocery stores, shops and other facilities. 25 minutes away from Woodloch Pines and 20 minutes from SkyTop!

Guest favorite

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

4.92 out of 5 average rating, 140 reviews

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.

Guest favorite

Home in East Stroudsburg

4.97 out of 5 average rating, 120 reviews

Stylish 4Bdr Mountain Retreat, Hot Tub, Pool

Welcome to Serenity Falls! A true gem mountain house with its own private waterfall! Large deck with a private hot tub, dining area, and magical atmosphere with entertainment for all. This retreat also offers a full-size billiards table and a game room with PS4, darts, and other toys for all ages. Enjoy delicious meals with loved ones on the spacious deck with a BBQ grill and take in the breathtaking Poconos scenery. What else can you ask for?

Superhost

A serene view of the property nestled among tall trees, showcasing a blend of natural greenery and a shoreline. Wooden stairs lead from the rocky beach up to the house, providing access to the lush surroundings.

Home in Hawley

4.9 out of 5 average rating, 124 reviews

Poconos Lakefront Best View Lake Wallenpaupack⛷

The best view on the lake I would describe it as hypnotic. Close to several ski resorts. Montage, Elk, Camelback, Jack Frost , and Big Bolder are all less than 40 min drive,!!!two fireplaces and a fire pit !!The pictures do not do it justice. Brand new everything look at the pictures. Huge deck private dock and swim dock!! Perfectly situated between silver birches and the boat house. Walk the dyke to the beach!!