Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

Home in Coolbaugh Township

4.64 out of 5 average rating, 69 reviews

LAKEFRONT HOUSE SLEEP 11,WIFI, NETFLIX, BOAT

This LUXURIOUS newly renovated LAKE HOUSE is sure to impress with its stunning views and peaceful atmosphere!!Whether you are in the mood for active or relaxing getaway,you will sure find what you are looking for any time of the year. pools, beaches,playgrounds,basketball and tennis courts.minutes away from the Kalahari Resort and Waterpark, Mount Airy Casino Resort,The Crossings Premium Outlets,Claws 'n' Paws Wild Animal Park,Quiet Valley Historical Farm,numerous breweries,restaurants,and more!

Top guest favorite

Townhouse in Lake Harmony

4.85 out of 5 average rating, 20 reviews

Sleep Beauty, Poconos Vacation 2BR 4Beds Sleep 6+

Note: This property is very nice & very clean renovated Nov 2023. Escape to our newly renovated 4-bed townhome, just 1 min to Jackfrost Golf & Ski Resort, 25 m to Switzerland of America. Your family vacation, a wood-burning fireplace, all new interior/appliances. Sleep in luxury on king memory foam mattress. Enjoy the lake and golf course near Property, clean and private, a relaxing vacation with modern amenities. For an unforgettable Poconos adventure with your loved ones! Very friendly host.

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

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

4.96 out of 5 average rating, 26 reviews

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!

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 charming outdoor space features a rustic tiki bar with wooden accents, next to a well-maintained grassy area. Sun loungers are placed on the wooden deck, and a cozy seating arrangement under a canopy provides a shaded spot for relaxation.

Tiny home in Belmar

4.87 out of 5 average rating, 198 reviews

Best Couples Retreat Greatest Location of Belmar

A tastefully decorated detached back house studio apartment in a private fenced in yard only 2 blocks from the beach! Perfect for a couple or 2.. Enjoy the outdoors and the fresh ocean air by sitting in the nice furniture patio set, by the tiki bar or next to the firepit. Gather around tables inside or out with plenty of seating. Studio is set with great amenities starting with the huge 82 inch smart 4K TV with surround sound, WiFi, and Amazon Dot. Stocked kitchen w/ stainless appliances!

Guest favorite

A welcoming living area is highlighted by a stone fireplace, surrounded by wooden walls and a high ceiling. Large windows provide natural light and views of the outdoors. Comfortable seating arrangements are complemented by a glass coffee table and tasteful decor.

Home in Tobyhanna Township

5 out of 5 average rating, 17 reviews

Lakeview Home | Pet Friendly

Nestled in the serene Pocono Mountains, the beautifully renovated Honovi House, offers a tranquil retreat that blends natural beauty with modern comfort. This charming home is perfect for those seeking a peaceful getaway or a cozy year-round residence. Located in a quiet, wooded, and gated neighborhood, the property provides easy access to a variety of outdoor activities such as hiking, fishing, swimming, and skiing, making it an ideal location for nature enthusiasts and adventure seekers.

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

A swimming pool is complemented by a waterslide, from which water cascades into the pool. Lush greenery is visible in the background, providing a natural setting. Two diving boards are situated adjacent to the pool, enhancing recreational options.

Townhouse in Pocono Pines

4.89 out of 5 average rating, 121 reviews

Mountain Lake House

Now includes SIX FREE MEMBERSHIPS to our Pool, Lake and Tennis Clubs!!! Our clean, comfortable townhome has everything you need to enjoy this beautiful area year round. Summer visitors enjoy our sparkling heated community pool, beach, golf course, and lake. In winter, 3 major ski areas are nearby. The Poconos are renown for fall foliage, and we’re only minutes away from Kalahari, North America’s largest indoor water park. Minimum Age to Rent is 25. Township Registration #012434.

Top guest favorite

A spacious kitchen area features wooden paneling and modern appliances. A large island with four stools sits centrally, illuminated by pendant lights. Cooking essentials and a coffee station are neatly arranged, while a cozy living area is visible in the background.

Cabin in Tafton

5 out of 5 average rating, 77 reviews

Cozy Cabin! BACK ON Airbnb

WOOD BURNING FIREPLACE Sleeping arrangements-Walk out basement-there is a futon. main level living room and kitchen area top floor bedroom to the right has a king size bed and a futon two bedrooms to the left. One of the bedrooms has two full-size beds, and the other bedroom has a queen size bed, and a futon . Gorgeous Cabin! Fully sanitized& filled all essentials. Near many ski resort! Camelback, Elk Mountain, Jack Frost, Montage, and more! 20 min away from Woodloch Pines!

Top guest favorite

A scenic view of the river, showcasing lush green hills in the background and a collection of boats docked along the shore. A wooden deck is visible in the foreground, framed by a fence and greenery, inviting relaxation by the water.

Cottage in Sea Bright

4.95 out of 5 average rating, 133 reviews

Pineapple Cottage 1 Block to beach sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

Superhost

A serene lakeside view is captured from a wooden dock featuring two chairs, one white and one blue. The calm water reflects the cloudy sky and surrounding greenery, creating a peaceful atmosphere. Trees line the far bank, with hints of nearby residences visible in the distance.

Cottage in Nicholson

4.85 out of 5 average rating, 120 reviews

Lakeside Cottage near skiing/waterparks/wineries

Welcoming cottage located on a private lake near skiing, golfing, waterparks, wineries, and breweries. Recently renovated with a large living/dining area perfect for relaxing and gathering with family & friends. Offers an additional loft with 2 full-size beds, great for kids. A short walking distance from a year-round bar and grill with a rotating seasonal menu and craft beer. Several other casual and fine dining options are located within minutes.