Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
A functional kitchen area is complemented by wooden cabinetry and a countertop. A dining table with four chairs is positioned nearby, while appliances such as a refrigerator and stove are present. Natural light from a ceiling fixture illuminates the space, enhancing its cozy ambiance.
Flat in Chester
4.94 out of 5 average rating, 159 reviews

Lovely 1 bedroom duplex with free hi speed wifi

This 1 bedroom apt is centrally located between Pittsburgh PA and Youngstown OH just off Route 30 Lincoln Highway just 27 minutes from Pittsburgh Intl airport. A brand new Dollar General store within eyesight. Just 20 minutes to Monaca PA Cracker plant and just 15 minutes to Ergon or Shippingport PA Mountaineer is just 10-15 mins away. Easily sleeps up to 3-4 people. Both sides of duplex can be booked as long as not previously booked for your travel dates. 3 bar $ grills close by.

Top guest favourite
A fire pit is surrounded by log seating, set within a grassy area that opens up to lush greenery and tall trees. The sky is filled with scattered clouds, showcasing a peaceful outdoor environment ideal for relaxation and enjoying nature.
Cottage in Chester
4.98 out of 5 average rating, 110 reviews

Hillcrest Manor Cottage And Historic Wildlife Area

Welcome to Hillcrest Manor Cottage. A secluded hideaway tucked away on a hill above scenic woodlands. Soak in a private hot tub surrounded by 2,000 acres of forest & hills for hiking, hunting and fishing. Unite with nature and rejuvenate your spirit. * 8 Miles to Mountaineer Casino * 25 Minutes to The Pavilion at Star Lake * 30 Min. to Pittsburgh Airport (50 to City) * 5 Min. to Tomlinson Run State Park * 20 Min. to Beaver Creek State Park * Near Bars, Restaurants, Stores & Ohio River

Top guest favourite
The exterior of a recently renovated building is shown, featuring a combination of textured wood and painted surfaces. A spacious entrance with steps leads to the main door, while a well-maintained lawn and landscaping are visible. Parking areas are present on the side.
Guest suite in Monaca
4.98 out of 5 average rating, 193 reviews

Rivers Edge

Beautiful, quiet, downtown living with lots of windows. Full kitchen fully stocked for easy cooking and clean up with the dishwasher. All new fully renovated, everything is upscale, quartz countertops and custom easy close cabinets. Bathroom is spotless. Cable and WiFi for guests. A short two block walk to the river access, and 4 blocks to the boat dock access and pavillion. As close as you can get to the Shell Cracker Plant. This is a space that feels like home and is easy to relax.

Top guest favourite
A two-story house is set amidst greenery, featuring a brown exterior with a sloped roof and multiple decks. The building is positioned on a grassy area, complemented by gravel pathways and flowering plants in the foreground. A clear blue sky with scattered clouds is visible above.
Home in Weirton
4.98 out of 5 average rating, 100 reviews

The Retreat at Ralston

The Retreat at Ralston -- Nestled on a hillside down a private winding driveway, you'll find this peaceful country retreat. Located on 3.76 acres, the home offers an open floor plan with 2 bedrooms and 2 bathrooms. Double decks provide panoramic views. This home boasts high ceilings and skylights that allow natural light to reflect throughout each room. Features include a new hickory kitchen with quartz counter tops, updated bathrooms, and a bonus room downstairs featuring a pool table.

Top guest favourite
The cabin constructed from shipping containers is surrounded by greenery, featuring a covered patio with hanging planters. An outdoor seating area with Adirondack chairs and a fire pit is visible in the foreground, alongside a hot tub partially obscured by the building.
Shipping container in Lisbon
5 out of 5 average rating, 142 reviews

Shipping Container Cabin with hot tub!

Enjoy our secluded getaway, that's not too far away! This cabin is made from three combined shipping containers to create one memorable experience for our renters. Housed on ten acres on Beaver creek and surrounded by nature's beauty, this rental is sure to give you the adventure and relaxation you need. Enjoy your favorite drink on one of two beautiful patios, by the fire inside or out, and end your evening in the warmth of our hot tub. Only 6 minutes from Route 11 in Lisbon, OH!

Top guest favourite
A cozy living room features a dark sofa and an accent chair, arranged around a round coffee table. A flat-screen TV is mounted on a wooden shelving unit against the green wall, complemented by large windows allowing natural light to illuminate the space.
Home in Chester
4.93 out of 5 average rating, 56 reviews

The Auburn

Quiet, secluded home sitting on 3 acres. Observe the wildlife while sitting outside at this mountain retreat. Enjoy the large fenced in backyard with concrete fire pit area to roast those marshmallows or simply relaxing under the night sky with your friends or family. Inside, you will find a relaxing space to include 3 bedrooms, and 2 baths. Well equipped with necessary amenities and more, i.e flat screen tvs. Indoor and outdoor games also available during this peaceful retreat.

Superhost
Double glass doors are framed by flowing curtains, revealing a cozy bedroom space in the background. A decorative wreath hangs at the center of the doors, adding a gentle touch to the inviting entrance.
Home in Steubenville
4.9 out of 5 average rating, 116 reviews

The Cedar House

This 2 bedroom home sits on a friendly residential street in Steubenville and is equipped with everything you need for your stay. Two queen comfortable beds and pillows, professionally laundered with hotel style linens, a coffee bar, and three smart TVs and wi-fi. Close to everything in the Steubenville-Weirton area, including Franciscan University of Steubenville, hospitals in Steubenville and Weirton and The Pavilion at Star Lake amphitheater. You’ll feel right at home!

Guest favourite
An outdoor area features an oversized hot tub, complemented by a gas grill and two lounge chairs. The cabin's rustic log exterior is visible in the background, with trees providing a natural setting. A mix of cloudy skies and sunlight adds to the ambiance.
Cabin in Toronto
4.98 out of 5 average rating, 474 reviews

“Lil’ Cabin on the Hill” w Hot Tub and Pool Table

“Little Cabin” is a uniquely secluded hideaway perched on a private hillside setting. Warm and inviting, with indoor and outdoor areas of entertainment, the vibe is cozy and fun. Beautiful rustic interiors are highlighted with colorful modern design and comfort at every turn. Whether a getaway or business trip, your stay at “Little Cabin on the Hill” will be a memorable and welcome retreat. • • Gravel driveway is Steep with parking both at top and bottom of drive.

Guest favourite
A spacious living area is highlighted by a large, gray sectional sofa with a chaise. A wooden coffee table sits on a light area rug, complemented by two framed artworks on the white walls. Natural light filters through a window, creating a bright ambiance.
Home in Monaca
4.94 out of 5 average rating, 390 reviews

Key + Kin - Modern Rivertown Home

ENTIRE HOME, modern 2 Bedroom 1 Bath home centrally located in the small downtown Monaca area. Our warm, modern decor will be the perfect home away from home for you after a long day of work or play. We offer the privacy of a whole house, with little touches to make you feel at home. Come enjoy your own personal retreat in the heart of a quaint Pittsburgh river town.

Guest favourite
A log cabin is nestled among trees, featuring a welcoming porch with wooden railings. Circular windows provide natural light, and a stone chimney adds character. The forest surrounds the cabin, offering a serene and secluded setting.
Cabin in East Rochester
4.87 out of 5 average rating, 334 reviews

Oak Dale | Breezewood Cabins

This cabin is located in a 15-acre woods that is full of birds, deer, wild turkeys, and squirrels. This cabin is designed to be a perfect place to get away and find the rest and quietness we all need. It is intended to help you make memories, and reconnect with the person you love. We enjoy hosting and look forward to serving our guests in the best way possible!

Top guest favourite
A rustic cabin with a wooden exterior is showcased under a cloudy sky. The structure features a covered wrap-around porch with a railing, offering views of the surrounding farmland. Large windows are visible on the sides, enhancing the cabin's connection to nature.
Cabin in Carrollton
4.97 out of 5 average rating, 124 reviews

Rustic Serenity

Located on 80+ acres of woods and farmland, this rustic cabin is perfect for getting away from it all. Enjoy an evening by the fire, watch the sunrise over the treetops, see the deer graze on the hillside, do some bird watching, or stargaze without city lights to hinder. This is a place to truly unwind and disconnect from the hustle and bustle of city life.

Top guest favourite
A serene lake surrounded by lush greenery reflects a forested hillside and a charming red building. A small area of grass is visible along the water's edge, where guests can be seen enjoying the peaceful outdoor setting.
Home in Toronto
4.92 out of 5 average rating, 154 reviews

The Inn at Brandywine

Nestled in over 140 acres of wooded hills with a 5-acre, fully stocked, private lake, The Inn at Brandywine offers all the amenities of home in a relaxed, comfortable setting. Spacious, cozy, charming and well-equipped is what brings many guests back again and again. Secluded and private but just 3 miles from restaurants, gas stations and retailers.

Popular amenities for Chester holiday rentals

  1. Airbnb
  2. United States
  3. West Virginia
  4. Hancock County
  5. Chester