Holiday houses in Chester

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Top-rated holiday rentals in Chester

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

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Top Guest favourite
Home in Chester
4.98 out of 5 average rating, 109 reviews

Hillcrest Manor Cottage | Hot Tub | Near PGH

Hillcrest Manor Cottage sits on the edge of 2,212 acres of Hillcrest Wildlife Management Area — private, secluded, and surrounded by untouched West Virginia wilderness. Step outside to hunting, fishing, trails, wildlife watching, and complete seclusion, then return to your private hot tub under the stars. 30 min to Pittsburgh Airport, 25 min to Star Lake Pavilion, 8 miles to Mountaineer Casino, 5 min to Tomlinson Run, 20 min to Beaver Creek State Park. Near bars, restaurants, and the Ohio River.

Guest favourite
An open kitchen and dining area features wooden cabinets and appliances, including a refrigerator and stove. A round wooden table is surrounded by four chairs, and a ceiling fan provides light overhead. A doorway to the left leads to another space, enhancing the room's accessibility.
Apartment in Chester
4.92 out of 5 average rating, 170 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
The living space features rich wooden walls and a high ceiling adorned with large windows that allow natural light to fill the room. Comfortable seating is positioned to offer views of the river while a clock and light fixtures add subtle accents to the cozy atmosphere.
Cabin in New Cumberland
5 out of 5 average rating, 89 reviews

Cozy Cabin Nestled In The Hills

Escape to a cozy cabin with breath taking river views. This cabin features seclusion but still close to many amenities. Located minutes from a beautiful 18 hole golf course for the avid golfer. During the warmer months, enjoy the close proximity to the Ohio River. Spend your days boating, kayaking, or fishing. Feeling lucky? Take a ten minute drive to Mountaineer Racetrack and Casino to enjoy great food and games. Make a short drive to The Pavilion at Star Lake to see some big name concerts.

Guest favourite
A living room space features a dark brown sofa, a red armchair, and a rectangular coffee table. Two lamps provide soft lighting, and a large mirror reflects the area. The carpeted floor enhances the cozy ambiance, and the kitchen can be glimpsed in the background.
Apartment in Chester
4.95 out of 5 average rating, 38 reviews

The Quail House Main Level

Very private and quiet retreat atop a hill with amazing sunrises and sunsets. You’ll have the large backyard and deck all to yourself. This is an ideal space for three out of town workers and their mates to relax and grill at the end of a long day. The home is just 6 miles from Ergon and Mountaineer Casino and an hour from the Rivers Casino in Pittsburgh and Wheeling Island Casino and just 30 minutes from Pittsburgh International Airport. Non indoor smoking and pet free location please.

Top Guest favourite
A bright seating area features a vibrant yellow couch adorned with teal and patterned pillows. A coffee table sits at the center, surrounded by a colorful area rug. Natural light filters through sheer curtains, illuminating a decorative plant and wall-mounted television.
Home in East Liverpool
4.97 out of 5 average rating, 36 reviews

The Corner Store Retreat

A charming farmhouse-modern getaway in East Liverpool, Ohio, the Corner Store Retreat is a revitalized 1920s general store blending historic charm with modern amenities. Features include cozy, creative furnishings, a 6-foot swing, a coffee corner, an office with a printer, and a patio with a grill. Perfect for relaxation or adventure, with off-street parking, Wi-Fi, and a pet-friendly environment. Explore East Liverpool’s history through board games and enjoy a clean, comfortable stay!

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, 166 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!

Superhost
A cozy living area features a neutral-toned couch with decorative pillows, warmly illuminated by a soft lamp. A full-length mirror reflects the space. An entry leads to the bathroom, partially visible, with a tiled floor and basic fixtures. An artificial tree adds a touch of decor.
Home in Midland
4.89 out of 5 average rating, 109 reviews

Lovely 1/2 duplex

Enjoy our beautiful, quiet neighborhood. Within walking distance to PA Cyber and Lincoln Park Schools and a short drive across the bridge (no lights) to Bruce Mansfield or Shell cracker plant. 25 min to PGH Airport. 20 min to Geneva College. 40 min to downtown Pittsburgh. Newly renovated bathroom with comfortable furnishings. One block from Midland's walking track, the park, Midland pool, The Dollar General, Subway, Dairy Queen and laundrymat. Welcome to our convenient, cozy home.

Guest favourite
Cabin in Lisbon
4.95 out of 5 average rating, 101 reviews

The Rain House ~ Lisbon, OH

Slow down and recharge in this peaceful Japandi-style cabin tucked away in the rolling hills of Lisbon, Ohio. Designed with natural textures, clean lines, and calming tones, this 1 bed, 1.5 bath retreat invites deep rest. Enjoy the outdoor shower, private hot tub and scenic views. With high-speed WiFi, two TVs, a full kitchen, and laundry, it blends modern comfort with timeless serenity. Just minutes from Beaver Creek trails and cozy local eats. Ideal for couples or solo travelers.

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, 61 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.

Top Guest favourite
A spacious dining area features a handcrafted wooden table capable of seating eight. Natural light flows through large windows, providing a view of the outdoors. Accents include a modern chandelier and a cozy seating arrangement nearby. A smart TV is visible on the side.
Home in Toronto
5 out of 5 average rating, 55 reviews

130 Yr Old Whimsical Gem On 1.3 River Front Acres

Welcome to this thoughtfully remodeled 130 year old gem on 1.3 acres of river front seclusion. While this classic home is the perfect private get-a-way for you and your family, it’s location makes it easy for you to get around. You are only: 15 mins to Franciscan University 20 mins to Austin Lake 21 mins to William’s Country Club 28 mins to Star Lake Pavilion 29 mins to Mountaineer Racetrack & Casino 32 mins to Pittsburgh Airport 90 mins to the heart of Amish Country

Top 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, 498 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 features a textured sofa and coffee table, with a modern ceiling fan above. A dark brick accent wall hosts a flat-screen TV, while built-in shelves display decorative items. Natural light enters through the windows, enhancing the calm ambiance.
Apartment in Monaca
4.94 out of 5 average rating, 213 reviews

Key + Kin- Downtown Dwelling

Welcome to Key + Kin - Downtown Dwelling, a charming 1-bedroom, 1-bath apartment in the heart of downtown Monaca, PA. With warm modern decor and a prime central location, this updated space is perfect for couples, solo travelers, or business visitors. Enjoy an easy, walkable stay with restaurants, coffee shops, shops, and parks right nearby. A comfortable home base for exploring Beaver County, Pittsburgh attractions, or local work assignments.

Popular amenities for Chester holiday rentals