Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
The exterior of a pre-1900's farmhouse is showcased, featuring a welcoming front porch with seating and vibrant landscaping. The two-story house has light-colored siding and a brick foundation, surrounded by greenery and trees, offering a serene country setting.
Farm stay in Carrollton
5 out of 5 average rating, 204 reviews

Hidden Hollow Farmhouse

Enjoy the quiet simple life of the country on a working farm. This spacious pre-1900’s farmhouse is quaint, quiet and wholesome. Come as a family and friends looking to regenerate and escape the fast pace of life and disconnect from technology. There is no WiFi, there is cell service for calls/texts. A TV/DVD player, no TV service. No need, nature and the peace of the farm will fill your bucket. The farm has a pond with fishing and trails for hiking with an abundance of fresh air and nature.

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.
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
The exterior of a rustic loft apartment is displayed, featuring a wooden facade and a stone base. Large windows allow natural light to fill the space, while a balcony offers outdoor access. The structure is set against a backdrop of a partly cloudy sky.
Loft in East Rochester
4.93 out of 5 average rating, 163 reviews

Studio Loft at Boogaba

This space is totally new! It was a yoga studio recently renovated into a studio, loft apartment! It is airy and bright with a fantastic lake view. The lake has kayaks, paddle boarding and a peddle boat that are accessible to guests. There are walking paths around the lake and a deck with a hammock to sit and enjoy some nature time. The studio apartment has its own entrance in the back above the family garage. The family house is next door. There is a resident friendly yellow dog named Pug!

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 charming cottage is situated by the serene Slippery Rock Creek, featuring a green roof and wooden deck. Surrounding vegetation includes tall trees, and reflections of the cottage are visible in the calm water. A spacious lawn offers a relaxed outdoor setting.
Cottage in Ellwood City
4.96 out of 5 average rating, 110 reviews

Cozy Cottage nestled on the Slippery Rock Creek

Secluded along the banks of the Slippery Rock Creek is the 4th generation family cottage, fully renovated in 2017, originally built in 1940. Descend the 45 steps to the cottage and find “there’s no place like (a 2nd) home”. From the wraparound deck you may see geese, deer, bald eagles, osprey, beaver, great blue heron and ducks. You will find yourself just 15 minutes from Moraine and McConnells Mill State Parks. 15 minutes from Mines and Meadows, 10 minutes from Sunset Ranch.

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, 472 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.

Top guest favourite
The spacious studio features original exposed brick walls and high ceilings with rustic wooden beams. Large windows allow natural light to illuminate the area. A dining table is centered, surrounded by comfortable seating, and a wall adorned with historical remnants is visible in the background.
Loft in Minerva
4.99 out of 5 average rating, 479 reviews

Luxury Brewery Loft | Steps to Taproom | King Bed

Nestled in downtown Minerva just two doors from Sandy Springs Brewing Co., The BQ is a luxury historic 1800s second-floor studio. Original brick walls, exposed beams, warm finishes, a copper kitchen sink, and a digital rain shower with body jets create a cozy yet elevated stay. Enjoy a king bed, leather chesterfield chair, and sleeper sofa. Walk to the brewery. Check-in beers included.

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.

Popular amenities for Chester holiday rentals

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