Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
Flat in Chester
4.93 out of 5 average rating, 161 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 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, 102 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
Home in Chester
4.98 out of 5 average rating, 110 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 hiking 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.

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, 150 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!

Guest favourite
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
4.91 out of 5 average rating, 102 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.

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, 57 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 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, 113 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.

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, 480 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 light-filled living area features a white brick fireplace as a focal point. Comfortable seating, including a sofa and armchairs, surrounds a wooden coffee table. Natural light enters through large windows, partially adorned with soft curtains, enhancing the spacious feel of the room.
Home in Monaca
4.95 out of 5 average rating, 309 reviews

Key + Kin - The Oasis

Welcome to your oasis! This newly renovated home features light and bright rooms, outfitted with cozy touches sure to help you relax as soon as you enter. The private, fenced backyard hosts with a covered patio, pergola, pristine pond and swing. Inside the home, you will find sweet pockets of peace in the private living room, and second floor office and bedrooms. Tucked on a quiet street, the location can't be beat! Come discover the hidden gem of Monaca, PA

Top guest favourite
The exterior of a log cabin is presented, featuring a green metal roof and wooden pillars supporting a covered porch. Seating areas are arranged outside, surrounded by grass and lush trees, providing a serene and secluded environment.
Cabin in East Palestine
5 out of 5 average rating, 117 reviews

Michelle’s Log Cabin @ Horse Farm

Secluded and peaceful, with all the amenities of home. Enjoy a relaxing getaway in a log cabin Treats provided for horses . 1/2 mile walking trail loop Comcast WIFI, fire ring, gas grill, 3 TV’s . Super clean! Incinerator toilet Enjoy the sunrise over the pasture. *Please book for number of people on property *Must check/pay for pet at booking *Must keep off furniture/bedding! I look forward to making your visit, pleasant and memorable 🌸

Top guest favourite
Home in Monaca
4.97 out of 5 average rating, 104 reviews

Rivers Edge Retreat

Modern, spacious home on the best street in town. Quiet, safe, and perfectly walkable to restaurants, cafés, shops, parks, and river access. Fully remodeled with granite counters, custom cabinets, large windows, fast WiFi, smart TV, full laundry, and a private driveway. Enjoy two private bedroom suites with comfortable beds, ideal for families, couples, work trips, or weekend getaways seeking convenience and style.

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, 481 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.

Popular amenities for Chester holiday rentals

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