
Holiday houses in Chester
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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!

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!

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.

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.

The Ember Cabin | Sky Cinema - Stargazing - Farm
Hilltop cabin on a working farm with boutique design. Curl up by the wood-burning fireplace in the Fireside Nook — a velvet sofa that converts to a queen bed. Upstairs, the Phoenix Sky Loft has 3 XL built in Twin beds, a 100" cinema screen, and galaxy ceiling projector. Spa bathroom with rain shower, copper farmhouse sink, fully equipped kitchen, in-unit washer/dryer. Stargaze from the outdoor net bed, grill at the fire pit, and visit our Highland Cattle & Babydoll Sheep. Sleeps 5.

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

“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.

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
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Highland Hideaway

The Grant Unit 2

Refurbished Rural Fire Station

Shirley's Place, Tiny Home on 40 Acre Farm

Off-grid cabin in the woods in Columbiana.

Guilford Lake House Cottage

Stony Oak Retreat #3

Historic Farmhouse Renewal
Destinations to explore
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Pittsburgh Holiday rentals
- Columbus Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- Baltimore Holiday rentals
- Richmond Holiday rentals
- Buffalo Holiday rentals
- PNC Park
- Carnegie Mellon University
- Acrisure Stadium
- Pro Football Hall of Fame
- University Of Pittsburgh
- David Lawrence Convention Center
- Pittsburgh Zoo & PPG Aquarium
- Gervasi Vineyard
- Raccoon Creek State Park
- Sri Venkateswara Temple
- Point State Park
- Kennywood
- Petersen Events Center
- Stage AE
- Phipps Conservatory and Botanical Gardens
- Moraine State Park
- National Aviary
- Schenley Park
- Carnegie Science Center
- Children's Museum of Pittsburgh
- Carnegie Museum of Art
- Senator John Heinz History Center
- PPG Paints Arena
- Randyland





