
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Oculus Tinyhouse at Innisfree Farms
Innisfree Farms is a rural retreat in northern West Virginia with five dwellings on a 70-plus acre farm. The Oculus is the perfect country getaway for solos or couples. Everything you'll need and nothing you won't, including a comfy bed, a beautiful view, full facilities, and the great outdoors. Near Oglebay Park and Wheeling - but private, pet-friendly, and welcoming to all. One cozy bed - a perfect spot to read, hike, think, or just enjoy a campfire and the natural setting. Check our reviews!

Moon Professional Living Suite B
Recently updated 1 bedroom 2nd floor efficiency apt. w/ everything you will need for a comfortable stay. We do have 2 Airbnb Apartments available. We follow all Airbnb standards to provide a safe, quiet, sparkling clean, comfortable experience for all & ask you do the same. Minutes from the airport & short drive to downtown Pittsburgh. Shopping & dining nearby. Perfect for out of town guests & business travelers. Live far from the airport & have an early flight? Come stay at Cozy in Coraopolis.

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.

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!

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.

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.

“The Henry” House with Private Hot Tub
A picturesque countryside getaway with the convenience of shopping and restaurants nearby. If you love breweries, hot tubbing, golfing, cruising the neighborhood in a Model T golf cart, or just relaxing in a really cool house, this place is for you! Antiquing and open summer concerts minutes away. Comfort awaits with beautiful cozy interiors and a vintage vibe. With a touch of history and a lot of charm, your stay at “The Henry” will be a fun and welcome retreat.

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

Magnolia Cozy Cottage
A discount price for weekly & monthly bookings. If you plan to stay longer than a month a special rate can be given. Enjoy the entire apartment with all the amenities of home. The place is very clean . Enjoy your own private entrance and parking. The living room is equipped with leather couch, large screen screen TV and fireplace. There is a full bathroom with a full tub and shower. The bedroom has a queen size bed

Secluded Tiny “Ginseng House” Artist Retreat
"Ginseng House" - Our premiere off-grid tiny house! A hand-crafted work of art using our own sawmill lumber. Beautiful wooded setting surrounded by 180 acres of private land and two miles of beautiful Buffalo Creek frontage to enjoy. One very comfortable queen bed in the loft and a fold out double bed love seat on the main floor. Extra guests may pitch tents for $10/night/person. Pets welcome - $35/pet - see pet policy.

Hemlock House, Modern 2BR near Pittsburgh
Escape to Hemlock House — a historic farmhouse in the serene countryside of Baden, PA — just 30 minutes from Pittsburgh and 15 minutes from Cranberry Township. Two bedrooms, three beds, one bathroom, full kitchen. Ideal for writers, artists, couples, families, or solo travelers seeking a peaceful getaway. Enjoy nearby attractions like Moraine State Park and McConnells Mill, or explore local dining and breweries.
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester

Highland Hideaway

The Grant Unit 2

Spacious 2br

Off-grid cabin in the woods in Columbiana.

The “Dreamcatcher” Treehouse with Private Hot Tub

Newly Remodeled+Fam Friendly +Convenient to Univ

Cheerful, 2 Bedroom home, free private parking

Little Cabin On The Lake
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Washington Vacation rentals
- Mississauga Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- Northeast Ohio Vacation rentals
- Grand River Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Pittsburgh Vacation rentals
- Rappahannock River Vacation rentals
- PNC Park
- Carnegie Mellon University
- Acrisure Stadium
- Pro Football Hall of Fame
- David Lawrence Convention Center
- University Of Pittsburgh
- Pittsburgh Zoo & PPG Aquarium
- Gervasi Vineyard
- Raccoon Creek State Park
- Sri Venkateswara Temple
- Point State Park
- Kennywood
- National Aviary
- Phipps Conservatory and Botanical Gardens
- Schenley Park
- Stage AE
- Petersen Events Center
- Children's Museum of Pittsburgh
- Carnegie Science Center
- Carnegie Museum of Art
- Cathedral of Learning
- Senator John Heinz History Center
- Randyland
- PPG Paints Arena





