Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

A spacious sleeping area features a memory foam bed, adorned with a patterned quilt and coordinating pillows. A bedside table with a lamp provides soft lighting, while a cozy area rug complements the room. A fireplace adds warmth, enhancing the serene ambiance.

Apartment in Chester

4.89 out of 5 average rating, 19 reviews

Quail House Studio

No stairs required as you enjoy amazing sunrises and sunsets at this serene, NON SMOKING AND PET FREE, 16 acre property. YOU WILL NEED 4WD in winter. The apartment is just steps away from your parking space. You just may see deer, fox, turkeys, rabbits and more. This is a great place to rest and ease the mind and an ideal location for gambling enthusiasts as the casino is just six miles away! This location is convenient for an out of town worker or couple who don’t want a hotel based stay.

Top guest favorite

Cabin in New Cumberland

5 out of 5 average rating, 34 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.

Top guest favorite

A television remote control is placed on a light-colored wooden surface. The remote features buttons for popular streaming services such as Netflix, Disney, and Hulu. A portion of a black microwave is visible in the background, suggesting the kitchen setting.

Apartment in Chester

4.93 out of 5 average rating, 129 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 walking. Brand new mattress Jan ‘25 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 date

Top guest favorite

Two comfortable seating areas are positioned around a stone fire pit, set in a spacious grassy clearing. Lush trees surround the area, creating a serene atmosphere. Blue skies and scattered clouds provide a peaceful backdrop, highlighting the cottage's secluded wilderness.

Cottage in Chester

4.98 out of 5 average rating, 92 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 favorite

Cabin in East Palestine

4.94 out of 5 average rating, 247 reviews

Michelle’s Cozy Cabin,Walking trail, Sauna

Cozy cabin tucked in the woods on my 9 acre farm. Overlooks pasture with horses. Horse treats provided. No running water but 2 five gallon jugs provided Showers available at main house. Also water available at spigot behind log cabin. Incinerator toilet. Designated hiking trails on property surrounding the pasture Great WI-FI/ cell svc, High speed internet and 32”TV with Netfix Heat and A/C Infrared sauna If bringing a pet, please check pet at booking and be mindful of cleanliness

Guest favorite

A large television is positioned beside a dresser, displaying various streaming options. The adjacent room is visible through an open doorway, featuring a dining area with a dark table and white chairs, illuminated by natural light from a nearby window.

Home in Midland

4.92 out of 5 average rating, 83 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 favorite

A spacious front porch features a cozy swinging seating area, surrounded by comfortable wicker chairs and tables. The area is decorated with a natural fiber rug, creating an inviting space filled with ample sunlight and greenery from nearby plants.

Home in Toronto

5 out of 5 average rating, 35 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

Guest favorite

The exterior of a log cabin is displayed, showcasing rustic wooden siding and a green metal roof. A small covered porch is visible with outdoor furniture, including rocking chairs. The surrounding gravel area offers space for relaxation, and the hillside is lined with trees in the background.

Cabin in Toronto

4.98 out of 5 average rating, 394 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 favorite

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, 267 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 favorite

Home in Ambridge

4.97 out of 5 average rating, 156 reviews

Historic District Comfort

Keep it simple, go back in time, at this peaceful and centrally-located private residence. An Old Economy Gem overlooking the courtyard, on a one-way street in the heart of the Historic Old Economy in Ambridge, Pa. Quiet and quaint, this home has been redone back to its original finishes with upgrades on all new infrastructure and appliances. Conveniently located just off Route 65 North, 16 miles from downtown Pittsburgh, direct and easy commute.

Top guest favorite

A small outdoor balcony features a round table and two bright green chairs, creating a cheerful seating area. Sunlight casts striped shadows across the wooden floor, with a salt lamp displayed on the table. The surrounding trees and greenery enhance the serene environment.

Home in Chester

5 out of 5 average rating, 11 reviews

Piedmont

Welcome to Piedmont! An almost new 2 bedroom, 1.5 bath cabin sitting on 2 acres far away from it all, but still driving distance to anything you may need. So come observe the wildlife and relax at the Piedmont! Inside, you will find a relaxing space to include 2 bedrooms, and 1.5 baths. Well equipped with necessary amenities and more, i.e flat screen tvs. Indoor and outdoor games also available during this peaceful retreat. No cleaning fee

Top guest favorite

A dining area features a wooden table topped with round place mats and minimalist tableware. A small vase holds fresh flowers, and a wall clock adds a touch of decor. A bright door allows natural light to enter the space.

Apartment in Beaver

4.94 out of 5 average rating, 202 reviews

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

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Other great vacation rentals in Chester

Guest favorite

A spacious deck features comfortable seating with plush cushions, complemented by a nearby grill for barbecues. Planters with vibrant flowers and fresh basil add a touch of greenery, while a serene view of surrounding trees enhances the outdoor setting.

Private room in Beaver

5 out of 5 average rating, 12 reviews

Hawkins Haven

PattiRating, 5 stars1 week ago

Valarie’s place was continently located close to downtown Beaver. Valarie and David were very kind. They were gracious and willing to help in any way.

Top guest favorite

Private room in Pittsburgh

4.98 out of 5 average rating, 571 reviews

Basement apartment with private entrance and bath

NourRating, 5 stars4 days ago

Michaels place felt right at home. The space was cozy and comfortable. My husband and I appreciated Michaels clear instructions, suggestions , and quick communication. I really enjoyed the snack options and as always, can never beat a massage chair. I highly recommend Michaels space. It was clean, cozy, and felt right at home. :)

An outdoor seating area features a dark blue sectional sofa arranged around a small wicker table. The space is surrounded by a fence, with a clear view of a shed and nearby houses against a soft morning sky.

Apartment in Midland

4.87 out of 5 average rating, 31 reviews

Feeling at home when you're away from home!

TroyRating, 5 stars5 months ago

Great hosts would stay again when I’m in town for business

Guest favorite

A charming two-story home is showcased under a vibrant sunset sky. The exterior features a light gray facade, white trim, and a welcoming front porch with steps leading up. A well-manicured lawn adds a touch of greenery, complemented by surrounding trees.

Home in Beaver Falls

5 out of 5 average rating, 7 reviews

Spare Oom of Beaver Falls

DaveRating, 5 stars2 weeks ago

Ruth’s “Spare Oom” is absolutely adorable. There’s not a ton of space, so it’s cozy. But the layout and furniture selection is perfect. This was the perfect place to stay for a weekend at the racetrack.

A compact bathroom is featured, showcasing a toilet and a small sink. A decorative shelf is mounted on the wall above the toilet, holding personal items. The floor displays black and white tile in a hexagonal pattern, complementing the earthy wall color.

Home in Lisbon

5 out of 5 average rating, 4 reviews

Pippy’s Pretty Brick Palace

KimRating, 5 stars3 weeks ago

This historic home is a gem! Four bedrooms with plenty of space to relax with a large family. All the bedrooms are all on the second floor together with a full bathroom, which we loved. The home is beautifully decorated and has so much character! Pam gave us great local recommendations and responded quickly with questions. Lisbon had great restaurants as well! We can't wait to come back!

A garage door with a smooth white surface is situated alongside a smaller white door. The structure is framed by natural wood accents, and the surrounding area features a gravel surface and landscaped features, providing access to the house.

Home in East Liverpool

4.65 out of 5 average rating, 17 reviews

Cheerful, 2 Bedroom home, free private parking

ErinRating, 5 stars6 months ago

Jennifer’s place was lovely. We had to shorten our trip due to bad weather but would have happily stayed longer. The kitchen was well equipped, we slept well in comfy beds, and it was neat to wake up and realize the neighbors had a donkey.

The spacious living area features an open floor plan with large windows allowing natural light to fill the space. Two dark armchairs are positioned around a contemporary coffee table, set beneath a modern light fixture. A subtle wooden ceiling adds warmth to the room.

Home in Weirton

4.66 out of 5 average rating, 155 reviews

Unique and Secluded Country Estate near Pittsburgh

JohnRating, 5 stars3 days ago

This was our second stay. It was better this time than an excellent first trip. Physical space was improved. Great beds! We told others to book if they needed accommodations in the future. First class place in an area of the country where that level is difficult to find.

Guest favorite