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.

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Top guest favorite

A spacious bed dressed in soft linens is positioned against a neutral wall. A bedside lamp provides gentle illumination, while a small nightstand holds decorative items. A cozy armchair is situated nearby, enhancing the comfort of the private living space.

Apartment in Coraopolis

4.97 out of 5 average rating, 211 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.

Top guest favorite

A rustic log cabin showcases warm wooden siding and a red metal roof. The entrance is adorned with seasonal decor, including a wreath. A covered porch features a soft glow from an outdoor light. A gravel path leads to the cabin, supplemented by landscaping elements.

Cabin in East Palestine

4.95 out of 5 average rating, 273 reviews

Michelle’s Cozy Cabin A/C &Heat &Walking trail

Cozy cabin w/ A/C 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. 1/2 mile hiking trail 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

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.

Apartment in Chester

4.94 out of 5 average rating, 158 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

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

Guest favorite

A bright living room features a white sofa adorned with patterned throw pillows, two potted plants, and a wooden coffee table. Natural light floods the space through large windows, while a sliding barn door leads to a bedroom. Light hardwood flooring complements the modern decor.

Apartment in Monaca

4.96 out of 5 average rating, 239 reviews

Key + Kin - The Uptown Place

Tucked into the heights of charming Monaca, PA, this freshly renovated unit is minutes away from restaurants and shops. Wake from your slumber in one of the two spacious and modern bedrooms adorned with a cozy reading nook or work from home space, full length mirrors, and gorgeous natural light. Make your way into the bright kitchen for a cup of coffee, and snuggle up on the couch in the living room as you take in the day. Welcome to your private abode to unwind and relax during your trip.

Top guest favorite

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, 116 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 favorite

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, 98 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

The image showcases a three-story home with a light grey exterior and blue accents, featuring a prominent gabled roof. A wooden deck with a railing extends in front, providing an inviting entryway. The neighborhood architecture is visible in the background.

Apartment in Pittsburgh

4.98 out of 5 average rating, 171 reviews

Cute Apt Minutes from Downtown and Stadiums!

🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

Guest favorite

A cozy bedroom is presented with a wooden bedframe, dressed in layered bedding. Twin nightstands are positioned on either side, with a lamp on one. A ceiling fan and wall-mounted air conditioning unit add comfort, while a framed artwork enhances the wall above the bed.

Home in Conway

4.96 out of 5 average rating, 129 reviews

Charming Renovated Home

This centrally located house is close to the communities of Cranberry Township, Pittsburgh, and Sewickley. Our home has been completely renovated from top to bottom and is pristine condition. An open concept design is offered on the main level connecting the dining room, living room, and fully equipped kitchen. Also on the main level is a half bath for your convenience. Upstairs you will discover a full bath and 2 cozy bedrooms with beautiful vaulted beamed ceilings.

Top guest favorite

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, 452 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 favorite

The living area features a comfortable gray sofa with light cushions, alongside a wooden table set for four. A modern kitchen bar with high stools is visible in the background. Natural light fills the space through the sliding door, adding warmth to the hardwood floors.

Home in Chester

4.97 out of 5 average rating, 30 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.

Top guest favorite

A cozy living area features a round wooden dining table with four chairs and a patterned couch. The kitchenette is backed by wooden cabinetry, with appliances visible. Light filters in through a window, highlighting the slanted ceiling and creating an inviting atmosphere.

Guest suite in Steubenville

4.93 out of 5 average rating, 313 reviews

The Loft in Steubenville

This efficient guest suite is located in the heart of Steubenville (17 miles/20 min. from Star Lake Pavilion). Separated by a hill from our family home, the loft provides a simple place to rest after a long day of travel, work, conferences, or whatever may bring you to Steubenville! We built this guest space above our work garage with visiting family in mind, and we hope you'll feel equally at home as our guest.