Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

A spacious bedroom is highlighted by a large metal bed with white bedding and decorative black and white pillows. A patterned rug covers the light wood floor. Natural light enters through a window, complemented by houseplants and stylish light fixtures. A small side table and decorative basket enhance the decor.

Apartment in Monaca

4.95 out of 5 average rating, 221 reviews

Key + Kin - Modern Industrial Farmhouse

Bring the whole family to this recently renovated home. This three story space has a layout perfect for group travel with friends or family. Our king-size bedroom and office are on their own floor, creating privacy for the second and third bedrooms are located on the top level. This stay is located on a quiet neighborhood street with off-street parking available, and a small park within walking distance — perfect for kids! We hope you book The Modern Industrial Farmhouse for your next getaway!

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, 257 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

4.93 out of 5 average rating, 150 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, 103 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

A contemporary home features a large deck surrounded by lush greenery. A prominent tree is seen in the front, providing natural shade. Adjoining the deck, red seating adds a pop of color against the earthy tones of the house.

Apartment in Salem

4.92 out of 5 average rating, 221 reviews

Rustic Retreat

Our Rustic Frank Lloyd Wright inspired contemporary home is located on 10 wooded acres amidst nature's beauty. There are trails in the woods for hiking & cross country skiing. The floor to ceiling walls of glass in the apartment bring the outside in and the private deck provides additional spectacular views of the woods. When not enjoying the wonders of the outdoors, take advantage of our included streaming services. We have a brand new heating and cooling system with 24/7 service!

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, 424 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

A warm living area features a tan leather sofa adorned with a striped throw pillow. A wooden coffee table sits nearby, decorated with a small green vase and a stack of books. Natural light is visible through the adjacent window, enhancing the inviting space.

Home in Chester

5 out of 5 average rating, 13 reviews

Historic Farmhouse Renewal

Welcome to our historic farmhouse renewal, a special project nestled in the picturesque countryside of Chester, WV. Just a short 23-mile drive from Pittsburgh Airport, this charming retreat offers a blend of a historic feel with modern comforts. Enjoy the barn view--a perfect backdrop for your morning coffee or winding down with a glass of wine. It's the perfect place to relax and rejuvenate with the tranquility of the countryside.

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

4.92 out of 5 average rating, 291 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.

Top guest favorite

A cozy living area is fitted with a brown couch and a matching recliner, complemented by a wooden coffee table. Ambient lighting is provided by two lamps. Soft carpet and wood-paneled walls create a warm environment, while framed artwork adds a touch of decor.

Guest suite in Salem

5 out of 5 average rating, 201 reviews

"Rest A While" spacious private suite

"Rest A While". Enjoy our private guest suite that features a large main living area where the kitchenette and dining area are also located, a separate bedroom and private bath. This suite is located on the lower level of our raised ranch and requires the ability to use six steps. Check yourself in at the private front entrance with keypad. Driveway parking spot with paved lighted walkway to the entrance.

Top guest favorite

A cozy bedroom features a full-size bed with fresh linens, a bright yellow accent blanket, and decorative pillows. The wall is painted in a warm yellow hue, complemented by blue accent decor. Shelves hold tasteful items, while natural light flows through the window adorned with soft curtains.

Apartment in Carnegie

4.91 out of 5 average rating, 148 reviews

Master Suite central to PGH and Airport Top 10%B&B

Welcome to Birds&Bees — Your cozy escape just 7 minutes from Pittsburgh! Unwind in this modern, pet-friendly retreat featuring a dreamy bed, comfy sectional, and a fully stocked kitchen with free snacks and drinks. Perfect for couples, solo travelers, or small families—comfort, style, and convenience all in one place. 📍 Ideal location 🐝 Themed interior 🐶 Pet friendly ✨ Modern touches

Guest favorite

A rustic log cabin is nestled in a lush wooded area, surrounded by greenery. Large windows allow natural light to fill the interior, while a stone fireplace enhances the exterior's charm. A spacious porch invites relaxation amidst the serene landscape.

Cabin in East Rochester

4.9 out of 5 average rating, 365 reviews

Cherry Ridge | Breezewood Cabins

This cabin is located in a 15-acre woods that is full of birds, deer, wild turkeys, and squirrels. This cabin is designed to be a perfect place to get away and find the rest and quietness we all need. It is intended to help you make memories, and reconnect with the person you love. We enjoy hosting and look forward to serving our guests in the best way possible!

Top guest favorite

A serene lake surrounded by lush greenery reflects a forested hillside and a charming red building. A small area of grass is visible along the water's edge, where guests can be seen enjoying the peaceful outdoor setting.

Home in Toronto

4.92 out of 5 average rating, 145 reviews

The Inn at Brandywine

Nestled in over 140 acres of wooded hills with a 5-acre, fully stocked, private lake, The Inn at Brandywine offers all the amenities of home in a relaxed, comfortable setting. Spacious, cozy, charming and well-equipped is what brings many guests back again and again. Secluded and private but just 3 miles from restaurants, gas stations and retailers.