Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
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.
Flat in Chester
4.94 out of 5 average rating, 159 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 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.

Top guest favourite
A two-story house is set amidst greenery, featuring a brown exterior with a sloped roof and multiple decks. The building is positioned on a grassy area, complemented by gravel pathways and flowering plants in the foreground. A clear blue sky with scattered clouds is visible above.
Home in Weirton
4.98 out of 5 average rating, 101 reviews

The Retreat at Ralston

The Retreat at Ralston -- Nestled on a hillside down a private winding driveway, you'll find this peaceful country retreat. Located on 3.76 acres, the home offers an open floor plan with 2 bedrooms and 2 bathrooms. Double decks provide panoramic views. This home boasts high ceilings and skylights that allow natural light to reflect throughout each room. Features include a new hickory kitchen with quartz counter tops, updated bathrooms, and a bonus room downstairs featuring a pool table.

Top guest favourite
A private hot tub is situated on a patio, with bubbling water and soft lighting surrounding it. A stone pathway leads to a grassy area, framed by trees, creating a serene outdoor setting perfect for relaxation.
Home in Chester
4.98 out of 5 average rating, 110 reviews

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 hiking 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.

Top guest favourite
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, 148 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!

Top guest favourite
A charming cottage is situated by the serene Slippery Rock Creek, featuring a green roof and wooden deck. Surrounding vegetation includes tall trees, and reflections of the cottage are visible in the calm water. A spacious lawn offers a relaxed outdoor setting.
Cottage in Ellwood City
4.96 out of 5 average rating, 113 reviews

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.

Top guest favourite
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, 479 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 favourite
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, 33 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 favourite
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, 221 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 favourite
The spacious studio features original exposed brick walls and high ceilings with rustic wooden beams. Large windows allow natural light to illuminate the area. A dining table is centered, surrounded by comfortable seating, and a wall adorned with historical remnants is visible in the background.
Loft in Minerva
4.99 out of 5 average rating, 481 reviews

Luxury Brewery Loft | Steps to Taproom | King Bed

Nestled in downtown Minerva just two doors from Sandy Springs Brewing Co., The BQ is a luxury historic 1800s second-floor studio. Original brick walls, exposed beams, warm finishes, a copper kitchen sink, and a digital rain shower with body jets create a cozy yet elevated stay. Enjoy a king bed, leather chesterfield chair, and sleeper sofa. Walk to the brewery. Check-in beers included.

Guest favourite
A spacious living area is highlighted by a large, gray sectional sofa with a chaise. A wooden coffee table sits on a light area rug, complemented by two framed artworks on the white walls. Natural light filters through a window, creating a bright ambiance.
Home in Monaca
4.94 out of 5 average rating, 390 reviews

Key + Kin - Modern Rivertown Home

ENTIRE HOME, modern 2 Bedroom 1 Bath home centrally located in the small downtown Monaca area. Our warm, modern decor will be the perfect home away from home for you after a long day of work or play. We offer the privacy of a whole house, with little touches to make you feel at home. Come enjoy your own personal retreat in the heart of a quaint Pittsburgh river town.

Top guest favourite
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, 393 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 favourite
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, 156 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.

Popular amenities for Chester holiday rentals

  1. Airbnb
  2. United States
  3. West Virginia
  4. Hancock County
  5. Chester