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Chester Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Chester Vacation Homes

Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Enjoy cooking in this well-equipped kitchen with a central island and dishwasher.

Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh

10.0 out of 10, Exceptional, (14)
"Perfect location and charming feel"
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Kitchen features a stainless steel range hood, oven, and large refrigerator, along with white cabinetry and a wooden floor.

Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village

9.8 out of 10, Exceptional, (7)
"We truly enjoyed our stay at this comfortable home in Sewickley Village! Everything worked out perfectly and walking around town so easily due to the convenient location was ideal!"
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Unique and Secluded Country Estate near Pittsburgh
Relax in a spacious interior with a sofa, chairs, and dining table, surrounded by large windows and exposed wooden beams.

Unique and Secluded Country Estate near Pittsburgh

8.0 out of 10, Very good, (5)
"We enjoyed our holiday stay here. Beautiful home. "
Unique and Secluded Country Estate near Pittsburgh
Orchard House
Enjoy a peaceful stay in this single-story house with a front porch and a spacious wooden deck.

Orchard House

9.8 out of 10, Exceptional, (7)
"The house was beautiful and clean"
The price is CA $162
CA $380 total
includes taxes & fees
Aug 12 - Aug 13
Orchard House
Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville
Cozy retreat with a large bed, nightstand, and framed picture.

Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville

9.0 out of 10, Wonderful, (4)
"Large yard with fire pit , fawns and rabbits "
Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville
Cozy little Castle. Warm & welcoming.
Modern kitchen with a granite countertop, stainless steel sink, oven, and wooden cabinets.

Cozy little Castle. Warm & welcoming.

9.2 out of 10, Wonderful, (21)
"Came up to celebrate our daughters 21st birthday. This is a great location: close to campus, close to food options, and close to shopping. This is our second time staying at this location we have not been disappointed yet."
Cozy little Castle. Warm & welcoming.
House at Maple Ridge
Enjoy meals and socializing around the central island with seating and ample counter space.

House at Maple Ridge

10.0 out of 10, Exceptional, (26)
"Lots of space to spread out. Great fun with the pingpong and pool and hiking path! Beautiful place!"
House at Maple Ridge
COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!
Enjoy al fresco dining on the deck with a picnic table and bench surrounded by lush greenery.

COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!

9.8 out of 10, Exceptional, (7)
"We needed a place for a single night for a school event . We traveled 5 hrs to find a wonderful place for us to nestle down for the evening. Was spacious, clean , perfect size for us . Had every amenity we need and then some,. Great location and the town ow Sewickley near by had great people , food and dessert. We loved it . Would highly recommend "
The price is CA $140
CA $278 total
includes taxes & fees
Aug 25 - Aug 26
COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!
Cozy Home outside Pittsburgh
Kitchen area with stove, sink, and seating area with sofa and TV.

Cozy Home outside Pittsburgh

10.0 out of 10, Exceptional, (7)
"Great Stay"
Cozy Home outside Pittsburgh
Charming, Modern & Cozy Home
Enjoy cooking in this well-lit kitchen with sleek cabinetry, a stove, and a brick backsplash.

Charming, Modern & Cozy Home

8.6 out of 10, Excellent, (4)
"Felt like home for almost a week. "
Charming, Modern & Cozy Home
Royal Garden Cottage
Outdoor dining

Royal Garden Cottage

The price is CA $160
CA $301 total
includes taxes & fees
Aug 12 - Aug 13
Royal Garden Cottage
Charming Hotel Rooms w/ bar, pool tables, dart board and restaurant downstairs
Enjoy dining or meeting in this stylish indoor space with large windows offering a view of the outside.

Charming Hotel Rooms w/ bar, pool tables, dart board and restaurant downstairs

10.0 out of 10, Exceptional, (2)
"Loved Skylar at check in. Rooms are quaint and the area is nice. "
The price is CA $89
CA $160 total
includes taxes & fees
Aug 12 - Aug 13
Charming Hotel Rooms w/ bar, pool tables, dart board and restaurant downstairs
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi
Interior

Spacious 5-bedroom house in delightful Stubenville with AC, WiFi

8.0 out of 10, Very good, (4)
"The home was cute, clean and central to all locations on our agenda."
The price is CA $241
CA $316 total
includes taxes & fees
Aug 19 - Aug 20
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi
Cozy home away from home. Located in Steubenville.
Stunning two-story home with a central entrance and beautifully manicured grounds.

Cozy home away from home. Located in Steubenville.

9.2 out of 10, Wonderful, (33)
"Older rough but quiet neighborhood. Clean older home with 2 bathrooms a big plus, comfortable beds. Would stay again! "
Cozy home away from home. Located in Steubenville.
Near Mines & Meadows: Spacious Home w/ Game Room
Enjoy a serene view from this outdoor space with a well-maintained lawn and tall trees.

Near Mines & Meadows: Spacious Home w/ Game Room

9.6 out of 10, Exceptional, (15)
"Clean, spacious property. Well-equipped for hosting large groups. Great communication throughout our stay. Would rent again!"
Near Mines & Meadows: Spacious Home w/ Game Room
The Piedmont Cabin - LPM
Fridge, microwave, oven, stovetop

The Piedmont Cabin - LPM

2.0 star property
The price is CA $206
CA $276 total
includes taxes & fees
Aug 17 - Aug 18
The Piedmont Cabin - LPM
Beautiful Log House in Cranberry
Cozy cabin with a stone fireplace, wooden furniture, and a mounted TV.

Beautiful Log House in Cranberry

9.8 out of 10, Exceptional, (8)
"Perfect size and location for our purpose. We recommend it!"
The price is CA $333
CA $790 total
includes taxes & fees
Aug 12 - Aug 13
Beautiful Log House in Cranberry
Charming 3-bedroom house with AC and WiFi in a very convenient location
Exposed ductwork and construction materials fill this unfinished basement area, featuring a high ceiling and a door leading to another room.

Charming 3-bedroom house with AC and WiFi in a very convenient location

2.0 star property
8.8 out of 10, Excellent, (3)
"Juliet is an excellent Host. Very Amicable and Friendly."
Charming 3-bedroom house with AC and WiFi in a very convenient location
Like new Cozy townhome with home office in Beaver Falls, near Pittsburgh
Enjoy cooking in this well-equipped kitchen with a large island and stainless steel appliances.

Like new Cozy townhome with home office in Beaver Falls, near Pittsburgh

10.0 out of 10, Exceptional, (2)
"Great location for us to get to Brady Park for an event. "
Like new Cozy townhome with home office in Beaver Falls, near Pittsburgh
Modern Farmhouse in town.
Situated in a lush lawn area, this serene setting features a picnic table under a large tree's shade.

Modern Farmhouse in town.

10.0 out of 10, Exceptional, (8)
"We were in the area for a family reunion and loved staying here. It was perfect for what we needed!"
Modern Farmhouse in town.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Sheraton Pittsburgh Airport Hotel

Sheraton Pittsburgh Airport Hotel

10/10 Excellent
"Everything was nice except for the pool area. It was unkept with a few pieces of trash and a two used towels laying around. "
Scott 1-night trip
Posted 1 day ago
Sheraton Pittsburgh Airport Hotel