Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. A central island with two red stools provides a casual dining area, while white cabinetry and a sparkling chandelier enhance the bright, welcoming atmosphere.

Home in Steubenville

4.89 out of 5 average rating, 150 reviews

El Villa on Efts

Located 7 minutes away from Franciscan University and 15 minutes from Key Bank pavilion (Starlake) Where wildlife roam free and relaxation takes over, El Villa on Efts is the place for you. If you are looking for an extended stay or a quick get away, this charming villa is just what you need. Grab a good book or a cocktail and prepare to make memories around the bonfire or in the screened in porch. If you love the outdoors but not the mosquitos, enjoy your night on the screened in porch instead!

Guest favorite

An expansive outdoor deck features a sectional seating area with soft cushions, a coffee table, and a dining set. A fire pit with adjacent seating is visible, along with a patio heater. Potted plants add greenery to the space, enhancing the tranquil atmosphere.

Apartment in South Side Flats

5 out of 5 average rating, 8 reviews

Wow! Skyline Sunset Escape On Hackstown

Ahoj and welcome to your elegant 2-bed, 1.5-bath home with breathtaking downtown views! Newly renovated with a thoughtfully designed interior, this home offers a distinctive experience. Enjoy parking in a 2-car garage plus an outdoor space, and easy access to downtown and Oakland. Featured on the South Side Historic Homes Tour, it’s a true Pittsburgh gem. Pets are allowed! Relax on the deck with a fire pit, or unwind by the custom mosaic fireplace with a 55” TV or in the luxurious soaking tub.

Superhost

A spacious living area showcases a sectional couch, paired with a sleek side table. The room features vaulted wooden ceilings and large windows that provide views of the outdoors. A patterned area rug is positioned on the floor beneath, enhancing the inviting ambiance.

Home in Murrysville

4.88 out of 5 average rating, 121 reviews

Gorgeous Modernized Cabin + Hot Tub + Pool Table

Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

Guest favorite

A charming cabin is nestled among lush greenery, offering a welcoming porch with seating. The structure features a metal roof and an outdoor grill. A gravel driveway leads to a covered parking area, enhancing the convenience for guests arriving by car.

Tiny home in Scio

4.91 out of 5 average rating, 270 reviews

Cozy Cabin

SMK Cabin Rental is a cozy little cabin located 1.5 miles from Tappan Lake. 2 open loft style bedrooms upstairs. Kitchen, bathroom and living room downstairs. Central air and central heat. Dish tv. hot tub Gas grill and a firepit. Located on our own 12 wooded acres. Guests are more than welcome to enjoy a hike in our woods to enjoy the nature. We are not a 5 star resort nor do we try to be. We are a camping cabin. You may encounter wildlife deer, raccoon, bugs, etc on your trip..

Top guest favorite

A private deck area is visible, featuring a woven chair and a patterned rug. Beyond the deck, a green lawn extends towards a distant blue house, framed by trees. Clear skies are overhead, enhancing the tranquil outdoor setting.

Cottage in Mercer

4.99 out of 5 average rating, 104 reviews

Charming Farm Cottage

Relax with the whole family at this peaceful homestead cottage nestled among mature pines. Scenic views and tasty natural treats abound on the guest house of this 6 acre homestead. Enjoy an evening by the wood stove or watch the sunrise from the pet friendly deck. Ask about lawn games or access to pool and spa attached at the owners' residence down the lane. Located minutes away from fishing lakes, colleges, state parks, game land, and Downtown Mercer. Easy access from I-79, I-80.

Guest favorite

An outdoor deck area features a dining table surrounded by four metal chairs, set against a backdrop of lush greenery. The space is illuminated by natural light, creating a serene environment that connects with the surrounding trees and landscape.

Home in Warren

5 out of 5 average rating, 5 reviews

Serene Retreat Near The Grand Resort

Welcome to your spacey and eclectic oasis, nestled conveniently near The Grand Resort! Sink into luxurious bedding and let the dreamscape surroundings transport you to a world of relaxation. The outdoor area is a true gem, featuring a lush garden and a variety of seating options that invite you to unwind and bask in the serenity. Whether you're sipping your morning coffee or enjoying a glass of wine under the stars, this space offers a perfect balance of nature and comfort.

Guest favorite

A serene view of the lake is presented, with lush greenery framing the scene. A large tree stands prominently, while the calm water reflects the surrounding nature. In the distance, various boats and lakeside structures are visible, enhancing the tranquil atmosphere.

Home in Lake Milton

4.82 out of 5 average rating, 88 reviews

Scenic Shores Guest Lake House with dock.

Cheerful 3 bedroom cottage just steps away from the lake. Enjoy the easy access to everything from this perfectly located home base. Boat dock is about 100 feet from house and is available upon request. We had storm damage and lost part of our fence. Missing panels are on order and will be replaced soon. Great water views. The home has 3 bedrooms which sleeps 6 (plus a pull-out sofa in the living room $50/per extra guest over 6, with a limit of 8 total guests).

Top guest favorite

Cottage in Mercer

4.98 out of 5 average rating, 62 reviews

Mermaid Inn romantic house on the lake

Gorgeous house on the private lake with King master suite and minutes away from shopping (Prime Outlets), dining ( large restaurant selection), wining (winery) and skydiving ( local airport one mile away) , the house has beautiful woods for hiking and private lake for kayaking and fishing. Located only 5 min away from Rt79 it feels like it’s completely removed from hustle and bustle of modern life. Fully equipped kitchen and beautiful views

Guest favorite

An outdoor bar area is showcased under a wooden structure, featuring four high-backed stools positioned around the bar. A grill is present nearby, with a wall-mounted TV visible above the bar, framed by lush greenery from the surrounding trees.

Home in Alliance

4.9 out of 5 average rating, 179 reviews

Beautiful Lakefront House on Berlin

The perfect getaway for your large or small gathering. Relax at our outdoor bar and hot tub, perfect for a adult getaway or a family weekend. Overlooks the lake for beautiful sunsets. Looking for an adventure? Canton air sports is just across the road, or just enjoy watching someone else sky dive right above the house. Only miles from the highway and many restaurants, 20 minutes from the Football hall of fame.

Superhost

A spacious deck overlooks a tranquil river, framed by lush greenery and rolling hills. Comfortable seating is provided on the deck, inviting relaxation as the sunset casts a warm glow across the landscape.

Cottage in Parker

4.89 out of 5 average rating, 200 reviews

Riverfront Retreat–Kayak, Trails, &Foxburg Nearby

Riverfront 2 Bedroom/1 Bath cottage. Large deck and a fire pit below and large front lawn. Steps from kayaking, swimming, and fishing. 1.5 miles to the Allegheny River Trail (Rails to Trails) Trailhead, Mineral Springs Park, grocery store, public boat launch, Emlenton Brew Haus, Little It Deli, & Otto's Tavern. 2.5 mi to Foxburg Pizza, Foxburg Winery, Allegheny Grille, Divani Chocolate, Foxburg Country Club

Superhost

A cabin exterior showcases a spacious wooden porch with metal bar stools, inviting outdoor seating. The structure features a stone foundation and large windows, offering views of the surrounding hillside and Tappan Lake. A gradual walkway leads to the entrance.

Cabin in Scio

5 out of 5 average rating, 3 reviews

Grand Teton: 4-6 Person Midsize Luxury Cabin

Relax with the whole family at this beautiful cabin which is on the hillside at our Tappan Lakeside Resort located across from Tappan Lake! This cabin has a lot to offer, with a fully stocked kitchenette, a complete bathroom and all of the linens and utensils you'll ever need. Don't forget the porch complete with a gas grill and adirondack chairs. The views are breath taking!

Guest favorite

A fire pit is surrounded by six colorful Adirondack chairs on a grassy area, with a view of the lake in the background. Trees line the shore, and the water reflects a cloudy sky, creating a serene outdoor space for relaxation.

Home in Deerfield

4.92 out of 5 average rating, 163 reviews

Lakefront Paradise on Berlin Lake

The Dock is in. Here’s your self insolation destination you’ve been looking for. You will have a completely clean house right on the lake all to yourself. Wake up to a beautiful sunrise and watch the eagles soar. All of your stress will be a distant memory. You can go for walks in the nearby woods and reconnect with your self and family. You won’t be disappointed!

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What guests are saying

The Carl’s Family Cabin

4.93 out of 5 average rating, 69 reviews1 month ago

If you have family in this remote area, this is the place to stay. Easy to get to two local towns. The home is peaceful and relaxing. A Ohio girl who turned Floridian, found it very refreshing to find a quiet, clean, place with all the amenities. Wonderful home for to visit family young and old.

Cabin in Minerva

What guests are saying

Modern spacious cozy home

4.91 out of 5 average rating, 64 reviews2 weeks ago

Great house, right by all the major attractions in Pittsburgh! This was the perfect spot for us. Just an FYI, it’s in a very hilly area of Pittsburgh so there are quite a bit of steep stairs getting into the house but no problem for us. We loved the place and would recommend to others!

Home in Pittsburgh

What guests are saying

3 King Beds! Garage! Theater! Great Location!

5 out of 5 average rating, 47 reviews2 weeks ago

As advertised. Easy to find, easy to check in. The house was very very clean. We had no issues at all with anything. The location was great to all of our destinations including restaurants. The neighborhood was quiet and parking behind the house was great. I would recommend this house to anyone. It was perfect for our family of four with bedrooms and bathrooms. The beds, sheets, and pillows were comfortable. It was a great stay and would definitely stay here again if in the Pittsburgh area!

Home in Mexican War Streets

What guests are saying

Rivers Edge 2.0

5 out of 5 average rating, 47 reviews2 days ago

Carrie's place is located in a peaceful neighborhood right on the Ohio River. It is within walking distance of a small park. Restaurants and shopping are also within a short driving distance. distance. The place is well stocked, and Carrie's extras were much appreciated after a very long drive. I will definitely stay here again if I am ever back in the area. My friend and I had a much-needed relaxing weekend.

Home in Monaca

What guests are saying

Weekly discount. Pet friendly. Walk to dine/shop.

4.92 out of 5 average rating, 92 reviews1 month ago

Michelle was so responsive and easy to communicate with. Her place was very accommodating for my mom and I when we stayed during my father’s surgery and post op recovery at the hospital. This home had everything we need for our 5 day stay. We didn’t come across anything we wish we would have had. Very comfortable beds and very caring host. Thanks Michelle!

Home in Butler

What guests are saying

Cozy country home sleeps up to 9 guests

5 out of 5 average rating, 15 reviews2 days ago

Bob was great! He is responsive and friendly and easy to reach. Property is beautiful and great location to popular restaurants and the quaint college area. We came to visit family and the location was 1.5 miles from them! Overall the home was “homey” and comfortable and lovely.

Home in New Wilmington

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Stay near Chester's top sights

Sparkle Market3 locals recommend

Saddle Ridge3 locals recommend

Casa de Emanuel3 locals recommend

Other great vacation rentals in Chester

Superhost

A spacious bathroom features a double vanity with marble countertops, equipped with modern faucets. Natural light enters through a window, illuminating the neutral-toned walls and flooring. A tub and a walk-in shower are included, alongside a toilet positioned in a separate area.

Home in Sarver

4.8 out of 5 average rating, 44 reviews

Cozy Farmhouse Retreat

Top guest favorite

A modern bathroom features a spacious walk-in shower with intricate tile work and a glass enclosure. Soft lighting illuminates the room, which includes a granite countertop with a vessel sink. The space has textured walls and decorative accents, adding to its functionality.

Bungalow in Oakmont

4.97 out of 5 average rating, 58 reviews

Oakmont Bungalow with private hot tub

Guest favorite

A wooden deck is presented, featuring a spacious floor with a natural finish. Steps lead down to a grassy area surrounded by trees displaying vibrant autumn foliage, creating a serene outdoor setting.

Home in Carrollton

4.91 out of 5 average rating, 11 reviews

Oak Haven Retreat: Tranquil Stay w/King bed

Guest favorite

A spacious living room is highlighted by a comfortable sofa with decorative pillows and a wooden coffee table. Elegant windows allow natural light to brighten the space, complemented by a flat-screen TV and a decorative fireplace. A cozy armchair enhances the inviting atmosphere.

Apartment in Shadyside

4.93 out of 5 average rating, 30 reviews

Spacious 1 bd in Shadyside - Walk to CMU and Pitt

Guest favorite

An expansive common area is shown featuring a billiards table at its center. Surrounding spaces include stylish seating arrangements, built-in shelves displaying decor, and a range of windows allowing natural light to brighten the wooden floors.

Apartment in Pittsburgh

4.89 out of 5 average rating, 140 reviews

Luxury Apartment with Balcony Near Stadium

Superhost

A spacious hot tub features multiple seating areas and massaging jets, surrounded by illuminated accents. The clean water reflects the soft, ambient lighting, creating a relaxing atmosphere. The control panel and safety features are also visible, ensuring a user-friendly experience.

Home in Renfrew

4.87 out of 5 average rating, 71 reviews

Stunning 4 bedroom, female veteran owned, multi level home. perfect for a long weekend while attending any of the 4 wedding venues within 3 miles of the front door. The beautifully designed patios are perfect for hosting both outdoors and indoors!

Guest favorite