Vacation rentals in Chester

4.78 out of 5 average rating, 9 reviews

The exterior of the chalet showcases a combination of dark wood and stone elements, framed by green landscaping. A large porch extends across the front, offering outdoor seating. Surrounding trees provide natural shade, and a stone pathway leads to the structure.

Home in Carrollton

Secluded cabin on the lake shore - Sm Dogs Allowed

A remodeled chalet nestled away in Leesville's wilderness. This cabin comes with great views from either of its three porches. It’s driving distance away from family-friendly events like the Algonquin Mill Festival. It features a full kitchen with cooking items and a Keurig, blender, toaster, etc. This area is a perfect getaway. The lake has a 10HP limit for boats and is a perfect fishing and kayaking lake. It is across the street from a natural walking trail. Cell service can be spotty. No WIFI

4.89 out of 5 average rating, 153 reviews

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

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!

Home in Mexican War Streets

A spacious living room is furnished with a large, comfortable couch adorned with assorted cushions. A sleek projector screen is mounted on the wall, while a stylish area rug adds warmth to the hardwood floor. A dining area is visible in the background, enhancing the open layout.

5 out of 5 average rating, 51 reviews

3 King Beds! Garage! Theater! Great Location!

Perfect for families & traveling groups of friends, our new construction home is ready for its first guests! All three bedrooms have king beds along with a private attached bathroom, perfect for travelers wanting privacy. No need to search for parking, with garage + driveway parking for 2 vehicles. Create a memorable meal in our well stocked kitchen, relax on the couch and watch the 120" screen, or take a short stroll to the numerous bars & restaurants in the area. You can't beat this location!

4.9 out of 5 average rating, 272 reviews

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

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..

4.82 out of 5 average rating, 89 reviews

Two white wooden chairs with a glass table are positioned on a covered deck. The railing offers a view of the lake, with trees visible in the background and a sandy area nearby. Clear skies are present, enhancing the calm atmosphere.

Home in Lake Milton

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).

5 out of 5 average rating, 12 reviews

Home in Columbiana

Charming Home Walking Distance to Main Street!

Welcome to Your Home Away From Home! Experience relaxed country living in our newly renovated haven. Walk to local attractions like Birdfish Brewing, Generations Café, R’s Pizza Place, and Hogan’s Baking. Explore Main Street for unique shops and restaurants. Enjoy outdoor activities at Firestone Park with its pool, courts, and more. Conveniently just a 2-minute drive to Route 11. Enjoy the perfect blend of tranquility and convenience. Book your stay today!

4.98 out of 5 average rating, 63 reviews

Cottage in Mercer

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

4.91 out of 5 average rating, 67 reviews

Home in Pittsburgh

Modern Spacious Cozy Home Near Southside

Welcome to your clean, comfortable home away from home! This 4-bedroom, 1.5-bathroom house offers the perfect blend of modern design and cozy charm—ideal for families, groups, or anyone looking to explore Pittsburgh with ease. Located in a friendly neighborhood with quick access to downtown, parks, and local attractions, this home is your perfect Pittsburgh landing spot—peaceful, polished, and ready for your stay.

4.9 out of 5 average rating, 183 reviews

A wooden deck is framed by lush greenery, providing a glimpse of a tranquil river beyond. Sunlight reflects off the water, adding a serene quality to the natural setting.

Home in Alliance

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.

5 out of 5 average rating, 16 reviews

Home in New Wilmington

Cozy country home sleeps up to 9 guests

Fully renovated home. Sleeps up to 9. Luxury bedding and appointments, full kitchen. Basement has separate television and couch as well as ping pong and foosball tables. Perfect for couples' getaway, weddings, funerals, college parent days and fishermen plying our amazing area trout streams. Close to Hermitage, New Castle, Butler and Youngstown. One hour to Pittsburgh and 1:30 to Cleveland, Akron and Erie.

5 out of 5 average rating, 5 reviews

A cabin is nestled on a hillside surrounded by autumn foliage, showcasing vibrant leaves in shades of orange and yellow. Steps lead up to the cabin, which features a welcoming wooden porch and an inviting entrance. A parking sign is visible at the base of the steps.

Cabin in Scio

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!

4.92 out of 5 average rating, 164 reviews

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

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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Other great vacation rentals in Chester

5 out of 5 average rating, 9 reviews

The image captures a panoramic view of the city skyline at sunset, with colors transitioning in the sky. A wooden deck, adorned with string lights, extends over the scene, while lush greenery frames the foreground, providing a contrasting natural element to the urban landscape.

Home in South Side Flats

Spacious home with great views

4.89 out of 5 average rating, 82 reviews

A modern kitchen is shown with sleek white cabinetry and stainless steel appliances. A wooden island stands at the center, surrounded by stylish dining chairs. Natural light enters from a nearby window, enhancing the contemporary design and functionality of the space.

Home in Youngstown

Cozy Relaxing Home

4.97 out of 5 average rating, 60 reviews

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

Oakmont Bungalow with private hot tub

4.92 out of 5 average rating, 13 reviews

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

Oak Haven Retreat: Tranquil Stay w/King bed

4.93 out of 5 average rating, 30 reviews

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

Spacious 1 bd in Shadyside - Walk to CMU and Pitt

4.9 out of 5 average rating, 144 reviews

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

Luxury Apartment with Balcony Near Stadium

4.88 out of 5 average rating, 73 reviews

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

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!