Holiday rentals in Chester

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!

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.

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..

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.

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).

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!

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.

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!

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!