Vacation rentals in Chestnut Ridge

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chestnut Ridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Brownsville

4.91 out of 5 average rating, 82 reviews

Maria's Lovers House in Historic Brownsville, PA

Travel back to the 1940's and experience the period in a historical river town in Western, PA. This fully restored house was a primary film location for Maria's Lovers, a post WWII period film (released in 1984). The parlor, dining room, kitchen, porches, and bedrooms are completely decorated in fine antiques and movie memorabilia. Also enjoy spectacular views of the river, brand new bathrooms, utilities, WiFi, quality Purple mattresses and linens, and all the Brownsville's historic venues.

Guest favorite

An elevated deck features wooden railings and a smooth wooden floor, providing a spacious area with table and chairs for outdoor relaxation. Lush greenery surrounds the deck, enhancing the natural atmosphere. Vibrant flowers are seen at the edge, adding subtle colour to the setting.

Home in Perryopolis

4.84 out of 5 average rating, 281 reviews

132 Wickhaven-Deer Path Lane Guesthouse

If you enjoy privacy and pretty scenery this is the place for you. Enjoy nature and the sounds of waterfalls from the elevated deck. This two bedroom house is all by itself with an updated kitchen. Just a short drive to Laurel Caverns, Falling Water and Ohiopyle. There is plenty of firewood on site for campfires. The long driveway is dirt and gravel and rough and you have to ford a small stream. You don’t need a 4 wheel drive but you do need a vehicle with clearance. Pickup or SUV recommended.

Top guest favorite

A modern architectural gem is set amidst lush greenery, featuring large windows that reflect the surrounding landscape. A serene waterfall flows beneath the structure, enhancing the natural beauty of the environment, while the stone and concrete exterior harmonizes with the rustic terrain.

Home in Connellsville

4.97 out of 5 average rating, 157 reviews

Vintage Vogue Suite with Wi-Fi+Netflix/Parking

Stay in our elegant Vintage-Modern Home Only 20min from Fallingwater. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dining and fully stocked Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Washer/dryer ✔Free breakfast Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Top guest favorite

A black front door features a modern design with multiple rectangular glass panels. A welcome mat is placed on the entrance, set against a backdrop of horizontal brown siding and a wall-mounted light fixture.

Apartment in Perryopolis

4.99 out of 5 average rating, 139 reviews

Relaxing River View Apt near MM103 of GAP trail

Enjoy a river view escape with direct access to the Greater Allegheny Passage (GAP) Bicycle Trail, and the Youghiogheny River in the quaint town of Perryopolis, PA, just 31 miles south of Pittsburgh. All new modern apartment. Bike 50 miles into, or from, Pittsburgh with stops along the way to shop and eat. Very close to both Winslow and Visnoski Wineries which often have outdoor music and concerts! Or spend the afternoon, relaxing on the deck. Restaurants and groceries available in town.

Top guest favorite

An open interior space showcases rich wooden walls and a vaulted ceiling with warm lighting. A dining table, set for meals, is positioned near a window. The kitchen area is visible, equipped with modern appliances, and the entrance features a rustic wooden door.

Cottage in Mount Pleasant

5 out of 5 average rating, 214 reviews

Sunbeams Cottage

Small home is completely remodeled using traditional woodwork craftsmanship for a warm feel. Full appliances and amenities are supplied in the cottage. Evening and breakfast snacks included. Tasty public tap water for drinking and cooking. Private lane leads to the home with a spacious covered porch overlooking hillside and field. Ideal location at foothills of Laurel Highlands and outskirts of Pittsburgh. Town of Mt. Pleasant is just minutes away providing restaurants and shopping.

Guest favorite

The aframe cabin is nestled among dense trees, with a wooden deck extending out front. Two white Adirondack chairs are positioned on the deck, providing a serene view of the surrounding forest.

Cabin in Mineral County

4.96 out of 5 average rating, 144 reviews

Glamping in a Creekside Aframe

This cozy aframe is a perfect glamping getaway for two! You'll stay on 20 acres with over 700 feet of frontage on Abrams Creek. Ready to unplug? The aframe is completely off grid with solar energy and a wood-fired stove. Sleep in luxury with fine linens and a queen size bed, but spend your day splashing in the crystal clear creek and hiking through the forest. Enjoy your evening playing cornhole while dinner cooks on the grill, topped off with a favorite beverage around the campfire.

Top guest favorite

The Hobbit House features a unique multi-level design with a grassy roof and vibrant red doors. A pathway leads to the front, flanked by lush greenery and stone accents, while a decorative wheel is positioned near the entrance, adding to the charming exterior.

Cabin in Farmington

4.99 out of 5 average rating, 160 reviews

Ohiopyle Hobbit House

One of a kind Lord of The Rings themed Hobbit House. With hidden surprises around every turn. You won't be able to stop uncovering the small details that will add to your enjoyment of your stay. Almost everything in the house was custom made by the builder to add to the unique charm of the house. From the medieval doors with operable speak easy look throughs and the whiskey barrel cabinets, you don't want to miss putting this house on your travel bucket list.

Guest favorite

The living area features a comfortable couch and armchair set near a stone fireplace. Large windows allow natural light to fill the space, offering views of surrounding greenery. A dining table is positioned nearby beneath exposed beams and a ceiling fan.

Chalet in Acme

4.94 out of 5 average rating, 262 reviews

Secluded Chalet near Ohiopyle and Seven Springs

Leave the bustle behind for the whispering oaks and calming embrace of our renovated Laurel Highlands chalet. Enjoy grilling on the deck, sitting around the fire ring, watching wildlife in the woods, or reconnecting with friends and family inside the cozy chalet. Shrouded by towering oak trees, the chalet is quiet and feels secluded. Yet, it’s only minutes away from Ohiopyle, Seven Springs, Fallingwater, and other popular attractions in the Laurel Highlands.

Top guest favorite

A comfortable porch area is visible, featuring a small round table with two chairs. A hanging basket filled with purple flowers is showcased, while a well-maintained grassy lawn and trees provide a serene backdrop. Nearby homes can be seen in the distance.

Apartment in Monongahela

5 out of 5 average rating, 30 reviews

Charming Loft in Historic Town

This is a newly renovated loft apartment above the garage in a quiet older established neighborhood with treelined streets and beautiful well kept historic homes in Monongahela, PA. Close access to Routes 43, 70, 51 and interstate 79. This rental provides access to the greater Pittsburgh area and the larger cities of Uniontown, Greensburg and Washington areas. All of these areas are within 25 miles of the property.

Guest favorite

A modern living space showcases a sleek fireplace set within a stone surround, complemented by a flat-screen television mounted on the wall. A desk with a stylish chair is positioned next to a mirror, near a kitchenette that includes a microwave and a refrigerator.

Apartment in Coal Center

5 out of 5 average rating, 35 reviews

Riverview Suites

Discover the serene charm of our private riverfront rooms, thoughtfully nestled near the picturesque Pennwest University. Our “One Bedroom Luxe Suite” offers a unique blend of comfort and convenience. Private off street parking and gated privacy for your relaxation. Embrace nature as you gaze upon the mesmerizing river views from our expansive connecting deck and inviting gazebo.

Top guest favorite

Treehouse in Swanton

4.99 out of 5 average rating, 204 reviews

The Overlook; A Romantic Treehouse for Two

The Overlook welcomes you with stunning views of the Appalachian Mounains and offers luxurious first class amenities! * Mountain Views * Private Deck * Hot tub * Outdoor Tv * Gas Fire Pit * Large two person egg chair * Soaking Bathtub * Luxury tile shower * Full Kitchen * King Bed * Wifi * 100 inch Movie Projector screen * Bluetooth Mantle Soundbar

Guest favorite

A serene lakeside area is framed by lush greenery. Two black chairs circle a fire pit made of stone, with firewood stacked nearby. A wooden platform extends over the water, offering a peaceful spot to relax and enjoy nature.

Shipping container in Acme

4.9 out of 5 average rating, 219 reviews

The Laurel Haven Container

Experience the soothing sounds of nature during your stay in the laurel haven container. Designed for relaxation and reconnecting with the outdoors, this lakeside retreat offers a peaceful escape like no other. Nestled in the heart of Pennsylvania’s Laurel Highlands, it’s the only container home of its kind in the region!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chestnut Ridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chestnut Ridge

A coffee maker sits on a countertop beside a travel mug and a stack of foam cups. A drawer is open, revealing several coffee pods organized neatly. The surface is topped with a light-colored countertop, contributing to a functional kitchen space.

Home in West Newton

4.82 out of 5 average rating, 17 reviews

Railside Inn

JasonRating, 5 stars5 days ago

Convenient location in West Newton. Host communicated well.

Top guest favorite

An outdoor dining area is presented with several tables and chairs under shaded umbrellas. The rustic structure features a wooden exterior and is surrounded by green grass, with rolling hills visible in the background.

Private room in Smithton

4.96 out of 5 average rating, 140 reviews

*Clubhouse* Van Meter right next to GAP Trail!

EllieRating, 5 stars3 weeks ago

Julia’s unit is right on the GAP bike trail, making it a perfect stop for bikers on multi-day trips. It’s located between Mileposts 106 and 107 on the GAP trail. The beds were comfortable, and there are snacks for purchase on the patio. We had a very relaxing stay.

Guest favorite

A wall features a vintage black-and-white photograph of a baseball player in a crouched position, accompanied by a tabletop displaying an extensive collection of baseball cards. A calendar, commemorative plaque, and a team jersey hang nearby, contributing to a sports-themed decor.

Home in Connellsville

4.88 out of 5 average rating, 8 reviews

The Baseball House

AllieRating, 5 stars3 days ago

I brought my children with me on my work trip and this place was fabulous for my family. Highly recommend for any family. Lots of things to do for the kids and it was private and peaceful. Great host!

Guest favorite

The kitchen features a central island with four bar stools and an adjacent countertop showcasing modern appliances, including a refrigerator and coffee maker. Light-colored cabinetry contrasts with the dark granite surfaces. A decorative display cabinet is positioned against the wall, enhancing storage and functionality.

Cabin in Greensboro

4.8 out of 5 average rating, 5 reviews

Country Cabin Getaway

SharonRating, 5 stars1 week ago

Marks home was exactly as shown in the pictures. The kitchen had everything we needed to prepare our meals and the beds were awesome. Mark quickly responded you all our needs and was great to work with. We’d book again if we’re back in the area.

A compact kitchen area with modern grey cabinetry and white appliances is visible. A dining table, covered with a black and white checkered tablecloth, is set for two. Ample lighting enhances the functional workspace, and details such as a fire extinguisher are also present.

Apartment in Uniontown

4.84 out of 5 average rating, 43 reviews

Cozy ground level apartment!

AngelineRating, 5 stars1 week ago

Misty's home was close to the church we were going to for a memorial service & close to downtown & library - great for our visit - nice kitchen & new flooring throughout - excellent communication & friendly clean team / they agreed to mail a computer charger we left behind - much appreciated

Guest favorite

A small bathroom is visible through an open door, featuring a white shower curtain drawn over a shower. A toilet is positioned next to a basin with a dark countertop. A striped rug lies on the floor, complementing the neutral color scheme of the space.

Home in Uniontown

5 out of 5 average rating, 9 reviews

Cozy 3bd, 2bath for family vacation/hiking/getaway

DannielleRating, 5 stars3 days ago

Carley is a wonderful host. Always takes care of anything and any request within a timely fashion.

Guest favorite

A red wooden fence outlines a green grassy area, providing a boundary for the yard. A solitary chair sits nearby, shaded by overhanging branches. The background displays a rolling landscape, featuring trees and a hint of the peaceful neighborhood.

Home in Luzerne Township

4.86 out of 5 average rating, 43 reviews

Quiet Space with Spacious Yard in Nice Community

JasonRating, 5 stars3 months ago

Tamika responded and addressed all of my questions very quickly. We loved the location and the house. It's so quiet at night so we slept great. We saw 2 turkeys and multiple deer during our stay. Do yourself a favor and grab a few peperoni rolls at the Penncraft Market at the end of the street. I would recommend staying here. If I end upI working in the are again, we will be back.

Top guest favorite

The bathroom features a modern vanity with dual drawers and a granite countertop, complemented by a round mirror. Neutral tile work adorns the wall, while a toilet is positioned nearby, creating a functional and tidy space.

Private room in Hopwood

4.96 out of 5 average rating, 304 reviews

Comfortable room for 2 in country

DarlaRating, 5 stars9 months ago

This was a perfect stay for us! Keith was a generous and responsive host who immediately made us feel right at home. The space was super clean and location convenient for our evening event. Keith greeted us in person and we especially enjoyed the delicious breakfast and friendly conversation in the morning. Easy parking, clear and detailed messages, and the kindness of Keith contributed to a wonderful memory. HIGHLY RECOMMEND!!

Show all

Vacation rentals in Chestnut Ridge

Top-rated vacation rentals in Chestnut Ridge

Vacation rentals for every style

Popular amenities for Chestnut Ridge vacation rentals

Other great vacation rentals in Chestnut Ridge

Destinations to explore