Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

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

0 of 0 items showing

1 of 3 pages

Superhost

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

4.78 out of 5 average rating, 9 reviews

Secluded cabin on the lake shore - Sm Dogs Allowed

BarbaraRating, 5 stars7 months ago

Marissa's cabin was exactly as promised! This was are 4th year of coming to Leesville Lake to fish. The fishing this year was not the best and I'm pretty sure the drought is over, can't control the weather. Staying at the cabin was a total pleasure, the enclosed porch area is very comfortable and a great place to spend a rainy day! We were able to enjoy a outside fire on our first night, and totally enjoy the night time calming sounds of the lake, the owl every evening was a plus. When we were unable to spend our evening outside around the fire ring the fireplace in the living room was a great replacement, there is nothing like a fire and watching a movie to relax. It was very nice not having TV and all the political commercials. If you are looking for a beautiful place to get away and relax this is the place.

Top guest favorite

A modern three-story home is shown, featuring large glass windows that allow ample natural light. The exterior showcases a combination of sleek metal siding and neutral tones, with a driveway leading up to the garage. Two neighboring buildings are visible on the right.

Home in Mexican War Streets

5 out of 5 average rating, 48 reviews

3 King Beds! Garage! Theater! Great Location!

NiamhRating, 5 stars1 week ago

This was our first Airbnb experience — we usually stay in hotels — and we’re officially converted! The house was exactly as described: very clean, well-equipped, and perfect for our stay. We especially loved having the extra space for our kids. The location was fantastic, within walking distance to parks, coffee shops, and museums. Our host was incredibly responsive and helpful throughout. One thing to note if you're traveling with kids: the third bedroom is on the ground/first floor, while the other two bedrooms are on the third floor.

Top guest favorite

Cottage in Mercer

4.98 out of 5 average rating, 62 reviews

Mermaid Inn romantic house on the lake

Leigh AnnRating, 5 stars6 months ago

Anna thought of everything someone might need for a “home away from home.” The place was beautifully decorated with everything seemingly brand new. It was a very comfortable and peaceful place to hang out. Being outside was so relaxing. We enjoyed the pond and the backdrop of woods with changing autumn leaves. It was the perfect location being so close to the outlets and restaurants too.

Top guest favorite

Home in New Wilmington

5 out of 5 average rating, 15 reviews

Cozy country home sleeps up to 9 guests

JessicaRating, 5 stars1 week 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.

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, 4 reviews

Grand Teton: 4-6 Person Midsize Luxury Cabin

AshleyRating, 5 stars6 months ago

We had a great trip and are already looking forward to coming back. The cabin was relaxing and the views were beautiful. They offer Kayaks rentals which we plan to try out next time when it’s warmer. Plus The store is conveniently located when you need something. A great overall experience.

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 Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Guest favorite

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

5 out of 5 average rating, 8 reviews

Spacious home with great views

JasonRating, 5 stars2 days ago

wonderful place to stay, and very homie. host was excellent, all and all ah wonder stay

Guest favorite

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

4.89 out of 5 average rating, 82 reviews

Cozy Relaxing Home

CarolynnRating, 5 stars2 months ago

Super clean place! That’s what I care most about when traveling. The kitchen had everything we needed. We had to extend our stay and the host made it super easy to do. Washer and dryer is a must for us with a 4 year old. Thank you for everything!

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

LisaRating, 5 stars7 months ago

We had a great stay at Laura’s place. The bungalo was adorable & comfortable. It had everything we needed. We felt right at home. It was very clean. Location was great! Couldn’t beat being down the block from Oakmont Bakery. There is a park right across that our Grandson had fun at. Quiet neighborhood. Laura was a great host. Highly recommend.

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

ErinRating, 5 stars2 weeks ago

Had a great stay at Christine’s!! Beautiful surroundings, big beautiful space in the apartment, and everything was so CLEAN! Nice and relaxing getaway, and I highly recommend!

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

AideenRating, 5 stars10 months ago

We really enjoyed staying at Grace's place as it was spacious and comfortable. It's beautifully decorated and has period features and charm. In spite of early traffic we slept soundly in a very comfortable bed. The water was always hot and the shower powerful,the separate sinks was a novelty! It was great to be able to was our clothes too... We loved Shadyside too as it was a beautiful,peaceful neighbourhood with lots of good restaurants and bars which Grace recommended. The bus stops down the street and the 71B takes you to town near where the three rivers meet. Take the hop-on,hop-off tour and see the city. We got the 28x to the airport for $2.75,for nothing! Overall we would highly recommend Grace's place,Shadyside and Pittsburgh.

Guest favorite

The spacious kitchen features a central island with a seating area, modern appliances, and stylish cabinetry. Natural light enters through large windows, illuminating the comfortable living area that includes a sectional couch and a decorative rug, creating a welcoming ambiance.

Apartment in Pittsburgh

4.89 out of 5 average rating, 141 reviews

Luxury Apartment with Balcony Near Stadium

NicoleRating, 5 stars1 week ago

We had a great stay for a weekend trip. Ideal location to walk to PNC park. The space was clean and had the amenities that were needed for a short trip. The building was very nice and parking was easy. Great spot to get to different areas in Pitt.

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!

RosemaryRating, 5 stars2 months ago

This was a great venue for our cozy and quiet bachelorette party! There was plenty to do nearby and we loved using the hot tub in the cold weather! Thank you for a wonderful stay!

Guest favorite