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Vacation rentals in Cheswick

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Top-rated vacation rentals in Cheswick

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Home in Monroeville

4.81 out of 5 average rating, 186 reviews

Pittsburgh Hideaway - Pets - Private

-Discounts on weekly and monthly stays - Put in dates for prices. -1 bedroom house with 1 bath and everything you need for a comfortable stay. -House is tucked away, but also close to the highway and turnpike. -Walking distance to UPMC East, 6 minutes to Forbes Hospital, and min from major shopping/restaurants. -Pet friendly with a large yard (no fence). -Dog park only 7 minutes away - Monroeville Dog Park. Boyce Park and Penn Hills (fenced dog parks) 15 min away -TV- Amazon Stick to login

Jun 11 – 18

G$21,651 GYD per night

Home in Verona

4.87 out of 5 average rating, 248 reviews

Wyckoff-Mason Log House 1774 Historic Landmark

Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

Apr 23 – 30

G$21,686 GYD per night

Guest suite in Pittsburgh

4.94 out of 5 average rating, 235 reviews

Warm & Cozy, Newly Remodeled Private Space.

The PITT Stop Explore Pittsburgh’s vibrant streets with this warm & cozy, newly remodeled studio as your base! The PITT Stop is centrally located in Brighton Heights, a smaller section of Pittsburgh’s North Side. One of the most historic and culturally eclectic areas you will find. Here in Brighton Heights, you’ll be rooted in the coziness of an urban neighborhood while being close to everything metropolitan Pittsburgh has to offer. **Please see ‘Other Details to Note’ section for more.**

Mar 7 – 14

G$20,384 GYD per night

Guest suite in Pittsburgh

4.97 out of 5 average rating, 140 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Oct 13 – 20

G$16,500 GYD per night

Apartment in Valencia

5.0 out of 5 average rating, 115 reviews

Inspired farmhouse apartment

Enjoy the ambiance of this calm, stylish farmhouse, enhanced by an abundance of natural light. Every detail is fresh, new & carefully designed for your comfort (including queen bed with new, high-quality Serta mattress & luxury pillows, beautiful & spacious tub/shower, restored hardwood floors, 3/4 sized stove & frig, Keurig & more). And outside? Real farm life views! Great bistro/restaurants nearby. Quick access to main roads take you to Cranberry Twp. (8 mi.), Downtown Pittsburgh (15 mi.).

Feb 17 – 24

G$25,821 GYD per night

Apartment in Pittsburgh

4.95 out of 5 average rating, 388 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Sep 25 – Oct 2

G$19,212 GYD per night

Guest suite in West Mifflin

4.99 out of 5 average rating, 104 reviews

Hilltop Suite, Quiet Street

My wife Steph and myself (Chris) would like to welcome you to our guest suite. We think that you will find our small suite very cozy and will find everything that you need. You will have your own entrance through the back of the house as well as onsite parking. Inside, we've worked hard to make the space very updated and clean. Amenities include your own bathroom with a deluxe shower, an in-suite mini kitchen with stove and fridge, a small dining table, a couch, and a comfy queen bed.

Aug 20 – 27

G$23,193 GYD per night

Guest suite in Gibsonia

4.94 out of 5 average rating, 141 reviews

Cozy Comfortable Retreat #1

Beautiful basement guest suite with a gas fireplace, full bath, kitchen with cooktop stove, mini refrigerator and microwave/convection oven. Enjoy off street parking in a quiet friendly neighborhood with outdoor patio. Close to shopping, restaurants, North Park and Hartwood Acres. Downtown Pittsburgh is less than 13 miles away which allows for easy access to all the sporting events Steeler games, Pirate games and Penguin games. Located less than 2 miles from the PA turnpike exit.

Aug 4 – 11

G$20,037 GYD per night

Apartment in Pittsburgh

4.91 out of 5 average rating, 328 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

Oct 28 – Nov 4

G$19,713 GYD per night

Cabin in Pittsburgh

4.92 out of 5 average rating, 127 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost/night is $135.00 for 2 adults. Extra adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day.

Feb 5 – 12

G$32,203 GYD per night

Apartment in Pittsburgh

4.99 out of 5 average rating, 145 reviews

504 Bascom Ave Serene Luxury

Nestled in the middle of an adorable community of stone cottages, this historic structure built in 1938 was the first home John Mattys built in this neighborhood. He went on to build all the houses on Mattys (named after himself) and Oceanas Avenues (named for the sisters that commissioned and lived in this duplex). Re-imagined for contemporary lifestyles, 504 Bascom is your cozy cottage but with all the amenities you deserve. I look forward to hosting you!

Oct 3 – 10

G$24,341 GYD per night

Apartment in Glenshaw

4.95 out of 5 average rating, 197 reviews

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

Sep 21 – 28

G$16,305 GYD per night

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Popular amenities for Cheswick vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Cheswick

Apartment in East McKeesport

4.95 out of 5 average rating, 259 reviews

Quiet Luxury Apartment!

Oct 11 – 18

G$28,006 GYD per night

Apartment in Springdale

4.79 out of 5 average rating, 42 reviews

2br gem in cute small town.

Sep 16 – 23

G$20,509 GYD per night

Home in Monroeville

5.0 out of 5 average rating, 14 reviews

Monroeville 2 bedroom 2 queen size beds

Dec 23 – 30

G$20,862 GYD per night

Guest suite in Oakmont

4.8 out of 5 average rating, 89 reviews

Cozy one bedroom suite

Nov 24 – Dec 1

G$29,825 GYD per night

Home in New Kensington

4.98 out of 5 average rating, 66 reviews

Mid-Century Burrell Bungalow

Sep 9 – 16

G$38,329 GYD per night

Guest suite in Sarver

5.0 out of 5 average rating, 20 reviews

Open concept design studio

Sep 11 – 18

G$25,999 GYD per night

Home in Pittsburgh

5.0 out of 5 average rating, 11 reviews

Cozy three bedroom home close to shopping and more

Jun 14 – 21

G$31,493 GYD per night

Guesthouse in Oakmont

4.97 out of 5 average rating, 76 reviews

Cozy Carriage House in Oakmont, PA

Jul 19 – 26

G$37,269 GYD per night

Destinations to explore