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22 Aug - 24 Aug
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29 Aug - 31 Aug
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12 Sept - 14 Sept
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Featured Cottages in South Side

Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Outdoor dining

Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet

9.6 out of 10, Exceptional, (148)
"This is a sweet cozy cottage hidden among the trees with beautiful flowering bushes. We came days after a severe storm blew through Pittsburgh and unfortunately power outages everywhere. The host Laura was extremely helpful throughout our stay. We enjoyed watching the birds on the back deck and grilling dinner together. "
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn
House (3 Bedrooms) | Interior

Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

3.0 star property
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn
Cozy & Comfy Cottage in the City - w/ parking!
Exterior

Cozy & Comfy Cottage in the City - w/ parking!

8.4 out of 10, Very good, (7)
"The place was perfect for friend and I who were visiting Pittsburgh to watch the NCAA basketball tournament at PPG arena. Walking distance to restaurants but it is hilly. 8min uber to PPG arena. I really is like a cottage in the city… was pleasantly surprised to see a few Deer in the back yard every morning."
Cozy & Comfy Cottage in the City - w/ parking!
3 Mi to Frick Park: Artsy, Urban Retreat w/ Deck
House (2 Bedrooms) | Interior

3 Mi to Frick Park: Artsy, Urban Retreat w/ Deck

3.0 star property
3 Mi to Frick Park: Artsy, Urban Retreat w/ Deck
Rustic Chic Retreat: 4 Mi to Kennywood!
House (2 Bedrooms) | Interior

Rustic Chic Retreat: 4 Mi to Kennywood!

3.0 star property
Rustic Chic Retreat: 4 Mi to Kennywood!
Spacious Pittsburgh Rental: Walk to Frick Park!
House (3 Bedrooms) | Interior

Spacious Pittsburgh Rental: Walk to Frick Park!

3.0 star property
Spacious Pittsburgh Rental: Walk to Frick Park!
Charming West Mifflin House - 3 Mi to Kennywood!
Interior

Charming West Mifflin House - 3 Mi to Kennywood!

3.0 star property
Charming West Mifflin House - 3 Mi to Kennywood!
Walk to Walnut St: Shadyside House w/ Deck
Apartment (2 Bedrooms) | Interior

Walk to Walnut St: Shadyside House w/ Deck

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location. Very clean. Worked perfectly for our group of 5 and dog. will definitely be returning,"
Walk to Walnut St: Shadyside House w/ Deck
Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!
Interior

Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!

3.0 star property
Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!
Charming Pittsburgh Home - Walk to Riverfront!
House (3 Bedrooms) | Interior

Charming Pittsburgh Home - Walk to Riverfront!

3.0 star property
Charming Pittsburgh Home - Walk to Riverfront!
5 Mi to North Shore: Updated Home w/ Fire Pit!
House (3 Bedrooms) | Interior

5 Mi to North Shore: Updated Home w/ Fire Pit!

3.0 star property
5 Mi to North Shore: Updated Home w/ Fire Pit!
Walk to Walnut St: Pet-friendly Pittsburgh Home!
House (2 Bedrooms) | Interior

Walk to Walnut St: Pet-friendly Pittsburgh Home!

3.0 star property
9.0 out of 10, Wonderful, (2)
"I wasn’t thrilled the rental was on a second floor when I had my dogs. Pets, unfortunately, tend to move freely and I thought the guests on the first floor below us may have been annoyed with that. I also didn’t like having to haul our luggage up many stairs, including heavy video equipment I brought with me for this scheduled trip to attend an event. I also received many emails and text messages reminding me about the trip; and overlooked that the instructions said our entrance was in the...
Walk to Walnut St: Pet-friendly Pittsburgh Home!
Modern Pittsburgh Home w/ Rooftop Deck & Backyard
Interior

Modern Pittsburgh Home w/ Rooftop Deck & Backyard

3.0 star property
Modern Pittsburgh Home w/ Rooftop Deck & Backyard
12 Mi to Dtwn: Pittsburgh Home w/ In-unit Laundry!
Interior

12 Mi to Dtwn: Pittsburgh Home w/ In-unit Laundry!

3.0 star property
2.0 out of 10, (1)
12 Mi to Dtwn: Pittsburgh Home w/ In-unit Laundry!
Game Room & Fire Pit: West Mifflin Home!
Interior

Game Room & Fire Pit: West Mifflin Home!

3.0 star property
10.0 out of 10, Exceptional, (3)
"We had a really good time staying here- we enjoyed the game room and the firepit and the rooms were quite comfortable "
Game Room & Fire Pit: West Mifflin Home!
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
House (3 Bedrooms) | Interior

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice, well kept and easy to communicate with host/ owners. Would recommend! "
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
Romantic Cottage In The Village Of Sewickley
TV, printers

Romantic Cottage In The Village Of Sewickley

Romantic Cottage In The Village Of Sewickley
Charming Vacation Rental: 15 Mi to Pittsburgh
Interior

Charming Vacation Rental: 15 Mi to Pittsburgh

3.0 star property
Charming Vacation Rental: 15 Mi to Pittsburgh
Cute Home w/ Patio ~ 7 Mi to Dtwn Pittsburgh
House (3 Bedrooms) | Interior

Cute Home w/ Patio ~ 7 Mi to Dtwn Pittsburgh

3.0 star property
4.0 out of 10, (1)
"Motion detector lights were very bright and non sense Hard mattress House older and dated"
Cute Home w/ Patio ~ 7 Mi to Dtwn Pittsburgh
Monroeville Vacation Rental - 2 Mi to Downtown!
Exterior

Monroeville Vacation Rental - 2 Mi to Downtown!

3.0 star property
Monroeville Vacation Rental - 2 Mi to Downtown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"The bed was very comfortable! Breakfast was great ,nice selection of hot foods and drinks for dinner it would be nice if they had mac@cheese and chicken instead of hot dog. We had a very enjoyable stay we will be back again next year for a ballgame"
Robert 1-night trip
Posted 12 hours ago
Drury Plaza Hotel Pittsburgh Downtown