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15 Aug - 17 Aug
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5 Sept - 7 Sept
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Browse Select North Side Cottages

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
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
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Enjoy al fresco dining with a grill and comfortable seating.

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

9.6 out of 10, Exceptional, (148)
"The cottage is very whimsical and cozy. The view was amazing night and day. We enjoyed the fireplace and the French pastry shoppe La Gourmandine. We would rent this place again. "
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
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!
Relax on the covered porch with a view of the surrounding neighborhood.

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!
Stroll through a charming neighborhood with well-manicured lawns and a variety of homes, including a two-story house with a front porch and garage.

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!
Staircase leads to a charming building with a naturalistic setting, surrounded by plants and rocks.

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!
Rows of two-story homes with gabled roofs line the street.

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
Relax on the covered porch with a view of the street, featuring a wicker chair and large windows.

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!
Stroll up to this charming two-story home with a welcoming front door and cozy porch area.

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!
Two-story house with a white picket fence and a well-maintained lawn.

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!
Stylish building with a flat roof and balconies, set amidst a beautifully maintained front yard with a gravel pathway and lush shrubs.

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!
Deck & Patio: Inviting Abode in Natrona Heights!
House (2 Bedrooms) | Front of property

Deck & Patio: Inviting Abode in Natrona Heights!

3.0 star property
8.0 out of 10, Very good, (1)
"Pleasantly surprised. It’s a nice, quiet and clean homey spot but there is nothing to do in the surrounding area."
Deck & Patio: Inviting Abode in Natrona Heights!
Romantic Cottage In The Village Of Sewickley
Relax in a well-read environment with a comfortable sofa, wooden coffee table, and a patterned rug.

Romantic Cottage In The Village Of Sewickley

Romantic Cottage In The Village Of Sewickley
Monroeville Vacation Rental - 2 Mi to Downtown!
Enter a cozy home with a small front porch and steps leading up to the entrance.

Monroeville Vacation Rental - 2 Mi to Downtown!

3.0 star property
Monroeville Vacation Rental - 2 Mi to Downtown!
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
Family-friendly Shadyside Gem Near Dtwn Pittsburgh
Stylish two-story home with a front porch, outdoor seating area, and garage.

Family-friendly Shadyside Gem Near Dtwn Pittsburgh

3.0 star property
Family-friendly Shadyside Gem Near Dtwn Pittsburgh
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 North Side Hotel Reviews

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

10/10 Excellent
"Hotel staff was great, property was beautiful "
Saliena 2-night trip
Posted 20 hours ago
Kimpton Hotel Monaco Pittsburgh by IHG