Montgomery Cottages - Vacation Rentals in Squirrel Hill

Friendship~Queen Bed ~Parking~Quiet~Central Location~Desk~Pets From US $147
         

9.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Charming 3 Bedroom Cottage Apartment in a Tudor-Style Home From US $168
         

Friendship~Queen Bed ~Parking~Quiet From US $165
         

New
Cottage
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly

Luxury Places to Stay in Squirrel Hill

Over 1315+ Luxury Places to Stay in or Near Squirrel Hill
Sleeps 36 8bd/8ba 7 sofa beds. Big enough! From US $2,159
         

2 Homes Side By Side! Sleeps 16! From US $1,362
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Entire House-City life, bring your pup! From US $1,177
         

Luxury Condo Near Shady side Hospital | King Bed From US $1,054
         

Top-Rated Vacation Rentals with a Pool in Squirrel Hill

Over 69+ Top-Rated Vacation Rentals with a Pool in or Near Squirrel Hill
PBR - Pittsburgh Bloomfield Rowhouse From US $200
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
CozySuites l Spacious SDO, Lawrenceville From US $168
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Stunning & Newest 100+ year old Historic Victorian From US $480
         

9.4 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
CozySuites Modern 1BR, Lawrenceville From US $187
         

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9.4 (6 Reviews)
Apartment
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  • Parking
  • Pet Friendly
CozySuites Trendy SDO, Lawrenceville From US $124
         

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9.3 (11 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Residence Inn Pittsburgh Oakland/University Place From US $139
         

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9.2 (917 Reviews)
Hotel
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  • Parking
  • Pool
Hyatt House Pittsburgh/Bloomfield/Shadyside From US $162
         

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9.0 (1018 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Squirrel Hill

Over 449+ Pet-Friendly Vacation Rentals in or Near Squirrel Hill
Walk to Walnut St: Pet-Friendly Pittsburgh Home! From US $165
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
King Bed - Heart of PB - Jaw-Dropping Rooftop and Gym From US $72
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Accessibility
424 Gold Way-Apt. 302 From US $217
         

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9.8 (23 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Peaceful Escape Just Minutes To DT, Garage Parking From US $255
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Entire Home Lux Master Terraces 4 Car From US $482
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely Strip District loft with free parking From US $152
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Hydee's Hideaway From US $364
         

10.0 (25 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Luxe Campus Retreat – Sauna, Theater, Park & Walk From US $521
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Squirrel Hill

Over 146+ Large Vacation Homes & Villas in or Near Squirrel Hill
Perfect Place and Breakfast Too! From US $409
         

9.8 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
City Skyline - Outside decks - Contemporary From US $407
         

10.0 (5 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
Family-Friendly Shadyside Gem Near Dtwn Pittsburgh From US $365
         

The Victoria From US $271
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Squirrel Hill

Over 272+ Wheelchair Accessible Vacation Homes in or Near Squirrel Hill
Industrial Loft 5 min to UPMC Shadyside CMU Pitt, sleeps 4 From US $200
         

LUX Studio King Bed Free Parking PITT CMU From US $233
         

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9.4 (5 Reviews)
Apartment
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  • Pet Friendly
  • TV
424-Apt. 403 From US $188
         

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9.6 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Ultra Modern Strip District Suite From US $205
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
HULU+Parking+GYM Near UPMC|Universities|Shopping From US $161
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
PARKING+HULU+GYM Near Universities|UPMC|Shopping From US $156
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
HULU+PARKING+GYM Near Universities|UPMC|Shopping From US $155
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
1BR/1BA with Gym Access Near UPMC & Carnegie Uni. From US $135
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Squirrel Hill Varoom and Airbnb Places to Stay Under $200

Over 669+ Squirrel Hill Varoom and Airbnb Places to Stay Under $200
Chic Modern 2BR Apartment in Carson by Stay Gia From US $109
         

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9.0 (4 Reviews)
Apartment
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  • Parking
  • Child Friendly
Melwood Suites Unit 107 Studio From US $152
         

9.4 (40 Reviews)
Apartment
  • Parking
  • Child Friendly
  • Internet
Historic Home In The South Side From US $182
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area From US $97
         

New Chic Condo in Pittsburgh From US $165
         

10.0 (25 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Squirrel Hill

Over 678+ Instantly Bookable Vacation Homes in or Near Squirrel Hill
King Bed | Free Parking | Arcade | Fire Pit From US $224
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Secret Garden by Frick Park with Garage Parking From US $188
         

10.0 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Squirrel Hill Vacation Rentals

With more than 6 Squirrel Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Squirrel Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Squirrel Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Squirrel Hill. Places to stay near Squirrel Hill are 308.51 ft² on average, with prices averaging $298 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Squirrel Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Squirrel Hill

Type Count
Cottages 5
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Squirrel Hill

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Squirrel Hill.

Weather in Squirrel Hill

View the weather forecast for Squirrel Hill before booking your Squirrel Hill Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F