Trippy Mates - Vacation Rentals in Brookline

Historic Home In The South Side From US $210
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Chic Modern 2BR Apartment in Carson by Stay Gia From US $109
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Perfect Place and Breakfast Too! From US $409
         

9.8 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Relax & Feel At Home During Your Pittsburgh Stay From US $148
         

9.4 (32 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Urban Retreat with Garage on Mt. Washington From US $174
         

10.0 (71 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
View from the Top! Steps from Grandview, Sleeps 8 From US $242
         

10.0 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Brookline

Over 858+ Luxury Places to Stay in or Near Brookline
5BDRM GEM with Arcade - Mt Wash From US $4,182
         

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The Cityview Getaway Mt Washington From US $2,314
         

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New
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6BDRM with Hot Tub Mt Wash From US $2,252
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
Skyline Serenity Downtown From US $1,358
         

New
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  • Pet Friendly
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Charming 1BR: Steps to Football Fun! From US $1,358
         

New
Apartment
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  • Pet Friendly
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Brookline

Over 21+ Top-Rated Vacation Rentals with a Pool in or Near Brookline
Monthly Bungalow In Green Tree From US $118
         

10.0 (52 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Convenient to DT, Airport, Stadiums-Free Parking! From US $133
         

Sheraton Pittsburgh Hotel at Station Square From US $173
         

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9.0 (1027 Reviews)
Hotel
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  • Parking
  • Pool
SpringHill Suites by Marriott Pittsburgh Mt. Lebanon From US $185
         

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8.8 (105 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Inn & Suites Pittsburgh South From US $102
         

8.6 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Pittsburgh West - Greentree by IHG From US $120
         

Pet-Friendly Vacation Rentals in Brookline

Over 399+ Pet-Friendly Vacation Rentals in or Near Brookline
Entire Home Lux Master Terraces 4 Car From US $367
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Southside Pitt home w/Pool Table +Yard From US $198
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Sleek 2BR Downtown Retreat with Gym From US $713
         

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10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Historic 2BR Loft: Private Terrace & Free UFC Gym From US $338
         

10.0 (24 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
HOT TUB Cozy Woodsy retreat close to the City From US $276
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Southside Pitt home w/Pool Table +Yard From US $271
         

10.0 (9 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Brookline

Over 141+ Large Vacation Homes & Villas in or Near Brookline
Luxury Pittsburgh Home with Incredible View From US $575
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • TV
  • Wheelchair Accessible
City Skyline - Outside decks - Contemporary From US $407
         

10.0 (7 Reviews)
House
  • Parking
  • Security/Safety
  • Fireplace/Heating
Central 5BD Getaway - Spacious Home w/BBQ From US $442
         

4bd Pittsburgh Escape: BBQ, Games, 10mins to UPitt From US $327
         

Pittsburgh Gem - 5BR - Downtown Deck View From US $526
         

City Skyline - Outside decks - Contemporary From US $415
         

Spacious 8 Bed House! Triple King Bed - 3 Stories! From US $474
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
King Bed Garage Rooftop Views Sleeps 14 Game room walk to Carson St From US $424
         

Wheelchair Accessible Vacation Homes in Brookline

Over 119+ Wheelchair Accessible Vacation Homes in or Near Brookline
Etage Executive Living From US $209
         

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8.7 (420 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxe 2BR Loft Retreat: Private Terrace & Free Gym From US $647
         

Etage Executive Living From US $170
         

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9.2 (1598 Reviews)
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  • Parking
  • Wheelchair Accessible
2BR Downtown Apartment with Gym & Deck From US $275
         

9.8 (24 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Apt 420★Park Free★Great Views From US $221
         

9.6 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Sleek 2BR Downtown Retreat with Gym From US $608
         

9.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Brookline Varoom and Airbnb Places to Stay Under $200

Over 378+ Brookline Varoom and Airbnb Places to Stay Under $200
Charming 3Bed 2&half Bath with Deck & Free Strt Parking From US $196
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cozy&Modern 2Bdr Apt PIttsburgh From US $122
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Grandview Studio | Skyline Views | Private Parking From US $191
         

Southside Flats Cozy Quiet Luxury From US $173
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Plush 4BR Retreat Patio, Great Location From US $189
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Obies Abode: Newly Renovated From US $133
         

10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • TV

Instantly Bookable Vacation Homes in Brookline

Over 418+ Instantly Bookable Vacation Homes in or Near Brookline
Stylish 2BR! Off-Street Parking! From US $243
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Updated Townhome with Private Garage in South Side From US $213
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Brookline Vacation Rentals

With more than 867 Brookline vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trippymates 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 Brookline.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Trippymates Brookline, 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 Brookline. Places to stay near Brookline are 885.17 ft² on average, with prices averaging $294 a night.

Trippymates makes it easy and safe to find and compare vacation rentals in Brookline 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 Brookline

Type Count
Vacation Homes 433
Holiday Apartments 378
Hotels with Suites 39
Villas 4
Cottages 3
B&B 1
Hostels 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Brookline

Pro Tip: Trippymates makes it easy to compare the best listings on Trippymates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trippymates 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 Brookline.

Weather in Brookline

View the weather forecast for Brookline before booking your Brookline 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