Best Vacation Homes in Brookline
1134 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $4,748/Night
For 7 Nights US $33,237
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
US $586/Night
For 7 Nights US $4,099
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $713/Night
For 7 Nights US $4,988
3068 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,254/Night
For 7 Nights US $8,778
1528.48 ft²
6 Guests
3 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $198/Night
For 7 Nights US $1,387
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $913/Night
For 7 Nights US $6,389
5 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Internet
- Child Friendly
US $684/Night
For 7 Nights US $4,788
9 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $309/Night
For 7 Nights US $2,162
Brookline Luxury Rentals
1462 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $8,861/Night
For 7 Nights US $62,029
2250 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $5,928/Night
For 7 Nights US $41,497
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Internet
US $5,786/Night
For 7 Nights US $40,499
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $5,130/Night
For 7 Nights US $35,910
10763.91 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $4,182/Night
For 7 Nights US $29,274
10 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $3,466/Night
For 7 Nights US $24,259
10763.91 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Air Conditioner
US $3,012/Night
For 7 Nights US $21,084
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $2,970/Night
For 7 Nights US $20,788
Brookline Pet Friendly Vacation Rentals
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $290/Night
For 7 Nights US $2,027
1054.86 ft²
5 Guests
2 Bedrooms
1 Bathroom
House
- View
- Pet Friendly
- Parking
US $235/Night
For 7 Nights US $1,645
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $383/Night
For 7 Nights US $2,679
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $288/Night
For 7 Nights US $2,015
861.11 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $230/Night
For 7 Nights US $1,610
1320 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $197/Night
For 7 Nights US $1,379
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $357/Night
For 7 Nights US $2,497
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $390/Night
For 7 Nights US $2,733
Brookline Large Vacation Homes
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $295/Night
For 7 Nights US $2,066
1506.95 ft²
16 Guests
6 Bedrooms
2 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $468/Night
For 7 Nights US $3,275
2000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $456/Night
For 7 Nights US $3,194
10 Guests
1 Bedroom
1 Bathroom
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $125/Night
For 7 Nights US $875
3000 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $659/Night
For 7 Nights US $4,613
10 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $222/Night
For 7 Nights US $1,556
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $678/Night
For 7 Nights US $4,744
16 Guests
9 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $799/Night
For 7 Nights US $5,594
Why Choose Rent By Owner for your Brookline Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Brookline
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you can enjoy all that this destination has to offer, making your stay in the region truly memorable and fulfilling.
Peak Season Highlights
Summer (June to August)
During the warmest months, you'll find this destination bustling with activity, making it an ideal time to explore local events and enjoy outdoor activities.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
As the region's foliage reaches its peak, this season offers stunning scenery and a vibrant atmosphere for visitors booking vacation rentals.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
Quiet and peaceful, winter provides a cozy setting perfect for those seeking tranquility while staying in vacation rentals nearby.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Early Spring (March to April)
With fewer visitors, this period offers more affordable rates on vacation rentals and a chance to enjoy the area's emerging spring charm.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Brookline
How to Book Your Brookline Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Brookline
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas or patios perfect for relaxing and entertaining in the region's pleasant climate.
- Benefit from well-maintained gardens or landscaped yards that add curb appeal to your stay.
- Take advantage of private or shared outdoor seating spaces to unwind after exploring the area.
- Make use of outdoor grills or barbecue equipment to prepare delicious meals with ease.
- Find access to nearby parks, walking trails, or green spaces that showcase the natural beauty of this destination.
- Relax on cozy decks or porches that provide picturesque views of the surrounding neighborhood or scenery.
- Utilize parking areas with designated outdoor spaces to conveniently come and go during your visit here.
Top Attractions Around Brookline
What attractions are nearby?
While staying here, you'll have the opportunity to explore nearby parks, cultural attractions, and local dining options that highlight the vibrant atmosphere of this area in Pittsburgh.
Family Activities
- Phipps Conservatory and Botanical Gardens: Discover a stunning array of plants and gardens that inspire exploration and family learning in this renowned conservatory, perfect for a relaxing day out.
- The Children's Museum of Pittsburgh: Engage your family with hands-on exhibits and interactive play designed to entertain and educate children of all ages in this popular regional attraction.
- Frick Park: Enjoy outdoor adventures with walking trails, playgrounds, and picnic areas that make this park an ideal spot for family fun amidst nature here in the city.
- Pittsburgh Zoo & PPG Aquarium: Experience wildlife up close and explore aquatic exhibits as part of a memorable day dedicated to family entertainment in this popular regional destination.
Adult Activities
- Visit the Berkman Plaza for a relaxing day by the water, where you can enjoy scenic views and outdoor activities in this inviting part of town.
- Explore the local cuisine at popular restaurants around the area, offering a taste of authentic flavors unique to here.
- Take a stroll through charming neighborhoods to experience the vibrant architecture and inviting atmosphere that defines this region.
- Enjoy a cultural experience at nearby art galleries and theaters that showcase the region’s artistic talents and entertainment options.
Brookline Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area’s diverse eateries to enjoy authentic regional flavors and support local businesses during your stay.
- Visit Neighborhood Parks: Spend time outdoors at nearby parks to relax and experience the natural beauty that enhances your visit to this destination.
- Utilize Public Transportation: Make the most of the region’s transit systems for easy access to attractions and to avoid parking hassles in this city-focused area.
- Plan Your Activities Ahead: Research local events and must-see spots beforehand to optimize your experience and fully immerse yourself in the neighborhood charm.
Transportation Options
- Pittsburgh Regional Transit (PRT): This comprehensive public transportation system provides convenient bus and light rail services to help you explore the area efficiently.
- Comprehensive Rideshare Services: Popular options like Uber and Lyft are readily available throughout here, offering flexible transportation at your fingertips.
- Car Rentals: Several rental agencies operate nearby, giving you the freedom to discover the region at your own pace with a private vehicle.
- Biking and Scooter Rentals: Shared bikes and electric scooters are an eco-friendly way to navigate local neighborhoods and enjoy outdoor activities here.
Local Customs Options
- Greeting Traditions: Visitors often experience warm welcomes and friendly greetings, reflecting the area's genuine hospitality rooted in local customs.
- Community Celebrations: Participating in neighborhood festivals and events provides an authentic glimpse into the region’s lively cultural spirit.
- Dining Etiquette: The local dining scene emphasizes casual yet respectful manners, highlighting the community’s emphasis on conviviality and shared meals.
- Respect for Local History: Engaging with historical landmarks and respecting preservation efforts is a valued custom here, offering insight into the area's rich past.
Brookline Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Brookline?
There are a lot of options in Brookline. If you plan on staying in the Brookline area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Brookline:
- Urban Retreat with Garage on Mt. Washington
- View from the Top! Steps from Grandview, Sleeps 8
- ★ HostWise Stays ★ Skyline Splendor w/Private Balconies & Game Room
- Monthly Bungalow In Green Tree
- ECLECTIC ● 3 BDRM ▪︎ 3 BATH ▪︎ PATIO ▪︎ EV CHARGER ▪︎ GARAGE ▪︎ MIN TO DNTWN
- Clean and comfortable 3BR home in the South Side neighborhood
- PROFESSIONALLY CLEANED/QUARANTINED
- ★ HostWise Stays ★ Grandview Ave - Private Balcony with Stunning Skyline Views!
- Historic Home In The South Side
- Peaceful full home in the heart of Southside Flats.
2. How many vacation rentals have private pools in Brookline?
There are 5 vacation rentals with private pools near Brookline. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Brookline are best for families?
If you are looking for a family-friendly vacation home in Brookline, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Brookline:
4. How many Rentbyowner vacation rentals are available in Brookline?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 904 in the Brookline area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Brookline.
5. What is the cancellation policy for vacation rentals in this area?
The cancellation policies vary by listing, so it's important to review the specific property's terms before booking. You can find detailed information on the rental's page or contact the owner directly for clarification.
6. How do I confirm my reservation at a vacation rental nearby?
Reservations are confirmed once you complete the booking process and receive a confirmation email. For any questions about your reservation status, reach out to the property owner through the platform's messaging system.
7. Are there any house rules or amenities I should be aware of during my stay?
Each vacation rental has its own set of house rules and available amenities listed on the property page. Be sure to review these details before confirming your reservation to ensure the property meets your needs.
8. What is the check-in and check-out process for vacation rentals here?
Check-in and check-out procedures are specified in the listing details. Many properties offer flexible check-in times, but it’s best to communicate with the owner for personalized instructions or if you have special timing requests.
9. Is using a credit card secure when booking a vacation rental in this location?
Yes, the booking platform employs secure payment methods to protect your financial information. Confirm all payment details via the trusted platform, and contact the owner if you have any concerns regarding payment security.
Brookline Top Rated Vacation Rentals
2000 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $118/Night
For 7 Nights US $824
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $128/Night
For 7 Nights US $899
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $173/Night
For 7 Nights US $1,213
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $139/Night
For 7 Nights US $974
387.5 ft²
47 Guests
108 Bedrooms
5 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $200/Night
For 7 Nights US $1,402
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $96/Night
For 7 Nights US $670
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $107/Night
For 7 Nights US $750
453.43 ft²
52 Guests
212 Bedrooms
14 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $305/Night
For 7 Nights US $2,135
