Discover Your Perfect Brookline Vacation Homes

Brookline Luxury Rentals

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Brookline Large Vacation Homes

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8.1 (37 Reviews)
Apartment
Furnished Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
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Why Choose Rent By Owner for your Brookline Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Brookline Vacation Rentals

Where are the best neighborhoods to stay in Brookline?

When choosing neighborhoods to stay in within Brookline, Massachusetts, you’ll find a variety of charming areas that offer convenient access to Boston while maintaining a unique, local atmosphere. Each neighborhood provides its own blend of historic charm and modern amenities, making it an ideal base for exploring the city. Whether you prefer the lively streets and vibrant community spirit or a quieter, residential setting, Brookline offers the perfect location for your vacation rental experience. Booking a property in these neighborhoods ensures you enjoy a comfortable, accessible, and authentic stay in this welcoming Massachusetts community.

Fenway–Kenmore

In this vibrant area, you'll find a lively atmosphere close to renowned sports venues and cultural hotspots, making it an ideal choice for those seeking entertainment and city living. The neighborhood's convenient location offers easy access to public transportation and popular attractions.

View 191+ Rentals in Fenway–Kenmore

Jamaica Plain

Known for its lush parks and eclectic vibe, this neighborhood provides a peaceful retreat within the city where you can enjoy green spaces and unique local shops. Here, you’re surrounded by a welcoming community with a rich cultural scene.

View 37+ Rentals in Jamaica Plain

Brighton

This region offers a relaxed suburban feel while still being close to the city's main attractions, appealing to those who value convenience and a friendly atmosphere. With numerous dining options and outdoor activities, it’s perfect for exploring at your own pace.

View 95+ Rentals in Brighton

Cleveland Circle

Offering quick transit connections and nearby recreational areas, this area is a great base for travelers wanting accessibility to downtown and beyond. It combines a vibrant community with practical amenities for comfortable stays.

View 79+ Rentals in Cleveland Circle

Longwood

This neighborhood is renowned for its historic charm and proximity to medical and educational institutions, making it an excellent choice for those visiting for studies or professional purposes. Its tree-lined streets add to the area's inviting ambiance.

View 3484+ Rentals in Longwood

Mission Hill

Perched on higher ground, this destination boasts impressive views and a diverse community atmosphere. It offers easy access to the city’s cultural sites and is suited for travelers interested in exploring Boston’s vibrant arts and dining scenes.

View 3442+ Rentals in Mission Hill

Emerson Gardens

Surrounded by greenery and tranquil streets, this area offers a serene environment away from the hustle and bustle, perfect for relaxing after busy days of sightseeing. Its charming residences enhance the neighborhood's peaceful appeal.

View 2391+ Rentals in Emerson Gardens

Aspinwall Hill

With its historic homes and scenic views, Aspinwall Hill provides a picturesque setting for your stay, blending classic architecture with natural beauty. It’s ideal for visitors seeking a quiet, yet accessible neighborhood.

View 1869+ Rentals in Aspinwall Hill

Best Times to Visit Brookline

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you enjoy this destination’s unique atmosphere and attractions at their best, making your stay in the area truly memorable.

Peak Season Highlights

summer
Summer (June - August)

During the warmest months, you'll enjoy the region's lively atmosphere and extended daylight hours, perfect for exploring local sights and culture.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Fall (September - November)

The crisp air and stunning foliage make this time ideal for outdoor activities and sightseeing, adding charm to your stay in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December - February)

This quieter period offers a peaceful retreat with cooler temperatures, perfect for cozying up indoors or enjoying less crowded surroundings.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Spring (March - May)

As nature begins to bloom, you can experience fewer visitors and enjoy milder weather while exploring this destination's scenic beauty.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°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

More Top-Rated Vacation Rentals in Brookline Area

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 a private outdoor seating area perfect for relaxing after exploring the region.
  • Take advantage of shared or private gardens that showcase the area's lush greenery and seasonal blooms.
  • Make use of outdoor dining spaces ideal for savoring local cuisine under the open sky.
  • Benefit from nearby walking trails and pathways that invite you to experience the natural beauty of this destination.
  • Relax in outdoor lounge areas designed for entertaining or unwinding with friends and family.
  • Utilize parking spaces with easy access to outdoor amenities, making your stay more convenient in the region.
  • Discover outdoor recreational facilities such as courtyards or play areas that cater to all ages during your visit here.

Top Attractions Around Brookline

What attractions are nearby?

In the surrounding area, you can enjoy a diverse range of activities such as exploring scenic parks, visiting local cultural sites, and dining at charming eateries, all conveniently accessible from your vacation rentals here in Brookline, Massachusetts.

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Family Activities

  • Boston Museum of Fine Arts: Engage your family with a visit to one of the region’s top art museums, offering captivating exhibits and interactive activities for all ages.
  • Brookline’s Coolidge Corner: Explore this vibrant neighborhood filled with family-friendly cafes, shops, and historic sites that showcase the area's cultural charm.
  • Larz Anderson Park: Enjoy outdoor fun at this scenic park featuring sprawling lawns, a historic carriage museum, and space for picnics and play.
  • John F. Kennedy National Historic Site: Discover the childhood home of the President, providing an educational experience that highlights both history and the region’s significance.
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Adult Activities

  • exploring local art galleries and museums: Discover the region's vibrant cultural scene through art exhibits and historical collections that showcase its rich heritage.
  • strolling through scenic parks and gardens: Enjoy relaxing walks in beautifully maintained green spaces perfect for unwinding and soaking in the area's natural beauty.
  • experiencing renowned culinary scenes: Indulge in diverse dining options that highlight the region’s flavorful cuisines and offer a taste of local traditions.
  • visiting historic landmarks and estates: Tour iconic sites and architectural marvels that tell the story of this destination’s storied past and community development.

Other Places to Stay in Brookline, MA

Photographic Resource Center
Photographic Resource Center Vacation Rentals
Longwood
Longwood Vacation Rentals
Agganis Arena
Agganis Arena Vacation Rentals
Paradise Rock Club
Paradise Rock Club Vacation Rentals
Central Village
Central Village Vacation Rentals
Coolidge Corner South Side
Coolidge Corner South Side Vacation Rentals
Emerson Gardens
Emerson Gardens Vacation Rentals
High Street Hill
High Street Hill Vacation Rentals
Corey Hill
Corey Hill Vacation Rentals
Aspinwall Hill
Aspinwall Hill Vacation Rentals
Griggs Park
Griggs Park Vacation Rentals
North Brookline
North Brookline Vacation Rentals
More Places to Stay Near Brookline

Brookline Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region's diverse culinary scene to enjoy authentic local flavors during your stay.
  • Plan Convenient Transportation: Utilize nearby public transit or consider renting a bike to easily access attractions and amenities in this area.
  • Discover Hidden Gems: Venture beyond typical tourist spots to uncover unique shops and peaceful parks that showcase the charm of the destination.
  • Schedule Flexible Activities: Keep your itinerary adaptable, allowing you to immerse yourself fully in the relaxed pace and vibrant community here.

Transportation Options

  • Boston Logan International Airport: You can easily access the region from this major airport, which offers numerous domestic and international flights, making your travel to Brookline straightforward.
  • MBTA Green Line Subway: This reliable subway service connects you directly to Boston and surrounding neighborhoods, providing convenient transit options for exploring here.
  • Commuter Rail Services: The regional rail network links the area to downtown Boston and beyond, offering a comfortable way to travel without hassle.
  • Shared Rides and Taxis: Easily available throughout the region, these transportation options provide flexible and direct routes to your vacation rental in Brookline or nearby attractions.

Local Customs Options

  • Respect for Local Heritage: When visiting the area, you'll notice a strong appreciation for preserving its historic architecture and cultural landmarks.
  • Community Gatherings: Engaging in neighborhood events and local festivals is a cherished custom here, fostering a sense of belonging among residents and visitors alike.
  • Environmental Consciousness: Recycling practices and eco-friendly initiatives are widely embraced, reflecting the area's dedication to sustainability.
  • Dining Etiquette: Locals often gather casually at neighborhood cafes and restaurants, emphasizing friendliness and relaxed social interactions characteristic of this destination.

Frequently Asked Questions About Brookline?

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:

2. 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:

3. How many Rentbyowner vacation rentals are available in Brookline?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 317 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. 

4. What is the cancellation policy for vacation rentals in Brookline, Massachusetts?

Cancellation policies vary by property. To understand the specific terms and any potential fees, please review the listing details or contact the property owner directly before completing your reservation.

5. Are there any amenities or services included with the rental stay in Brookline?

Amenities differ between properties, so it's important to check the listing description for details on what's included, such as Wi-Fi, parking, or kitchen facilities. You can also reach out to the host for additional questions.

6. How do I confirm my booking at a vacation rental in the area?

Booking confirmation typically occurs after completing the reservation process and payment. However, some listings may require owner approval beforehand, so be sure to review the reservation status in your account or contact the host if needed.

7. What are the check-in and check-out times for vacation rentals here?

Check-in and check-out times are specified in each property's listing. Confirm these details during booking, and contact the host if you need special arrangements or have specific timing requests.

8. Is it possible to modify or cancel my reservation for a rental in this region?

Modifications and cancellations depend on the individual property's policies. Please refer to the listing’s terms or contact the owner directly to discuss any changes to your reservation.