Discover Your Perfect Longwood Vacation Homes

Why Choose Rent By Owner for your Longwood 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 Longwood Vacation Rentals

Where are the best neighborhoods to stay in Longwood?

When exploring neighborhoods to stay in Longwood, Brookline, Massachusetts, you'll find that this area offers a welcoming blend of urban convenience and charming residential streets. Located close to many local amenities, the neighborhood provides easy access to the vibrant community atmosphere that makes Brookline a desirable place to visit. Whether you prefer a quiet, tree-lined street or a lively locale with nearby shops and cafes, there are plenty of options for a comfortable and convenient stay. Choosing a location within Longwood, Brookline ensures you enjoy a seamless experience, combining accessibility with the cozy ambiance of this well-loved Boston suburb.

Coolidge Corner South Side

In this vibrant area, you’ll find a welcoming atmosphere combined with convenient access to local amenities, making it an ideal choice for your stay in Brookline. The neighborhood offers easy proximity to public transportation and charming streets, perfect for exploring the region’s unique character.

View 2759+ Rentals in Coolidge Corner South Side

Best Times to Visit Longwood

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you enjoy the region's charm at its best, whether you're seeking lively local events or peaceful moments in this destination's inviting atmosphere.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, you'll enjoy pleasant weather ideal for exploring the region’s outdoor spaces and authentic local experiences. The area tends to be lively as visitors take advantage of the warm days and extended daylight hours.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This period offers mild temperatures and vibrant foliage, making it an excellent choice for travelers who prefer a comfortable climate. The region's scenic beauty peaks, attracting those seeking picturesque surroundings and peaceful stays in vacation rentals.

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

Off-Season Highlights

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Winter (December to February)

During the colder months, fewer visitors come here, providing a cozy atmosphere perfect for relaxing indoors or enjoying quieter outdoor activities. Vacation rentals tend to be more available, often at better rates.

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

As the region begins to thaw, you can experience fewer crowds and lower prices. It's an ideal opportunity for those seeking an authentic, less busy visit while still enjoying some of the early signs of spring.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Longwood

How to Book Your Longwood 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 Longwood

More Top-Rated Vacation Rentals in Longwood 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 outdoor dining areas perfect for summer meals in the region’s pleasant climate.
  • Relax in private yards or gardens that offer a peaceful retreat after exploring the local attractions.
  • Take advantage of outdoor seating and lounge spaces for relaxing with friends or family.
  • Benefit from accessible parking facilities to make your arrival and departure hassle-free.
  • Make use of outdoor grills or barbecue setups for casual cookouts in the area’s inviting outdoor spaces.
  • Explore nearby walking trails or green spaces that are often part of the property’s outdoor amenities.
  • Discover shaded patios or verandas, ideal for enjoying the fresh air during your stay here.

Top Attractions Around Longwood

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor and cultural activities, from exploring scenic parks to engaging with local arts and history, making it an ideal destination for a diverse and enriching stay.

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Family Activities

  • Longwood Playground: Enjoy a fun-filled day at this family-friendly park, featuring playgrounds and open spaces perfect for outdoor activities.
  • Brookline Community Center: Participate in engaging arts, sports, and educational programs designed to entertain children and bring families together.
  • The Massachusetts Historical Society Museum: Discover interactive exhibits that introduce young visitors to the rich local history of the area.
  • Brookline Corners Skate Park: Experience an exciting day skateboarding and practicing tricks at this popular outdoor skate park suitable for all skill levels.
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Adult Activities

  • Longwood Medical Area Exploration: Discover some of the region’s most renowned medical institutions and research centers in this vibrant neighborhood, perfect for those interested in health sciences or academic pursuits.
  • Brookline’s Historic Walking Tours: Engage with the area's rich history by strolling through historic districts and landmarks that showcase the charming architecture and cultural heritage of this part of Massachusetts.
  • Local Dining Experiences: Savor an array of dining options offering diverse cuisines that highlight the culinary scene here, ideal for adults seeking authentic regional flavors.
  • Recreational Parks and Green Spaces: Enjoy outdoor activities and relaxation in nearby parks, providing a peaceful retreat amidst the bustling city environment.

Longwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take the time to visit popular spots in the area to fully experience the unique charm of this destination.
  • Plan Ahead for Dining: Research nearby restaurants and cafes to enjoy authentic local cuisine during your stay.
  • Utilize Public Transportation: Make the most of accessible transit options to easily navigate between attractions without hassle.
  • Book Early for Peak Seasons: Reserve your vacation rentals well in advance to secure the best accommodations during busy travel times.

Transportation Options

  • Public Transit (MBTA): The Massachusetts Bay Transportation Authority provides convenient subway and bus options, making it easy to explore the area without a car.
  • Commuter Rail: With commuter rail services connecting to Boston and surrounding regions, you can enjoy stress-free travel to nearby urban attractions.
  • Taxi and Rideshare Services: Taxis and popular rideshare apps offer reliable transportation throughout here, providing flexibility for your daily adventures.
  • Car Rentals: Local rental agencies allow you to explore the region at your own pace, especially if you prefer private transportation during your stay.

Local Customs Options

  • Respect for Local History: When visiting here, you’ll find that residents take pride in preserving the area's rich historical heritage through various community traditions.
  • Community Festivals: Participating in seasonal festivals and events is common, reflecting a friendly and welcoming spirit that defines the region’s cultural identity.
  • Educational Engagement: Education and knowledge-sharing are highly valued, often celebrated through local gatherings and museum visits that showcase the area's past.
  • Friendly Greetings: Expect to experience warm and courteous interactions with locals, as politeness and friendliness are customary in this community-oriented destination.

Frequently Asked Questions About Longwood?

1. What are the top vacation rentals in Longwood?

There are a lot of options in Longwood. If you plan on staying in the Longwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Longwood:

2. How many vacation rentals have private pools in Longwood?

There are 39 vacation rentals with private pools near Longwood. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Longwood are best for families?

If you are looking for a family-friendly vacation home in Longwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Longwood:

4. How many Rentbyowner vacation rentals are available in Longwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 3491 in the Longwood 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 Longwood. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies can vary depending on the host and specific listing. To ensure you understand the terms, please read the cancellation details provided in the listing or contact the property owner directly for clarification.

6. How do I know if a vacation rental has the amenities I need?

Each listing includes a detailed description of the amenities offered. Review these details carefully to confirm that the property meets your needs, or reach out to the owner with any specific questions.

7. Are there any restrictions or house rules I should be aware of before booking?

Yes, most properties list house rules and restrictions in the description or during the booking process. Be sure to review these rules thoroughly and contact the host if you have any concerns.

8. What is the process for checking in and checking out of vacation rentals in this region?

Check-in and check-out procedures are specified in each listing. Many hosts offer flexible options; however, it’s recommended to verify these details prior to booking by contacting the owner directly.

9. How do I confirm availability and secure my reservation for vacation rentals here?

Availability is shown in real-time for each listing. Once you select your dates, you can proceed with the booking process, which typically involves submitting a reservation request and making a payment to secure your stay.

Longwood Top Rated Vacation Rentals

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10.0 (2 Reviews)
Apartment
South End Club Suites by Orchard
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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