Best Vacation Homes in Jamaica Plain
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
Jamaica Plain Luxury Rentals
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- TV
- Balcony/Terrace
- Air Conditioner
- TV
- Balcony/Terrace
Jamaica Plain Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
Jamaica Plain Large Vacation Homes
- Air Conditioner
- Security/Safety
- Bedding/Linens
Why Choose Rent By Owner for your Jamaica Plain Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Jamaica Plain Vacation Rentals
Where are the best neighborhoods to stay in Jamaica Plain?
When choosing a neighborhood in Jamaica Plain, Boston, Massachusetts, you’ll find a vibrant community that offers a perfect blend of urban charm and natural beauty. This area is known for its lush parks, diverse dining options, and a welcoming atmosphere that makes it an ideal place to stay during your visit. Whether you're seeking a serene retreat or an energetic neighborhood with local character, Jamaica Plain provides a variety of options for comfortable and convenient vacation rentals. Explore the neighborhood’s unique sense of community while enjoying easy access to Boston’s attractions, all from a thoughtfully selected accommodation in this dynamic part of the city.
Mission Hill
This neighborhood offers a blend of vibrant urban life and scenic views, making it an ideal spot to explore and find comfortable vacation rentals in Boston. Its proximity to the city’s attractions provides easy access for travelers seeking convenience and local culture.
View 3216+ Rentals in Mission HillHighland Park
Known for its lush landscapes and historic charm, this area is perfect for those seeking peaceful surroundings while still being close to the city center. Vacation rentals here offer a tranquil retreat amidst the natural beauty of Boston’s landscapes.
View 28+ Rentals in Highland ParkJamaica Hills - Pond
This neighborhood features scenic ponds and quiet streets, providing a relaxing environment for visitors looking for comfortable accommodations near outdoor spaces. It’s an excellent choice for travelers wanting a peaceful stay with easy access to the region’s parks.
View 25+ Rentals in Jamaica Hills - PondEgleston Square
A vibrant community hub, Egleston Square offers a lively atmosphere combined with convenient transportation options. Here, you can find vacation rentals that place you right in the heart of local culture and accessibility.
View 2141+ Rentals in Egleston SquareHyde Square
Boasting diverse eateries and a lively neighborhood vibe, Hyde Square provides an authentic Boston experience. The area’s accommodations cater to travelers eager to immerse themselves in the city’s multicultural scene.
View 2599+ Rentals in Hyde SquareForest Hills - Woodbourne
Set in a residential area with ample green space, this region offers a peaceful setting for those seeking a comfortable stay within reach of Boston’s attractions. Vacation rentals here provide a serene escape with excellent transit links.
View 624+ Rentals in Forest Hills - WoodbourneBrook Farm
Rich in history and characterized by its charming architecture, this neighborhood is ideal for visitors interested in exploring Boston’s cultural heritage from a convenient base. Nearby vacation rentals make it easy to enjoy the best of the region.
View 176+ Rentals in Brook FarmBest Times to Visit Jamaica Plain
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this vibrant region can greatly enhance your experience, allowing you to enjoy its unique atmosphere and local events at their best throughout the year.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy pleasant weather and vibrant local events that draw visitors to this diverse region.
Early Fall (September to October)
This time offers mild temperatures and fewer crowds, making it ideal for exploring the area's cultural and outdoor attractions.
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather, but also a quieter atmosphere perfect for those seeking a more relaxed visit.
Early Spring (March to April)
As the region transitions from winter, fewer visitors explore here, offering peaceful surroundings for your stay.
Weekly Weather Forecast for Jamaica Plain
How to Book Your Jamaica Plain Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Jamaica Plain
Common Vacation Rentals Amenities
What amenities can you expect?
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 private outdoor spaces such as gardens or patios to relax and unwind in the fresh air.
- Take advantage of access to nearby parks or green areas for outdoor activities during your stay.
- Benefit from outdoor seating areas perfect for dining al fresco or enjoying morning coffee.
- Find properties with outdoor grills or barbecue facilities for gatherings with friends or family.
- Look for vacation rentals that offer outdoor fire pits for cozy evenings under the stars.
- Stays that include bicycle storage or bike-friendly amenities to explore the area on two wheels.
- Check for outdoor recreational features like walking trails or open spaces to enjoy here in the region.
Top Attractions Around Jamaica Plain
What attractions are nearby?
Within this vibrant area, you'll find a variety of outdoor parks, cultural spots, and local shops to explore, providing ample opportunities to enjoy a relaxed yet engaging experience during your stay.
Family Activities
- Arnold Arboretum: Explore this expansive botanical garden to enjoy outdoor family walks and educational programs amid diverse plant collections.
Adult Activities
- Explore Arnold Arboretum: Wander through this expansive botanical garden to enjoy peaceful walking trails and lush plant collections right in the area's natural setting.
- Visit the Boston Nature Center: Engage with local wildlife and discover scenic views at this nearby nature reserve, perfect for outdoor activities and relaxation.
- Discover local art at the Jamaica Plain Arts Center: Immerse yourself in creative exhibitions and participate in workshops that showcase the area's vibrant artistic community.
- Enjoy a cultural performance at local theaters: Experience the region's lively arts scene with live performances ranging from theater productions to music shows in nearby venues.
Other Places to Stay in Jamaica Plain, MA
Jamaica Plain Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Eateries: Savor the diverse culinary scene by visiting neighborhood cafes and restaurants that showcase authentic flavors here.
- Discover Neighborhood Parks: Take advantage of nearby parks to relax, enjoy outdoor activities, and experience the area's vibrant community atmosphere.
- Use Public Transportation: Maximize your stay by utilizing accessible public transit options to easily explore Boston’s cultural and historical sites from your rental.
- Engage with Community Events: Check out local events or markets to immerse yourself in the region’s lively culture and connect with friendly residents during your visit.
Transportation Options
- Green Line T Service: The area's light rail system offers quick and convenient access to downtown Boston and surrounding neighborhoods, making it easy for you to explore the city from your vacation rental.
- Bus Transportation: Multiple bus routes serve the region, providing affordable and reliable connections within the neighborhood and to key attractions in Boston.
- Commuter Rail: The nearby commuter rail stations connect you directly to Boston’s broader transit network, ideal for day trips or commuting to work while staying here.
- Bike Sharing Programs: Public bike-sharing options are available, allowing you to enjoy a scenic and eco-friendly way to explore this vibrant part of Boston at your own pace.
Local Customs Options
- Community Coffee Culture: Embrace the local tradition of enjoying a freshly brewed cup at neighborhood cafes, which are integral to the area's social fabric.
- Green Space Respect: Be mindful of the community’s commitment to parks and outdoor spaces, often gathering spots for residents and visitors alike.
- Neighborhood Art Appreciation: Notice the vibrant street murals and public art installations that reflect the region’s creative spirit and diverse heritage.
- Participate in local dining customs by trying regional dishes and engaging with the community through shared meals or food festivals.
Frequently Asked Questions About Jamaica Plain?
1. What are the top vacation rentals in Jamaica Plain?
There are a lot of options in Jamaica Plain. If you plan on staying in the Jamaica Plain area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Jamaica Plain:
- Airy new apt for 2-6. Off-street parking. Walk to shops/restaurants/subway/bus
- Rare Find in Boston's Hippest Neighborhood
- Victorian house, clean comfortable and well located
- Charming Tree Top Victorian - Two Bedroom Retreat
- Mid-Century Glam Retreat, Near T
- Charming room in a 2-bedroom townhome with AC, WiFi in fantastic central Boston
- Park-Side Home in Jamaica Plain
- Huge Pondside home- Perfect spot to enjoy Boston for week of the 4th!
- Sweet House with yard at prime location
- AMAZING High Ceiling 3 BED/2 BATH Water view
2. Which vacation homes in Jamaica Plain are best for families?
If you are looking for a family-friendly vacation home in Jamaica Plain, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Jamaica Plain:
3. How many Rentbyowner vacation rentals are available in Jamaica Plain?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 75 in the Jamaica Plain 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 Jamaica Plain.
