Jamaica Plain holiday lettings

We found 77 holiday rentals — enter your dates for availability

Discover a selection of 11 homes, 21 apartments and other holiday rentals in Jamaica Plain that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
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Find out more about Jamaica Plain

Find out more about Jamaica Plain

Why visit Jamaica Plain

  • Cultural experiences: Immerse yourself in Jamaica Plain's vibrant arts scene and discover its rich history.
  • Scenic parks: Enjoy the lush greenery of local parks, perfect for leisurely strolls and family outings.
  • Historical colleges: Explore the nearby prestigious educational institutions that add charm to the neighbourhood.
  • Friendly locals: Experience the warm hospitality of the community, enhancing your visit with local insights.
  • Diverse accommodation: Choose from a variety of charming rentals, ensuring a comfortable and enjoyable stay.

Popular types of accommodation around Jamaica Plain

You’ve chosen Jamaica Plain for your getaway, and now it's time to select your perfect accommodation. From charming apartments and houses to stylish condos, there’s a variety of rental options to suit your needs. Explore our selection of Jamaica Plain rentals, including apartment rentals and house rentals, to ensure your stay is comfortable and enjoyable.

  • Apartments: The top choice for holidaymakers in Jamaica Plain, offering a comfortable and convenient base for your stay.
  • Houses: A popular option for those seeking spacious accommodation, perfect for families or groups.
  • Condos: A fantastic alternative for visitors, these stylish living spaces provide a blend of comfort and modern amenities.
  • House Boats: For a unique experience, consider staying on a houseboat, adding a touch of adventure to your trip.
  • Cottages: These charming retreats offer a cosy atmosphere, ideal for a relaxing getaway.**

Top attractions near Jamaica Plain

Jamaica Plain offers a vibrant blend of culture, sport, and business-themed attractions, making it an ideal holiday destination. Visitors can explore historic colleges and universities, lush urban parks, and modern educational institutions. This area caters to those seeking cultural experiences, family outings, and city adventures, ensuring there's something for everyone in this charming Boston neighbourhood.

  • Fenway Park: A historic sports stadium, Fenway Park is famed for its iconic Green Monster. Experience the electric atmosphere of a Red Sox game, immersing yourself in Boston's rich sports culture.
  • Harvard University: As one of the world’s most prestigious institutions, Harvard University boasts stunning architecture and lush grounds. Enjoy a leisurely stroll while soaking in the vibrant academic culture.
  • Boston Common: This expansive urban park is perfect for families and outdoor lovers. Experience the serene beauty of nature amidst the bustling city, ideal for picnics and leisurely walks.

Things to do recommended for couples

For a romantic getaway in Jamaica Plain, indulge in live music at the House of Blues Boston, just 1.9km away. Explore the arts at the Roxbury Center for Arts, 1.2km away, or hit the slopes together at Blue Hills Ski Area, located 4.3km from your base.

Things to do recommended for families

Families visiting Jamaica Plain can enjoy a thrilling experience at Agganis Arena, just 1.9km away, and relax at the scenic Larz Anderson Park, located only 621m away. Don’t miss a sweet treat at Wilbur's North, 11.2km from Jamaica Plain, perfect for family bonding.

Things to do recommended for groups

Experience the vibrant atmosphere of Harvard Square, a bustling shopping centre just 2.5km away. Enjoy a tour and tasting at Samuel Adams Brewery, located 373m away, or catch a film at the charming Coolidge Corner Theatre, a mere 1.2km from Jamaica Plain.

What do I need to keep in mind when booking a vacation around Jamaica Plain

When planning your travels, whether you’re going with a group, family, pets, or seeking longer stays, it’s important to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Jamaica Plain with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Jamaica Plain with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Jamaica Plain: For many, a family holiday isn’t truly complete without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Jamaica Plain: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Jamaica Plain

Jamaica Plain, a vibrant neighbourhood in Boston, offers a delightful mix of culture, history, and friendly locals. Visitors can immerse themselves in the area's family-friendly atmosphere while exploring nearby attractions. From charming rentals to scenic parks, Jamaica Plain serves as an ideal base for your adventures. With its urban vibe and historical significance, this neighbourhood promises a memorable experience for all types of travellers seeking to uncover the essence of Boston.

  • Brookline: Brookline is a charming city located 621m from Jamaica Plain, known for its rich cultural scene and vibrant community. This area offers a delightful mix of educational institutions, music events, and shopping opportunities. Visitors can explore landmarks such as historic colleges and sports stadiums, making it an ideal destination for sports enthusiasts and culture aficionados alike. Brookline's picturesque streets and parks provide a pleasant backdrop for leisurely strolls, while its diverse dining options cater to various tastes.
  • Egleston Square: Just 435m from Jamaica Plain, Egleston Square is a lively neighbourhood brimming with cultural experiences. This area is perfect for those interested in the arts, featuring a variety of music concerts and theatrical performances. The neighbourhood is also home to a modern college university and sports venues, appealing to both students and sports fans. Egleston Square's vibrant atmosphere invites exploration, with its eclectic mix of shops and eateries providing a taste of local flavour.
  • Jamaica Hills - Pond: Located a mere 435m from Jamaica Plain, Jamaica Hills - Pond offers a unique blend of culture, sports, and business opportunities. Visitors can enjoy a range of activities including music concerts and shopping at local centres. The area is highlighted by its proximity to historic sports stadiums and a modern college university, making it a hub for both education and recreation. Jamaica Hills - Pond's scenic environment, complete with parks and ponds, adds to its appeal, providing a tranquil escape within the bustling city.

Best time to go to Jamaica Plain

If you're planning a trip to Jamaica Plain, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnySlightly HighSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowSlightly High
November44.4°F (6.9°C)Light RainMostly SunnySlightly LowAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings since prices fluctuate. Moreover, extending your stay often results in even better deals. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo's ingenious Trip Board offers you an organised space to plan new journeys, pick up from where you last left off, or manage your existing travel arrangements. You can easily locate properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Jamaica Plain?
In Jamaica Plain, apartments are the most popular type of holiday rental, with around 20 available throughout the neighbourhood. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and often access to communal outdoor spaces for relaxing. Many are situated near local parks and vibrant spots like the Arnold Arboretum, making them ideal for those wanting to explore the area's natural beauty.
Are there any beach house rentals in Jamaica Plain?
In Jamaica Plain, Massachusetts, several beach house rentals are available, primarily concentrated near the scenic Jamaica Pond and the Arnold Arboretum. These properties often feature charming, spacious layouts with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups seeking a comfortable stay. Many rentals also include outdoor spaces, such as patios or gardens, superb for enjoying the pleasant surroundings.
How much does it cost to rent a holiday home in Jamaica Plain?
Prices for holiday rentals in Jamaica Plain vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Jamaica Plain to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Jamaica Plain holiday house rentals?
You can find great discounts on house rentals in Jamaica Plain on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Jamaica Plain holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Jamaica Plain with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Jamaica Plain?
A long-stay holiday rental in Jamaica Plain is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Jamaica Plain for a holiday rental?
April is the most popular month to visit Jamaica Plain, making it an excellent choice for travellers looking to experience the vibrant local culture and stunning natural beauty. The peak season spans from March to May, when the cherry blossoms bloom, painting the neighbourhood in shades of pink and attracting visitors eager to take part in outdoor activities and local events.

During this time, temperatures typically range from 10 to 20 degrees Celsius, providing a comfortable climate for exploring the scenic parks and historic sites nearby. Jamaica Plain's picturesque landscapes, including the beautiful Jamaica Pond and the Arnold Arboretum, invite leisurely strolls and picnics, ideal for those who appreciate nature and outdoor fun.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this month falls outside the busy tourist season, it offers a unique charm with festive decorations and a quieter atmosphere for exploring the local cafés and shops.
Are there any remote work holiday rentals in Jamaica Plain?
In Jamaica Plain, there are numerous holiday rentals suitable for remote work, with around 25 options available. This vibrant neighbourhood in Boston is known for its charming parks, such as the Arnold Arboretum and Jamaica Pond, providing a lovely backdrop for breaks during the workday. Many of the properties feature dedicated office spaces or desks, ensuring a comfortable working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Jamaica Plain holiday rental?
Book your Jamaica Plain holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Jamaica Plain?
In Jamaica Plain, visitors can experience a unique blend of urban and natural attractions. The Arnold Arboretum, a part of Harvard University, offers expansive gardens and scenic walking paths, making it a great spot for nature lovers. Many holiday rentals in the area provide easy access to this beautiful green space.

The neighbourhood is also home to the vibrant Centre Street, lined with an array of local shops, cafes, and restaurants that showcase the area's diverse culture. For those interested in the arts, the Jamaica Plain Arts Council hosts various events and exhibitions throughout the year, enriching the local community.
Can I change or cancel my Jamaica Plain home rental booking on Vrbo?
To find Jamaica Plain holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Jamaica Plain holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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