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Jamaica Plain Vacation Rentals

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Jamaica Plain
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
House
Pension
Rating
4.5+
4+
3.5+

Uncover an alternative Boston with a Jamaica Plain vacation rental

Vacation rentals in Boston's Jamaica Plain district are characterized by green spaces forming part of the Emerald Necklace and a diverse community. Experience another side of Boston in this verdant retreat, where you'll discover heritage around every leaf-dappled corner.

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Best Vacation Home Deals in Jamaica Plain

Save up to 50%

Apartment Jamaica Plain
Nov 4 - Nov 11
-23%
$318
$244 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Rental Apartment in Brookline Village + Picturesque Views
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Feb 2 - Feb 9
-50%
$503
$250 per night
Condo ∙ 9 guests ∙ 4 bedrooms
Condo in Egleston Square
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Oct 29 - Nov 5
-31%
$266
$183 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Brookline
3.9
Good (12 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Find the ideal property from $96 per night by searching among the 1,342 options being offered in Jamaica Plain. Every one of the accommodations from our partner websites are instantaneously compared by our algorithm so you can save up to 50%.

Top-Rated Rentals and Accommodations in Jamaica Plain

Book Vacation Rental Offers with the Highest User Rating

Apartment Jamaica Plain
Dec 30 - Jan 6
$427 per night
Apartment ∙ 11 guests ∙ 4 bedrooms
Apartment in Franklin Field South
5.0
Outstanding (40 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Dec 9 - Dec 16
$270 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Duplex Rental Apartment in Highland Park with Free Parking
4.6
Excellent (33 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 10 - Nov 17
$255 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
Rental Apartment in Centre-South with Free Parking
4.8
Outstanding (5 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Recommended Vacation Rentals in Jamaica Plain

Find your perfect vacation rental in Jamaica Plain: from $99 per night

Apartment Jamaica Plain
Oct 21 - Oct 28
$147 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Salisbury Road - Corey Farm
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 4 - Nov 11
$186 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Wonderful Apartment in Brookline
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 4 - Nov 11
$244 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
Charming Apartment in Brookline
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 4 - Nov 11
$171 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Brookline with Free Parking
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Jan 19 - Jan 26
-56%
$612
$272 per night
Condo ∙ 12 guests ∙ 4 bedrooms
Condo in Stonybrook
4.0
Very good (1 rating)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 2 - Mar 9
-41%
$414
$245 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Apartment in Jamaica Hills / Pond
4.5
Excellent (32 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 2 - Mar 9
$175 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Sunny Rental Apartment in Centre-South with Yard
5.0
Outstanding (42 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 1 - Mar 8
-49%
$280
$144 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Rental Apartment in Codman Square with Grill & Yard
4.9
Outstanding (117 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Dec 20 - Dec 27
$252 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Rental Apartment in Moreland Street Historic District
4.6
Excellent (19 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Budget-friendly Vacation Rentals in Jamaica Plain

Find Fantastic yet Inexpensive Offers

Apartment Jamaica Plain
Oct 29 - Nov 5
$383 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Apartment in Codman Square
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Dec 9 - Dec 16
$165 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Highland Park
4.8
Outstanding (78 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 4 - Nov 11
$171 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Brookline
Jamaica Plain, Boston, Massachusetts, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 29% of in Jamaica Plain vacation rentals have a swimming pool.

Apartment  Jamaica Plain
Jan 27 - Feb 3
-38%
$714
$441 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Prudential / St. Botolph with Pool
Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Apartment  Jamaica Plain
Jan 28 - Feb 4
-38%
$703
$434 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Pleasant Rental Apartment in Prudential / St. Botolph with Pool
Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Apartment  Jamaica Plain
Jan 15 - Jan 22
-39%
$857
$521 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Rental Apartment in Prudential / St. Botolph with Pool
Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Jamaica Plain!

Apartment  Jamaica Plain
Nov 11 - Nov 18
-19%
$333
$269 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Rental Apartment in Brookline with Electric Fireplace
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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House  Jamaica Plain
Jan 19 - Jan 26
-58%
$458
$193 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming House in Centre-South with Yard
5.0
Outstanding (17 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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Apartment  Jamaica Plain
Dec 16 - Dec 23
-52%
$470
$225 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Egleston Square with Grill & Yard
4.6
Excellent (50 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Jamaica Plain with their own private patios and balconies.

Condo  Jamaica Plain
Mar 16 - Mar 23
$399 per night
Condo ∙ 8 guests ∙ 4 bedrooms
Entire Condo in Egleston Square with Yard
5.0
Outstanding (16 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Apartment  Jamaica Plain
Dec 30 - Jan 6
$259 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Apartment in Washington Park
5.0
Outstanding (13 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Apartment  Jamaica Plain
Mar 16 - Mar 23
$275 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in St. Elizabeth\'s
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Popular Rental Amenities in Jamaica Plain

  • Pet-friendly (303)
  • Parking (155)
  • WiFi (1,291)
  • Washing machine (794)
  • Microwave (825)
  • Pool (411)
  • Fireplace (73)
  • Balcony/patio (244)
  • Dishwasher (532)
  • No smoking (843)
  • TV (1,244)
  • Kitchen (940)

Our search page's filters will help you find the ideal property in Jamaica Plain. In Jamaica Plain, 303 properties provide "Pets allowed". Consequently, if you travel with your pet, use the Pets allowed filter to compare these accommodations. You can also look for a vacation rental in Jamaica Plain if you don't have a dog as 1,035 of the listed properties there provide "No pets allowed."

Price and Availability Index in Jamaica Plain

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Vacation Rental Price Information in Jamaica Plain

This graph displays the average prices for the next twelve months in Jamaica Plain. The week with the highest average prices is in August (8/31 - 9/7). During this week, a night will cost on average $622. The week with the lowest average prices is in December (12/30 - 1/6).

Rental availability information in Jamaica Plain

This graph shows the vacation rental availability rate for the next twelve months. It is harder to find an accommodation during a week of August (8/31 - 9/7), as 74% of the rentals are booked. On the other hand, the week with the most available offers is in December (12/2 - 12/9).

The Weather in Jamaica Plain

max.
Min.
37°
25°
15 days 15
max.
Min.
39°
23°
15 days 15
max.
Min.
46°
30°
14 days 14
max.
Min.
57°
41°
13 days 13
max.
Min.
66°
52°
14 days 14
max.
Min.
75°
59°
13 days 13
max.
Min.
82°
66°
12 days 12
max.
Min.
82°
66°
9 days 9
max.
Min.
73°
59°
9 days 9
max.
Min.
63°
48°
13 days 13
max.
Min.
52°
37°
10 days 10
max.
Min.
45°
32°
17 days 17
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Jamaica Plain. On average, the warmest month is July. On the other hand, you could have temperatures dropping under 23° in February. The rainiest month is December while the driest month is August.

7-Day Weather Forecast in Jamaica Plain

Tue, 26 Sep
62°
55°

0%

5 h

10 mi/h

Wed, 27 Sep
64°
55°

0%

6 h

8 mi/h

Thu, 28 Sep
66°
59°

0%

5 h

10 mi/h

Fri, 29 Sep
68°
59°

0%

5 h

9 mi/h

Sat, 30 Sep
71°
57°

10%

5 h

6 mi/h

Sun, 1 Oct
66°
57°

10%

3 h

5 mi/h

Mon, 2 Oct
64°
57°

10%

5 h

7 mi/h

Accommodations for your vacation in Jamaica Plain

Vacationers who are searching for apartment rental in Jamaica Plain have many alternatives, as they are the most typical accommodation type in this destination. Additionally, the standard size of apartment rental in Jamaica Plain is 102 m² with a median price of $378 a night. Furthermore, if you are going in a group of 4, apartment rental are a great accommodation type in Jamaica Plain, as they usually welcome this exact group size. You can also consider other property types in Jamaica Plain. House rental are, for example, another typical property type in this destination, with 84 offers to compare. The average size of house rental in Jamaica Plain is 78 m², and the average price is $1,039 a night.
What are the best places to discover the arts and culture of Jamaica Plain?

Gardens with history

In addition to major attractions, Boston offers more tranquil places to explore. At Forest Hills Cemetery, you can wander through a stunning sculpture garden and visit the graves of world-famous personalities such as E.E. Cummings, Anne Sexton, and suffragette Alice Stone Blackwell. Don't miss the Firemen's Memorial by celebrated sculptor John Wilson.

Where are the unique attractions in Jamaica Plain?

Relax in the city center's natural habitat

Jamaica Pond forms the center of Jamaica Plain. Part of a thousand-acre string of parks, the spot is a serene environment in which to pass the time. Go boating on the water and grill your catch on the banks as the sun sets. You'll never be far from the culture and conveniences of Boston.

Information about vacation rentals in Jamaica Plain

🏡 Vacation rentals available 1,342 homes
💳 Possible discounts up to 55%
🌙 Nightly prices starting at $99
⭐ Popular amenities Pets allowed, Parking and Internet
🐾 Pet friendly homes 301 homes
🏊 Vacation rentals with pools 384 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Jamaica Plain?

The price of a night's stay in Jamaica Plain starts at $99. If you’re interested in a apartment rental, the average price is $378 per night. A house rental Jamaica Plain will cost on average $1,039 per night.

How many vacation rentals are available for booking in Jamaica Plain?

Currently there are 1,342 rentals to choose from for your upcoming trip.

What amenities are most popular for vacation homes in Jamaica Plain?

Three most popular amenities for home rentals in Jamaica Plain include accommodations that have: Pets allowed, Parking, and Internet.

How many vacation rentals with pools are there in Jamaica Plain?

There are 384 vacation rentals from 5 providers in Jamaica Plain.

Are dogs allowed in vacation rentals in Jamaica Plain?

Finding a rental in Jamaica Plain that allows dogs is definitely possible, with 301 pet-friendly available.

What's the best time to travel to Jamaica Plain?

When looking for a vacation rental in Jamaica Plain, keep in mind that rainy season is typically in December or January, with August often being the driest.

Vacation Destinations Near Jamaica Plain

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