Holiday houses in Jamaica Pond

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Top-rated holiday rentals in Jamaica Pond

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Top Guest favourite
A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.
Guest suite in Boston
4.92 out of 5 average rating, 251 reviews

Ann and Esther's Cozy Studio near the Heart of JP

This airy and light private studio is set in a beautiful, secluded backyard/garden. Close to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is microwave, fridge, counter w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

Top Guest favourite
A fully equipped kitchen features a spacious granite countertop with seating for four on elegant black bar stools. Natural light streams in from the nearby window, illuminating the fresh purple flowers arranged as a centerpiece.
Condo in Jamaica Plain
4.91 out of 5 average rating, 287 reviews

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt

Discover serenity in this fully-stocked, 2nd floor unit within a Victorian home in JP. Located on a quiet street near transportation and dining options, it offers access to key destinations like Longwood Medical Area and Downtown Boston. Featuring one bedroom, a cozy living room w/ TV, fully-equipped kitchen, and bathroom, plus a spacious private deck. Rest easy on a plush king-size Tempurpedic bed & a full-sized pullout couch fitting 1 adult or 2 children. Central air for increased comfort.

Guest favourite
The spacious studio features a wooden sleigh bed with a patterned comforter. A cozy seating area includes two modern chairs and a small table near a large window draped with light-colored curtains. An ornate mirror stands against a wall, reflecting the warm wood tones in the room.
Apartment in Brookline
4.84 out of 5 average rating, 123 reviews

1 FREE parking spot - Coolidge Corner-Close to T

Beautiful flat in the heart of Coolidge Corner. Prime location, a few blocks to the T (subway). Very safe & one of the coolest neighborhoods in town. Hop on the T & you'll only be a few stops away from Fenway Park, Kenmore Sq. & Back Bay. Close to Boston Uni., BC, Downtown, Cambridge, John F. Kennedy Birthplace Museum, Coolidge Corner, Longwood Medical Area, supermarkets, restaurants, bars, theater, shops, stores & more! Entire apartment. No shared spaces. 100% private. Parking included.

Top Guest favourite
A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.
Condo in Salem
4.95 out of 5 average rating, 103 reviews

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Top Guest favourite
A spacious living area is highlighted by a large leather sectional sofa adorned with colorful cushions. An upholstered ottoman sits in the center, surrounded by vibrant artworks on the walls. Natural light filters through the windows, illuminating the warm wooden flooring.
Townhouse in Boston
4.95 out of 5 average rating, 115 reviews

Modern JP Townhouse w Parking - quiet & convenient

Hi! Welcome to my beautiful place in the coolest part of Boston! Mine is a well-appointed two-story townhome on a quiet street in fabulous JP. My place has its own off-street parking spot, beautiful windows and light, central heat and air conditioning, and all modern appliances including dishwasher, garbage disposal, gas stove and oven, microwave, and even instant hot water! (Please note that my house is not child-friendly and is available for two people maximum.)

Guest favourite
A compact studio space features a daybed with a colorful blanket and decorative pillows. A small dining table with red chairs is positioned nearby. A floor lamp provides soft light, and a narrow spiral staircase is visible in the background, leading to the upper level.
Apartment in Boston
4.93 out of 5 average rating, 154 reviews

Quirky studio in Jamaica Plain

Private entrance, bath, and kitchen. Located in an 1870 Victorian farmhouse, the studio has two single (twin) beds, for two people maximum. Convenient to T, near the shops and restaurants of JP, 20 min from downtown. PLEASE NOTE the STEEP STAIRS and a NARROW SPIRAL STAIRCASE which may not suit people with mobility or balance issues. (This is part of my larger listing for 4 people, "light and airy separate apartment in JP" with 200+ reviews, 4.9).

Guest favourite
A cozy corner is visible, featuring an upholstered chair beside a vintage table lamp. Two skylights allow natural light to fill the space. A small table holds plants, and colorful rugs create a warm atmosphere while leading to an inviting bedroom beyond.
Guest suite in Boston
4.96 out of 5 average rating, 311 reviews

Private & serene getaway in beautiful JP

Quiet, private & serene walk-up 3rd floor apt. Separate entrance, full bath & kitchenette. Bright and spacious. 3 blocks from the center of JP with great restaurants and shopping. 5 min. walk to the 39 bus to Longwood Area and Back Bay. 15 min. walk to the Orange Line T (subway); 1/2 block from Jamaica Pond. 5 min. walk to the Arboretum. Our space is NOT good for people with large luggage! Tons (truly) of street parking, no permit or restrictions.

Top Guest favourite
An open kitchen area features wooden cabinetry and stainless-steel appliances. A dining table is positioned near a window, while soft lighting highlights the space. The layout connects seamlessly to the living area, offering a cozy view of the sofa in the background.
Apartment in Boston
4.89 out of 5 average rating, 161 reviews

JP Artist Loft Apartment

Take it easy at this unique and tranquil getaway in the Jamaica Plain neighborhood of Boston. Enjoy this entire apartment with sleeping for up to six. Steps away from great Centre Street restaurants, bars, coffee shops, Whole Foods, and Sam Adams brewery! Quick access on the T to exciting downtown Boston, or stay and enjoy peaceful and eclectic JP. Off street parking for 1 car and free street parking year round.

Superhost
A bright living area features light blue walls and exposed beams on the ceiling. A comfortable sofa is positioned near a small dining table with wooden chairs. Two windows are adorned with light curtains, allowing natural light to fill the space.
Apartment in Jamaica Plain, Boston
4.78 out of 5 average rating, 273 reviews

2 BR | 1 BA Close to DWTN & Medical, Free PRKG

Private apartment is located in the Boston neighborhood of Jamaica Plain is only 20 minutes away from the heart of Boston and the Longwood Medical area plus you'll have a place to park your car. There is a full kitchen and access to a shared washer and dryer. It offers privacy for couples, close friends, business travelers, & families. Self check-in anytime after 3 PM or drop your bags earlier if you need.

Top Guest favourite
The exterior of a charming green house is showcased, featuring multiple gabled roofs and a porch with decorative railings. Large windows on the first floor allow ample light, while a balcony extends from the second floor, surrounded by lush trees in warm autumn colors.
Guest suite in Boston
4.96 out of 5 average rating, 216 reviews

Light-filled Private Suite on Beautiful Street

In the heart of hip JPVillage. Peaceful - and private - 3rd floor suite - in our home. This is a great place to be based for visiting Boston: attending conferences, seeing your kids, the various hospital complexes and the sights. Two minute walk to Jamaica Pond and five minute walk to one of Boston's park gems, the Arnold Arboretum. Plenty of Hubway bicycle kiosks as well as bus and "T" access close by.

Guest favourite
An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.
Home in Jamaica Plain, Boston
4.91 out of 5 average rating, 169 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Top Guest favourite
A secluded patio area is visible, featuring a brick pathway and two metal chairs positioned for relaxation. The entrance to the guest unit is framed by a set of steps, accompanied by leafy trees that provide shade and a sense of serenity.
Guest suite in Boston
4.93 out of 5 average rating, 103 reviews

Peaceful Garden Apartment

Your beautiful garden guest unit is a tranquil getaway. The layout is ideal - a bedroom with an ensuite bath; living room with a pull out couch with another full bath; and a kitchen/dining area. Best of all, it's less than a ten minute walk to 500 acres of parkland and "JP" center with great restaurants, pubs, bakeries and shops.

Popular amenities for Jamaica Pond holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Jamaica Pond