Holiday houses in Jamaica Pond

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Top-rated holiday rentals in Jamaica Pond

Guests agree: these stays are highly rated for location, cleanliness and more.

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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 Jamaica Plain
4.92 out of 5 average rating, 262 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 comfortable living area showcases a navy blue sectional sofa adorned with patterned cushions. A light-colored ottoman sits at the center, accompanied by a traditional area rug. Natural light filters through three striped windows, accentuating the polished hardwood flooring.
Apartment in Jamaica Plain
5.0 out of 5 average rating, 50 reviews

Classic 2 bedroom near Arboretum

2 b'rm apt w. CENTRAL AC in a well-maintained triple decker in unique & diverse Jamaica Plain area of Boston. Spacious, colorful, sunny. Ideal if visiting JP, W. Roxbury, Roslindale or Brookline. Steps from Arboretum, 1 mile from Jamaica Pond, 15-20 min walk (2 min. uber) to subway. Access to shared laundry. Excl. use of front & back decks and shared use of expansive outside patio. 1 queen & 1 full bed. Sorry-No Pets/Smoking. Please inquire before making reservations that include children.

Top Guest favourite
A cozy living room features a dark sofa adorned with decorative pillows, positioned beside a glass coffee table. Light fixtures cast a warm glow, while elegant artwork and a decorative chest add character. Natural light filters in through large windows, enhancing the tranquil ambiance.
Home in Jamaica Plain
4.94 out of 5 average rating, 201 reviews

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

This is a 1st floor private unit nestled in a serene urban enclave. Conveniently surrounded by public transit, shops, and dining options within a 0.6-mile radius. Originally a charming Victorian abode, meticulously renovated in 2016 to seamlessly blend historic elegance with contemporary comforts. Revel in a fully-equipped kitchen, private rear porch, and a tranquil bedroom boasting a plush queen-size bed. Tailored for your short or extended stay needs, with central air for optimal comfort.

Top Guest favourite
An open living space features a cozy futon sofa, small desk, and a television on a side table. A dining table for four is set with plates, while colorful artwork decorates the walls. Windows allow natural light to brighten the room.
Guest suite in Jamaica Plain
4.99 out of 5 average rating, 134 reviews

Printing Press Loft

Your stay is in a former printing company from 1922. Now a ground-floor loft-style home. We're an easy walk to all JP has to offer. The Longwood Medical area. Chinatown, downtown & Cambridge are all a short Uber/Lyft/ subway ride away. The bedroom has a queen-size bed, closet, bureau, bookcase & access to the bathroom. The main area also has bathroom access, a double-size futon sofa/bed. There's a desk, TV & a kitchenette with full-size fridge, microwave, and 2 burner induction cooking.

Guest favourite
Home in Roslindale
5.0 out of 5 average rating, 28 reviews

Boston Buccaneer Retreat

Modern Luxury Near Forest Hills Station – A Sophisticated Urban Retreat Experience unparalleled elegance in this brand-new, high-end residence, perfectly positioned just moments from Forest Hills Station. Designed for discerning travelers, this exquisite home blends sophisticated design, premium finishes, and state-of-the-art amenities. The Orange Line is just outside the porch . save on rental cars and enjoy a gateway to Northeastern University and all of Boston's top transit routes.

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 Jamaica Plain
4.95 out of 5 average rating, 120 reviews

Modern JP Townhouse w Parking - quiet & convenient

Hi! Welcome to my beautiful place in the coolest part of Boston! My home 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 Jamaica Plain
4.93 out of 5 average rating, 160 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 Jamaica Plain
4.96 out of 5 average rating, 320 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.

Superhost
Apartment in Brighton
4.88 out of 5 average rating, 103 reviews

The Weiss : Modern Gallery • Historic Property!

Stay inside a historic restored monastery in Brighton. This spacious studio blends preserved historic architecture with modern comfort and features an expandable room divider for a one-bedroom feel. Just a 5-minute walk to the T with easy access to Boston College, Harvard, hospitals, and downtown Boston. Amenities Include: → Blazing-fast WiFi → 65” Smart TV → Fully stocked kitchen → Washer & dryer → Comfortable queen bed

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 Jamaica Plain
4.89 out of 5 average rating, 173 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.

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 Jamaica Plain
4.94 out of 5 average rating, 118 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 and a door that transforms the living room into a private bedroom; a second 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.

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
4.9 out of 5 average rating, 178 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!

Popular amenities for Jamaica Pond holiday rentals