Vacation rentals with outdoor seating in Brookline

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Top-rated outdoor seating rentals in Brookline

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Jan 14 – 21

G$21,002 GYD per night

Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Jan 24 – 31

G$26,759 GYD per night

Superhost

Apartment in Boston

4.89 out of 5 average rating, 251 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.

Feb 24 – Mar 3

G$25,477 GYD per night

Guest favorite

Guest suite in Boston

4.91 out of 5 average rating, 196 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk 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 a microwave, fridge, counter and and sink but no stove or cooking options.

Oct 13 – 20

G$22,474 GYD per night

Guest favorite

Home in Boston

4.93 out of 5 average rating, 272 reviews

All the comforts of home, quiet city neighborhood

Sleep peacefully in this beautiful home above Oak Square>Brighton>Boston. Updated, comfortably furnished, well-stocked with electronics, appliances, and housewares. Driveway parking spot. Ideal for couples, solo adventurers, and business travelers with auto or use ride services. Laundry service one mile away. Newbury Street: 8 miles away, North End: 9 miles, Seaport: 9 miles, Logan airport: 11 miles. Close to BC/Harvard; 1 mile from I-90/Mass Pike in Newton Corner, restaurants, attractions.

Jul 17 – 24

G$33,816 GYD per night

Guest favorite

Apartment in Newton

4.95 out of 5 average rating, 147 reviews

Sunny, private, comfortable 1 bedroom-convenient.

This listing features a sunny great room. The great room has a large, comfortable couch, TV and desk. Highlights include a modern kitchenette, a new bathroom and air mattress available upon request. The bed is FULL size. You'll have a private stairway that leads to your private entrance. Nice view for sunsets. You have a dedicated parking space. The apartment is in Newton Upper Falls. Close to Mass Pike, route 128 and route 9. It is a 15 minute walk to the Green Line -D route-Eliot Stop

Dec 20 – 27

G$32,260 GYD per night

Guest favorite

Apartment in Newton

4.91 out of 5 average rating, 265 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, and public transportation. Easy to take in all the Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or sit on the patio and enjoy the outdoors. Come and go as you please with a private entry. Great for quick visits or extended stays. Please note: Construction next door can be loud during the day.

Oct 10 – 17

G$34,400 GYD per night

Guest favorite

Home in Jamaica Plain

4.93 out of 5 average rating, 127 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.

Nov 5 – 12

G$37,800 GYD per night

Guest favorite

Apartment in Boston

4.98 out of 5 average rating, 251 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); ten minutes to Back Bay Station on the T. 1/2 block from Jamaica Pond. 5 min. walk to the Arboretum. Our space is NOT good for people with huge luggage! Tons (truly) of street parking, no permit or restrictions.

Jul 2 – 9

G$44,917 GYD per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Sep 18 – 25

G$31,144 GYD per night

Guest favorite

Apartment in Boston

4.97 out of 5 average rating, 217 reviews

Welcoming 2 Bedroom Apt - Close proximity to MBTA

If you're looking to just enjoy all that Boston has to offer or are here to celebrate a graduation, attend a sporting event, milestone birthday or anything else, we promise you this apartment will suit all of your needs. You can access the entire city while feeling cozy and content sipping your coffee or tea on the front porch deck. This second floor walk up is a 4 minute walk to the Forest Hill's Train Station and is minutes from a variety of restaurants and coffee shops.

Nov 8 – 15

G$35,054 GYD per night

Guest favorite

Guest suite in Brookline

4.87 out of 5 average rating, 183 reviews

Brookline Home with a Garden

Our home is located in a peaceful neighborhood in South Brookline (Chestnut Hill), and is 5 miles from the city of Boston (about a 15 minute drive). The nearest MBTA train stop (the orange line) is about a 5 minute drive from our home. The 1 bedroom apartment is in the basement of our single family home. It is equipped with its own entrance, bathroom, kitchenette, porch, and garden. The apartment has space for up to 3 guests.

Aug 11 – 18

G$30,668 GYD per night