Brookline vacation rentals

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Top-rated vacation rentals in Brookline

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Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 202 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.

Mar 4 – 11

$111 per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 102 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

Mar 12 – 19

$88 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 2 – 9

$94 per night

Superhost

Condo in Brookline

4.84 out of 5 average rating, 112 reviews

Newly renovated Brookline 1bd Apartment

Private, fully updated apartment in the heart of Brookline Village near Longwood Medical Center. Enter through a private entryway. The unit has a full kitchen, dishwasher, oven and a refrigerator. The living room has a couch and tv with cable. Unit includes washer-dryer, wifi, and utilities. Many restaurants/ shops/ grocery minutes from away. Close access to public transportation. We live upstairs with 2 young kids. Guests may hear them around 7am. Brookline Short Term Rental License # 2023-1

Jan 1 – 8

$200 per night

Guest favorite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

Bright "Spotless" studio in single family home. Airbnb and MA COVID cleaning standards are maintained. Ample on street parking. Peaceful family neighborhood minutes from the green line. Near BU, BC, St. E's, Coolidge Corner, Cleveland Circle, Washington Square. 20 minutes from city center. Ideal for professionals, tourists, student, or visiting parents. Hassle free with all basic amenities. "Micro" kitchen (no stove or oven), Central air, heat, WiFi included. Registered and Licensed Airbnb.

Jun 19 – 26

$111 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.

Jun 13 – 20

$144 per night

Guest favorite

Condo in Brookline

4.86 out of 5 average rating, 180 reviews

Luxurious Townhouse Close to Coolidge Corner

This elegant Châteauesque penthouse was originally built circa 1890 and has been gut-renovated to its full grandeur. The kitchen and dining area features oversized windows that flood the space with natural sunlight. The chef’s kitchen is perfect for cooking and entertaining. Four beautiful and spacious bedrooms for guests to rest and relax. One parking space for a compact car is included for guests as well as easy walk to the T and an easy train ride downtown.

Sep 5 – 12

$468 per night

Guest favorite

Apartment in Boston

4.95 out of 5 average rating, 115 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).

Jul 6 – 13

$112 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 12 – 19

$128 per night

Guest favorite

Home in Boston

4.89 out of 5 average rating, 294 reviews

Treetop Haven in the City

Our space is unique in that it's completely private, affordable, quiet, clean, and with all the amenities you would find in a regular home. It is also cozy, not fancy, but homey. Think of a place you would find in a relative's home. The deck is special - it looks over our neighbor's backyards with plenty of sun and flowers in the Spring and summer. The neighborhood is quiet and safe. No animals are permitted.

Dec 25 – Jan 1

$111 per night

Superhost

Guest suite in Boston

4.78 out of 5 average rating, 122 reviews

2 Bedroom guest suite in Brighton w/private bath

Private guest suite in basement level of Victorian house. Includes 2 bedrooms, private living and dining area, private bathroom. Entrance is through kitchen (which you may use) of main house, which features a great porch you are welcome to hang out on. Lots of free on-street parking. Walking distance to Roadrunner concert venue. Host has been vaccinated against Covid-19.

Sep 27 – Oct 4

$103 per night

Guest favorite

Apartment in Boston

4.88 out of 5 average rating, 491 reviews

Serene Studio in a Perfect Location

Our 500 sf 2 room apartment is quiet, private & ideally situated in the heart of Jamaica Plain-just a 4 min. walk to the Orange Line subway and buses. It offers a super comfortable bed, and all the necessities-wifi, 4K smart TV, large eat-in kitchen, Nespresso coffee, and free on-street parking.

Jul 10 – 17

$154 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Brookline vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Brookline's top sights

Jamaica Pond218 locals recommend

Arnold Arboretum of Harvard University379 locals recommend

St. Elizabeth's Medical Center10 locals recommend

Brigham and Women's Hospital21 locals recommend

Boston College69 locals recommend

The Shops at Chestnut Hill56 locals recommend

Other great vacation rentals in Brookline

Guest favorite

Apartment in Boston

4.99 out of 5 average rating, 344 reviews

Executive Garden Apartment

Jun 1 – 8

$212 per night

Guest favorite

Home in Boston

4.93 out of 5 average rating, 272 reviews

All the comforts of home, quiet city neighborhood

$136 per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Dec 3 – 10

$83 per night

Guest favorite

Apartment in Newton

4.96 out of 5 average rating, 381 reviews

Sunny apartment in gracious Victorian

Jul 4 – 11

$144 per night

Guest favorite

Home in Jamaica Plain

4.93 out of 5 average rating, 126 reviews

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

Mar 5 – 12

$157 per night

Guest favorite

Apartment in Newton

4.96 out of 5 average rating, 226 reviews

Convenience Penthouse Suite W/Parking in Newton

Jul 4 – 11

$159 per night

Guest favorite

Loft in Boston

4.93 out of 5 average rating, 196 reviews

Sunny Artist Loft In Historic Brownstone

Aug 24 – 31

$149 per night

Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 196 reviews

Modern and comfortable studio apartment

Nov 3 – 10

$93 per night

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Other great vacation rentals in Brookline

Guest favorite

Apartment in Watertown

4.88 out of 5 average rating, 326 reviews

Private studio close to Boston and Harvard square

Jan 27 – Feb 3

$101 per night

Guest favorite

Apartment in Boston

4.97 out of 5 average rating, 217 reviews

Welcoming 2 Bedroom Apt - Close proximity to MBTA

Nov 5 – 12

$146 per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 170 reviews

Country Cottage in the City

Jun 11 – 18

$127 per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Mar 5 – 12

$130 per night

Superhost

Apartment in Cambridge

4.83 out of 5 average rating, 378 reviews

*1 bedroom * free parking Harvard MIT Cambridge 4

Feb 19 – 26

$109 per night

Guest favorite

Apartment in Newton

4.95 out of 5 average rating, 147 reviews

Sunny, private, comfortable 1 bedroom-convenient.

Sep 30 – Oct 7

$135 per night

Guest favorite

Apartment in Brookline

4.85 out of 5 average rating, 207 reviews

2 Bed Apartment-BU/Fenway/Longwood -free parking!

Jun 30 – Jul 7

$481 per night

Superhost

Apartment in Boston

4.89 out of 5 average rating, 251 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

Mar 11 – 18

$109 per night

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Quick stats about vacation rentals in Brookline

Total rentals
990 properties
Rentals with dedicated workspaces
450 properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
240 properties allow pets
Family-friendly rentals
350 properties are a good fit for families
Total number of reviews
37K reviews

Frequently Asked Questions

Where should I stay in Brookline?
Make yourself at home in Brookline by choosing from our most frequently booked neighborhoods. We have over 4,400 vacation rentals in Jamaica Plain, over 1,740 vacation rentals in Chestnut Hill, and over 3,570 vacation rentals in Brighton.
Do house rentals in Brookline have air conditioning?
Absolutely! We offer over 160 house rentals with air conditioning in Brookline. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Brookline have a bbq area?
Absolutely! We offer over 30 apartment rentals with a bbq area in Brookline. Enjoy a tailored experience with all the comforts you desire.
Are there Brookline apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 apartment rentals with pools in Brookline, available on Airbnb. Make a splash and soak up the sun in style!
Do loft rentals in Brookline have wireless internet?
Absolutely! We offer over 30 loft rentals with wireless internet in Brookline. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Brookline?
Brookline has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do boutique hotel rentals in Brookline have a gym?
Absolutely! We offer over 10 boutique hotel rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.
Are there condo rentals with a dedicated workspace in Brookline?
Yes! Work meets play with ease at over 40 condo rentals in Brookline featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in townhouse rentals in Brookline?
Experience the best of Brookline with our townhouse rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly condo rentals in Brookline?
Four-legged friends are welcome in Brookline. Choose from more than 10 condo rentals for guests traveling with pets.

Brookline vacation rentals

Top-rated vacation rentals in Brookline

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Brookline vacation rentals

Stay near Brookline's top sights

Other great vacation rentals in Brookline

Apartment in Boston

Home in Boston

Guest suite in Watertown

Apartment in Newton

Home in Jamaica Plain

Apartment in Newton

Loft in Boston

Guest suite in Arlington

Other great vacation rentals in Brookline

Apartment in Watertown

Apartment in Boston

Guesthouse in Dedham

Guest suite in Dover

Apartment in Cambridge

Apartment in Newton

Apartment in Brookline

Apartment in Boston

Quick stats about vacation rentals in Brookline

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Brookline?

Do house rentals in Brookline have air conditioning?

Do apartment rentals in Brookline have a bbq area?

Are there Brookline apartment rentals on Airbnb with pools?

Do loft rentals in Brookline have wireless internet?

Are there family-friendly house rentals in Brookline?

Do boutique hotel rentals in Brookline have a gym?

Are there condo rentals with a dedicated workspace in Brookline?

How much does it cost to stay in townhouse rentals in Brookline?

Are there pet-friendly condo rentals in Brookline?

Destinations to explore