Brookline vacation rentals

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Top-rated vacation rentals in Brookline

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

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 110 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

Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 214 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You will love this large 400 sq. ft private 1 bedroom studio. This unit has a private entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

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

Guest favorite

Guest suite in Boston

4.91 out of 5 average rating, 197 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.

Guest favorite

Guest suite in Boston

4.92 out of 5 average rating, 289 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.

Guest favorite

Apartment in Newton

4.91 out of 5 average rating, 270 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.

Guest favorite

Home in Boston

4.89 out of 5 average rating, 297 reviews

Treetop Haven in the City

This is a sweet, cozy space that is not fancy but homey. You will have everything you need for a comfortable stay including a complete kitchen with everything you will need to make your own meals. We are conveniently located, near the subway and buses, supermarkets, restaurants, and coffee shops. We are within two blocks of the jewel of the Emerald Necklace, Jamaica Pond, and other green spaces. Read our reviews so you can see what previous guests have loved about Treetop Haven.

Guest favorite

Apartment in Boston

4.97 out of 5 average rating, 221 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.

Guest favorite

Apartment in Boston

4.95 out of 5 average rating, 118 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 favorite

Guest suite in Brookline

4.88 out of 5 average rating, 188 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.

Guest favorite

Condo in Boston

4.88 out of 5 average rating, 487 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Guest favorite

Apartment in Boston

4.88 out of 5 average rating, 495 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.

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 Newton

4.88 out of 5 average rating, 106 reviews

Newton Decorator's Guest Suite

Guest favorite

Home in Jamaica Plain

4.93 out of 5 average rating, 128 reviews

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

Guest favorite

Apartment in Newton

4.96 out of 5 average rating, 230 reviews

Convenience Penthouse Suite W/Parking in Newton

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 269 reviews

Private 1BR Pied-a-terre

Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 200 reviews

Modern and comfortable studio apartment

Guest favorite

Guest suite in Dover

4.97 out of 5 average rating, 189 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Guest favorite

Apartment in Watertown

4.98 out of 5 average rating, 207 reviews

NEW Modern Apartment Near Boston & Harvard Square.

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

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Other great vacation rentals in Brookline

Guest favorite

Apartment in Watertown

4.88 out of 5 average rating, 336 reviews

Private studio close to Boston and Harvard square

Guest favorite

Apartment in Newton

4.96 out of 5 average rating, 387 reviews

Sunny apartment in gracious Victorian

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 206 reviews

Private guest house on beautiful country road

Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 204 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

Guest favorite

Apartment in Boston

4.91 out of 5 average rating, 149 reviews

Artistic charm in hip J.P.

Guest favorite

Apartment in Newton

4.95 out of 5 average rating, 149 reviews

Sunny, private, comfortable 1 bedroom-convenient.

Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 181 reviews

Light-filled Private Suite on Beautiful Street

Guest favorite

Home in Dedham

4.85 out of 5 average rating, 492 reviews

Private apartment close the city!

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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.
Are there vacation rentals with a dedicated workspace in Brookline?
Yes! Work meets play with ease at over 450 vacation rentals in Brookline featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Brookline?
Four-legged friends are welcome in Brookline. Choose from more than 240 vacation rentals for guests traveling with pets.
Do hotel rentals in Brookline have air conditioning?
Absolutely! We offer over 10 hotel 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 hotel rentals in Brookline have wireless internet?
Absolutely! We offer over 10 hotel rentals with wireless internet in Brookline. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly bed and breakfast rentals in Brookline?
Brookline has more than 10 family-friendly bed and breakfast rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in Brookline have a gym?
Absolutely! We offer over 10 hotel rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in private suite rentals in Brookline?
Experience the best of Brookline with our private suite rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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 Newton

Home in Jamaica Plain

Apartment in Newton

Guest suite in Watertown

Guest suite in Arlington

Guest suite in Dover

Apartment in Watertown

Guest suite in Peabody

Other great vacation rentals in Brookline

Apartment in Watertown

Apartment in Newton

Guesthouse in Framingham

Guest suite in Boston

Apartment in Boston

Apartment in Newton

Guest suite in Boston

Home in Dedham

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?

Are there vacation rentals with a dedicated workspace in Brookline?

Are there pet-friendly vacation rentals in Brookline?

Do hotel 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 hotel rentals in Brookline have wireless internet?

Are there family-friendly bed and breakfast rentals in Brookline?

Do hotel rentals in Brookline have a gym?

How much does it cost to stay in private suite rentals in Brookline?

Destinations to explore