Where should I stay in Brookline?

Make yourself at home in Brookline by choosing from our most frequently booked neighborhoods. We have over 1,780 vacation rentals in Chestnut Hill, over 3,660 vacation rentals in Brighton, and over 4,480 vacation rentals in Jamaica Plain.

Are there vacation rentals with a dedicated workspace in Brookline?

Yes! Work meets play with ease at over 510 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 230 vacation rentals for guests traveling with pets.

Do townhouse rentals in Brookline have air conditioning?

Absolutely! We offer over 10 townhouse rentals with air conditioning in Brookline. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Brookline have a bbq area?

Absolutely! We offer over 30 house 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 house rentals in Brookline have wireless internet?

Absolutely! We offer over 210 house 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 apartment rentals in Brookline have a gym?

Absolutely! We offer over 100 apartment rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.

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

Experience the best of Brookline with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Brookline vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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

Rental unit in Winthrop

4.96 out of 5 average rating, 298 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Rental unit in Arlington

4.98 out of 5 average rating, 186 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Superhost

Home in Wayland

4.78 out of 5 average rating, 465 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 162 reviews

Truly Sea-Facing! Boston Gathering Place: ChezGrey

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Guest favorite

Condo in Salem

4.97 out of 5 average rating, 237 reviews

*Historic1710 2Br-Sleeps 7 Halloween|Salem|Parking

Experience spooky fall luxury at The Archer House, Salem’s historic gem! •⁠⁠Elegant 2BR, 2BA apartment with haunted charm •⁠⁠Fast 200mb Wi-Fi, 4K Smart TV for cozy nights •⁠Private workspace for productivity •⁠In-suite washer/dryer for convenience •⁠Fully equipped kitchen with K-cups •⁠Free Level 2 EV charging •⁠10-minute walk to Salem’s fall attractions Your perfect Halloween retreat awaits! ⭐5Star Review This was a perfect location to explore Salem. Super clean, big, and well decorated.

Guest favorite

Rental unit in East Boston

4.97 out of 5 average rating, 131 reviews

Nxt to ocean, 5 min dntwn by T

Embark on an urban escape! Immerse yourself in our chic 2BR/1B + office retreat, ideal for up to 4 guests. Enjoy fast WiFi, steps away from an oceanfront park with stunning Boston skyline views. Walk to the Blue Line T station, one stop to downtown or the airport. Dive into our vibrant, safe historic neighborhood with restaurants, bars, yoga, sailing, and galleries. Not suitable for children, no parking/pets/smoking/cannabis/parties. Make this urban oasis your next unforgettable getaway!

Guest favorite

Guest suite in Winthrop

4.95 out of 5 average rating, 889 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Guest favorite

Condo in East Boston

4.95 out of 5 average rating, 219 reviews

CITY APARTMENT NEAR AIRPORT

🏙️ City Apartment Near Airport Station - New Listing! 🏙️ Experience luxury living in this private one-bedroom apartment, ideally situated just one block from the Airport Station. Enjoy easy access to Boston's vibrant attractions, including: Public Library: Just three blocks away, perfect for a quiet afternoon. Bremen's Park: A beautiful green space for relaxation and outdoor activities. Shopping Centers & Trendy Restaurants: Explore a variety of dining and shopping options nearby.

Guest favorite

Guest suite in Marblehead

4.91 out of 5 average rating, 227 reviews

"Sweet 57" - private entrance suite

Suite with private entrance in quiet family home. Includes kitchenette with a microwave, mini fridge, and coffee maker. Washer/dryer available for week+ long stays (subject to host assistance). Includes access to family room with tv. Ample closet space. Beach chairs, towels, & bikes available. Come for a day or a week. You will not run out of things to do and will find your accommodations private, quiet and safe. NO SMOKING permitted in or anywhere near home.

Superhost

Rental unit in Swampscott

4.85 out of 5 average rating, 196 reviews

Swampscott Oceanside Apartment

Newly remodeled 2 bedroom, 1 bath apartment. ONE block from Fisherman's Beach. Outdoor patio with gas grill, easy parking for 2 cars. Two other beaches within 5-10 minute walk. 10 minutes to Salem and Marblehead, 25-30 minutes to Boston (without traffic). Please see house rules/booking settings for HOLIDAY BOOKING MINIMUMS. We are pet friendly, but require approval prior to booking.

Superhost

Home in Somerville

4.85 out of 5 average rating, 152 reviews

Luciana’s Place

Newly renovated Studio- lower level apartment, with a full bathroom. Queen size bed, one futon for sleeping and lounge seat. Air bed and toddler bed available upon request. Kitchenette (sink, microwave, Ninja air fryer & Keurig), full sized refrigerator with freezer, and a designated dining area with seating for four guests. NO stove top or oven.

Superhost

Rental unit in South End

4.85 out of 5 average rating, 163 reviews

* NEW Listing * A True GEM in South End , Boston!!

Experience Boston at its Best in this true gem apartment in the heart of desirable South End! Best Location! Best Neighborhood! Best bars and restaurants! A guests favorite in the neighborhood, you will fall in love of this charming 1 bedroom apartment with cozy and relaxing private patio in the heart of historical and trendy South End in Boston.

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

Boston University110 locals recommend

Fenway Park815 locals recommend

Boston College69 locals recommend

Massachusetts Institute of Technology (MIT)330 locals recommend

Boston Children's Hospital38 locals recommend

Whole Foods Market1,155 locals recommend

Other great vacation rentals in Brookline

Superhost

Condo in Cambridge

4.89 out of 5 average rating, 135 reviews

#1A-Cambridge Harvard MIT with In unit W/D!

Guest favorite

Rental unit in Medford

4.98 out of 5 average rating, 123 reviews

Couples Retreat - Apt in Charming Colonial Home

Guest favorite

Barn in Nahant

5 out of 5 average rating, 124 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

Superhost

Rental unit in Lynn

4.8 out of 5 average rating, 123 reviews

Beautiful apartment just for you

Guest favorite

Home in Quincy

4.87 out of 5 average rating, 138 reviews

Black Friday! 284 Entire House with huge parking

Guest favorite

Rental unit in Beachmont

4.96 out of 5 average rating, 185 reviews

Ikram's Place Close to Boston,Subway,Airport,Beach

Guest favorite

Guesthouse in West Roxbury

4.95 out of 5 average rating, 191 reviews

Country Cottage in the City

Guest favorite

Guest suite in Arlington

4.85 out of 5 average rating, 79 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

Show all

Quick stats about vacation rentals in Brookline

Total rentals
1K properties
Total number of reviews
42K reviews
Family-friendly rentals
380 properties are a good fit for families
Pet-friendly rentals
230 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace

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 1,780 vacation rentals in Chestnut Hill, over 3,660 vacation rentals in Brighton, and over 4,480 vacation rentals in Jamaica Plain.
Are there vacation rentals with a dedicated workspace in Brookline?
Yes! Work meets play with ease at over 510 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 230 vacation rentals for guests traveling with pets.
Do townhouse rentals in Brookline have air conditioning?
Absolutely! We offer over 10 townhouse rentals with air conditioning in Brookline. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Brookline have a bbq area?
Absolutely! We offer over 30 house 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 house rentals in Brookline have wireless internet?
Absolutely! We offer over 210 house 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 apartment rentals in Brookline have a gym?
Absolutely! We offer over 100 apartment rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Brookline?
Experience the best of Brookline with our house rentals, starting at about $30 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

Rental unit in Winthrop

Rental unit in Arlington

Home in Wayland

Condo in Winthrop

Condo in Salem

Rental unit in East Boston

Guest suite in Winthrop

Condo in East Boston

Guest suite in Marblehead

Rental unit in Swampscott

Home in Somerville

Rental unit in South End

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

Condo in Cambridge

Rental unit in Medford

Barn in Nahant

Rental unit in Lynn

Home in Quincy

Rental unit in Beachmont

Guesthouse in West Roxbury

Guest suite in Arlington

Quick stats about vacation rentals in Brookline

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore