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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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Apartment

4.96 out of 5 average rating, 301 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.

Apartment

4.8 out of 5 average rating, 5 reviews

Located in the heart of S.Boston

Everything you need and more in private condo. located in the heart of South Boston. Professionally cleaned before every stay. King bed. So much to do in the area in any Season. Updated kitchen (granite, full size appliances including DW), W&D in basement. Less than .5 miles from West Broadway T (Red Line). Walkable to over 20 restaurants. Walkable to the beach. .5 miles from Seaport and Convention Center. Open street parking. Quintessential Boston Condo. Five star reviews on all my rentals

Condo

4.99 out of 5 average rating, 171 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

Apartment

4.98 out of 5 average rating, 373 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Apartment

4.89 out of 5 average rating, 103 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Condo

4.97 out of 5 average rating, 245 reviews

*Historic1710 Home Sleeps 7|DownTownSalem+Parking

This elegant 2-bedroom apartment, designed by the homme team, is a perfect retreat for those exploring Salem's haunted history and magical charm. The Archer House blends modern comforts with easy access to Salem’s top attractions, restaurants, and bars ideal for family or friend travelers. Immerse yourself in the area's mystique with iconic sites just steps away! 🕸 Hocus Pocus House - 5 min walk 🧙🏻‍♀️ Witch Museum - 5 min walk 🎃 Witch House - 10 min walk See below to discover more!

Apartment

4.97 out of 5 average rating, 139 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 suite

4.95 out of 5 average rating, 897 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.

Apartment

5 out of 5 average rating, 20 reviews

#1 Top Flr Waterview|Lux Design|Pvt Balcony

Experience luxury in this top-floor apartment with stunning water views. Enjoy air conditioning, a private balcony, plush linens, and a custom desk with wireless monitor. Free off-street parking included. Centrally located, you're steps from restaurants and a short walk to the train station for easy access to Boston. Perfect for a serene getaway or productive stay, with Salem's historic charm just minutes away. Book now for a blend of comfort, convenience, and coastal beauty!

Apartment

5 out of 5 average rating, 3 reviews

Captains Qs 2 bed, downtown MHD sleeps 4, parking

‘Captain’s Quarters’ New! In the heart of Historic Old Town Marblehead. Situated close to Maddies, the Landing, shopping and right next to the Driftwood diner, for the best breakfasts and fried dough on the weekends! Steps to the harbor where you can easily access local yacht clubs and a Public launch service is available for Harbour tours. Prime parking, AC, a fresh modern clean space and amenities will provide you with a very relaxing stay in our beautiful seaside town

Guest suite

4.91 out of 5 average rating, 228 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.

Home

4.86 out of 5 average rating, 178 reviews

Beverly Beach House- Upper Deck

Half block from the beach in the scenic North Shore. Get away from it all in this beach bungalow. Close to downtown restaurants and shops, Historic Cabot theater and more. Large historic colonial home with 3 bedrooms and 2 bath with ocean views and off street parking. Large deck and full kitchen. 30 min train to Boston. Easy quick access to popular destinations such as Marblehead, Rockport, Newburyport, Gloucester and more.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

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Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Brookline vacation rentals

Laptop-friendly workspace

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

Home

4.75 out of 5 average rating, 166 reviews

Walk to Everything Great about Marblehead!

Home

4.92 out of 5 average rating, 12 reviews

60 Jordan-New Construction Townhome

Guest suite

4.74 out of 5 average rating, 50 reviews

Lovely Two Bedroom Home in Burlington

Apartment

4.98 out of 5 average rating, 126 reviews

Couples Retreat - Apt in Charming Colonial Home

Apartment

4.94 out of 5 average rating, 303 reviews

North shore getaway! Near Salem ,Gloucester

Home

4.96 out of 5 average rating, 25 reviews

Master Suite with magnificent views of the ocean

Apartment

4.75 out of 5 average rating, 297 reviews

Salem/Beverly-Now booking for all of 2025!

Apartment

4.99 out of 5 average rating, 74 reviews

New 3 bedroom, 2 bath unit, meadow view!

Quick stats about vacation rentals in Brookline

Total rentals
1K properties
Total number of reviews
44K reviews
Family-friendly rentals
380 properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
520 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 1,770 vacation rentals in Chestnut Hill, over 3,740 vacation rentals in Brighton, and over 4,470 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 bed and breakfast rentals in Brookline have air conditioning?
Absolutely! We offer over 30 bed and breakfast 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 boutique hotel rentals in Brookline have wireless internet?
Absolutely! We offer over 20 boutique 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 condo rentals in Brookline have a gym?
Absolutely! We offer over 10 condo rentals with a gym in Brookline. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Brookline?
Experience the best of Brookline with our condo rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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