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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.

Guest favorite

Apartment in Winthrop

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.

Guest favorite

Apartment in Hull

4.95 out of 5 average rating, 66 reviews

Anchors Away Inn Cozy Walk to Beach, Courtyard

A minute walk across the street to your private beach. Walk on picturesque Cadish Ave to Marina and Local 02045. Drive 5 mins to Kenberma shops. A 7 minute drive to main beach restaurants and bars. Comfy Beds and Bamboo linens. Outdoor shower, private backyard with Lg fire pit and large courtyard with string lights and seating. New AC, Fast-Wifi, dedicated workspace. Dining table for 4 plus a Coffee Bar and a snack or two. Comfortable shower with a seat. Pack & play crib, high chair and games.

Guest favorite

Condo in Marblehead

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.

Guest favorite

Apartment in Marblehead

5 out of 5 average rating, 10 reviews

Redtop Retreat in Old Town

Discover this charming condo in the heart of Old Town Marblehead. Gleaming hardwood floors lead to a spacious living room with a decorative fireplace and views of Jeremiah Lee Mansion. The modern kitchen boasts granite counters and modern appliances. Enjoy the large dining room. With two bedrooms, two baths, and a loft, this home offers ample space and off-street parking. Enjoy Abbott Hall, the Public Dock, Crocker Park, shops, and restaurants steps away. Drive 10 minutes to downtown Salem.

Guest favorite

Apartment in Salem

4.98 out of 5 average rating, 374 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.

Guest favorite

Apartment in Swampscott

4.89 out of 5 average rating, 104 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.

Guest favorite

Home in Marblehead

4.91 out of 5 average rating, 44 reviews

Elegant home in historic Marblehead.

Enjoy this spacious, pristine, 4-bedroom home, with lots of light, in historic Marblehead, Massachusetts. It is within walking distance of Marblehead Harbor, Historic District, Devereux Beach, coffee shops, restaurants, boutiques, and other amenities. Open concept first floor. Fully equipped kitchen. 1 king, 1 queen, 1 double bed, and a single. Large baby crib. Two full baths. Laundry facilities. Air Conditioning. Large, private, landscaped yard and plenty of parking. Pet friendly. Edit

Guest favorite

Guest suite in Winthrop

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.

Guest favorite

Apartment in Beverly

5 out of 5 average rating, 21 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!

Superhost

Apartment in Marblehead

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 favorite

Home in Hull

4.95 out of 5 average rating, 21 reviews

Every room a water view updated kitchen & bath

Make some memories at this unique and family-friendly place. 5 minute walk to commuter boat/ferry to Boston, Ma/Logan airport. Ferry ride is 15-30 minutes depending if boat is direct to Boston, MA or stops at Logan or Hingham. Please check ferry schedule as it changes to weekday only in the off season. The house is 28 miles south of Boston. Panoramic water views. Beach access across the street. Vacation or work from home with water views from every window.

Guest favorite

Apartment in Winthrop

4.91 out of 5 average rating, 11 reviews

Charming condo steps from beach

Escape to this recently renovated, 750 sq ft 1-bedroom condo in the heart of Winthrop and half a block from the ocean! With cozy farmhouse decor, modern amenities, and a serene atmosphere, this charming retreat is perfect for a quiet getaway or a relaxing beach vacation. Walkable to nearby restaurants, shops, and easy access to Boston. Ideal for couples or solo travelers looking for a calm, coastal experience.

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

Home in Beverly

4.86 out of 5 average rating, 178 reviews

Beverly Beach House- Upper Deck

Guest favorite

Home in Wakefield

4.92 out of 5 average rating, 12 reviews

60 Jordan-New Construction Townhome

Superhost

Guest suite in Burlington

4.74 out of 5 average rating, 50 reviews

Lovely Two Bedroom Home in Burlington

Superhost

Guest suite in Arlington

4.85 out of 5 average rating, 82 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

Superhost

Home in Framingham

4.85 out of 5 average rating, 80 reviews

Near Boston Beautiful 3 Bedroom in Framingham, MA

Superhost

Home in Greater Mattapan

4.92 out of 5 average rating, 12 reviews

Red Door Oasis

Superhost

Home in East Boston

4.86 out of 5 average rating, 92 reviews

Cozy Oasis: Luxury & Modern Apt By Revere Beach

Superhost

Home in Stoughton

4.54 out of 5 average rating, 13 reviews

Studio Basement Apartment

Show all

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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