Holiday rentals in Brookline

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Top-rated holiday rentals in Brookline

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

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Guest favourite
Flat in Cambridgeport
4.9 out of 5 average rating, 650 reviews

2 BR APT w/ parking near MIT/Harvard/BU/Fenway

STUNNING, RENOVATED 2 BEDROOM APARTMENT! Keyless entry self-checkin, free street parking. Luxurious getaway with 2 queen memory foam beds, 1 full sofa bed, cable TV, WiFi, walk-in shower, fully equipped kitchen with stainless steel appliances, in unit washer/dryer, hardwood & marble flooring throughout, new heating system. Next to MIT, Harvard, BU, Kendall, Boston, Fenway Park, Red & Green lines, Flour Bakery, Whole Foods & Trader Joes. This 1st floor unit is immaculate & professionally cleaned

Top guest favourite
An open concept living area features a plush sectional couch, a large circular coffee table, and a colorful area rug. A wall-mounted 4K UHD Smart TV displays various streaming options. The modern kitchen is visible in the background, showcasing sleek cabinetry and bar seating.
Flat in Brighton
4.96 out of 5 average rating, 54 reviews

Luxury 3BR | Free Parking | Harvard/BU | ROKU TV

Nestled in the charming “Lower Allston” neighborhood of Boston & a 15-minute drive from Downtown Boston, this deluxe 3BR unit boasts an unbeatable location Within minutes you can dine at a myriad of world-class restaurants, explore the prestige of Harvard University, take a stroll along Charles River, and even catch a game at Fenway Park! When you return, a 1300 sq. ft interior awaits, complete with HDTVs in each room, lightning fast 300 Mbps Wi-Fi, and top-of-the-line appliances & furnishings

Guest favourite
Flat in Coolidge Corner
4.83 out of 5 average rating, 115 reviews

1 FREE parking spot - Coolidge Corner-Close to T

Beautiful flat in the heart of Coolidge Corner. Prime location, a few blocks to the T (subway). Very safe & one of the coolest neighborhoods in town. Hop on the T & you'll only be a few stops away from Fenway Park, Kenmore Sq. & Back Bay. Close to Boston Uni., BC, Downtown, Cambridge, John F. Kennedy Birthplace Museum, Coolidge Corner, Longwood Medical Area, supermarkets, restaurants, bars, theater, shops, stores & more! 1 shampoo/conditioner/shower gel/lotion. 1 loofah & 2 toothbrushes inc

Top guest favourite
A small dining area features a round white table with two yellow chairs. A simple floral arrangement sits atop the table. Overhead lighting brightens the space, while a colorful artwork adorns the wall. Bench seating is available along the nearby wall.
Flat in Coolidge Corner
4.96 out of 5 average rating, 53 reviews

A Brookline Sanctuary

You're in the heart of Brookline! LOCAL: Minutes away from a French bakery , Thai restaurant, taqueria, liquor store and small grocery store. More restaurants, cafes and bars down the street in Coolidge Corner and Washington Sq. BOSTON: 5-minute walk to subway stop. 10-min subway ride to Fenway Park. Direct subway to tourist spots! Easy transfer to Cambridge . Perfect for visiting Boston, a friend, a student or colleges. Enjoy the entire floor to yourself with a private entrance!

Guest favourite
A garden-level apartment is situated in a Victorian house, surrounded by well-maintained greenery. The building features unique architectural details, with a porch area visible on the right. Sunlight illuminates the exterior, highlighting a safe and welcoming residential neighborhood.
Flat in Brookline Village
4.89 out of 5 average rating, 35 reviews

A bright garden-level 3-BR apartment in Brookline

This bright garden-level apartment is in a safe neighborhood near Brookline High School. It is at the garden level of an occupied Victorian house, facing a recreational park. It is 100 yards to Brookline Hill T-stop (green D line), close to Longwood Hospitals area. It has three bedrooms, 1.5 bathrooms, and a W/D. This is a smoke-free and pet-free residence. It is best for three adults or a family of 4. Please add $50/night for the fourth adult or fifth child on arrival.

Guest favourite
Flat in Brighton
4.82 out of 5 average rating, 39 reviews

The Finsen: Full Kitchen • City Access • W/D • Gym

Welcome to your new home away from home right by the heart of the city! Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston long term. Additional sleeping arrangements can be provided Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> Fully Stocked Kitchen -> Washer & Dryer -> 1 Queen Bed Ideal for business travelers, couples, nurses, and everyone looking to stay long term in Boston.

Superhost
An elegant Châteauesque building showcases stone architecture adorned with decorative elements. Lush greenery surrounds the entrance, with rounded arches leading to the main door. The steeply pitched roofs and turret-like features contribute to the character of the residence, offering a glimpse of its historic charm.
Apartment in Brookline
4.85 out of 5 average rating, 253 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.

Top guest favourite
Flat in Coolidge Corner
5 out of 5 average rating, 24 reviews

Coolidge Corner-1st Floor-Close to the Subway!

Located just a few blocks from the T (subway). Boston University is right around the corner, and Coolidge Corner, with its cafés, restaurants, theaters, and shops. Hop on the T and you’re only a few stops from Fenway Park, Kenmore Square, and Back Bay. The Longwood Medical Area is also nearby, making it an ideal location for students, professionals, and visitors alike. With supermarkets, coffee shops, pharmacies, and local bars all within walking distance.

Loft in Coolidge Corner
4.78 out of 5 average rating, 192 reviews

Steps to the Green Line & Minutes from Boston! #32

In the heart of Coolidge Corner right off the Green Line, our picturesque studio apartment is a quick train ride to Fenway, Faneuil Hall and the Back Bay. Our space is perfect for solo adventures, business travel, or visiting students at the many neighboring universities. Sleep comfortably on pillow-top mattresses. Other features include heated bathroom floors and shared beautiful stainless steel full kitchens with crafted Italian Granite counter tops.

Top guest favourite
Flat in Coolidge Corner
4.95 out of 5 average rating, 292 reviews

Luxury 2B1B Apt. One Free Parking Spot

Completely renovated 2B1B apartment in the central of Brookline. The full kitchen has everything you need. One king bed in the master bedroom, two full beds in the second bedroom. This is a Garden-level unit with a free parking space. A short walk to T-Stop, restaurants, cafés, groceries and more. About 1 mile to Longwood Medical Area, Fenway and BU. Pets friendly with extra charge $100/pet/Stay. Our places are professionally cleaned & sanitized.

Guest favourite
Flat in Brookline
5 out of 5 average rating, 5 reviews

1400sqft:1 min>T&Washington Sq/Sleeps8/4Bed2Bath

Welcome to your Brookline retreat — a bright, spacious 4-bedroom, 2-bath home designed for comfort, convenience, and group travel. With large windows, warm hardwood floors, modern furnishings, and multiple living spaces, this home is perfect for families, friends, business travelers, and visitors to Boston’s nearby universities and hospitals. Enjoy a fully equipped kitchen, designated dining room, cozy living room, and private balcony.

Superhost
Flat in Brookline
5 out of 5 average rating, 3 reviews

King Bed | 3 min > Washington Sq | 1 min >T

I've hosted & co-hosted for 4 years. All questions are answered here so you can make an informed decision. 🐾 Pet-Friendly Stay! We welcome pets under 20 pounds for a $175 one-time fee. Guests will be responsible for any damages caused by their pets. Experience the peaceful charm just outside of Boston from our cozy 1-bedroom apartment, located on the 3RD FLOOR about 40 steps (please note: NO elevator access).

Popular amenities for Brookline holiday rentals

When is the best time to visit Brookline?

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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 1,800 vacation rentals in North Brookline, over 3,890 vacation rentals in Oak Square, and over 4,570 vacation rentals in Jamaica Plain.

  • Are there vacation rentals with a dedicated workspace in Brookline?

    Yes! Work meets play with ease at over 540 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 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 90 apartment rentals with pools in Brookline, available on Airbnb. Make a splash and soak up the sun in style!

  • 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 private suite rentals in Brookline have wifi?

    Absolutely! We offer over 20 private suite rentals with wifi in Brookline. Enjoy a tailored experience with all the comforts you desire.

  • 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 hotel rentals in Brookline?

    Experience the best of Brookline with our hotel rentals, starting at about $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Brookline?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 190 homes with wifi, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Brookline

  • Total holiday rentals

    Explore 1,080 holiday rentals in Brookline

  • Nightly prices starting at

    Brookline holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 49,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    380 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 240 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wifi availability

    1,060 of Brookline holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ grill across Brookline rentals

  • 4.7 Average rating

    Brookline stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Brookline’s top spots include Jamaica Pond, Reservoir Station and Brookline Village Station

Destinations to explore