Sailings Canada - Vacation Rentals in Brookline

UltraLuxe Apt in Boston Brownstone in Prime Area From US $550
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Walk to Restaurants, Shopping, near BU and Hosp From US $237
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Coolidge Corner Guest House From US $146
         

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8.2 (630 Reviews)
House
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  • Parking
  • TV
Nice 2bd/1.5ba Next to BU 4119 From US $512
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba Next to BU 1183 From US $530
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy 1BR Private Unit w/Patio & Parking From US $469
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Brookline Haven - Rooftop + Deck + Game Room +T From US $1,460
         

10.0 (1 Review)
Apartment
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  • Parking
  • TV
Gorgeous 2BR Next to BU 7731 From US $601
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Luxury Places to Stay in Brookline

Over 313+ Luxury Places to Stay in or Near Brookline
Modern Townhome - Boston Vacation with 2 Bath, Parking and a Deck From US $1,250
         

88 Boylston Street · Skyrise Two Stories - Centrally Located From US $1,044
         

9.6 (42 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bedroom unit with central air in Brookline Village - Near Longwood From US $888
         

Iris Hotel Boston From US $796
         

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8.8 (130 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Brookline

Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Brookline
Hilton Garden Inn Boston Brookline, MA From US $232
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $312
         

Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $375
         

Courtyard by Marriott Boston Brookline From US $277
         

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8.4 (1012 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Boston Brookline, Ma From US $529
         

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8.3 (538 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard by Marriott Boston Brookline From US $385
         

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7.8 (385 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
luxury apt by the lake Boston From US $392
         

New
Apartment
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  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Brookline

Over 74+ Pet-Friendly Vacation Rentals in or Near Brookline
Nice 2bd/1.5ba near BU 3848 From US $529
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Skyrise Two Stories - Centrally Located From US $500
         

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9.2 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
65inTV:Free Parking:Longwood:King Bed:Full Kitchen From US $444
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Brookline Charm 5 min Longwood In-Unit Laundry From US $349
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous 2bd/1.5ba Next to BU 3880 From US $343
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 6369 From US $343
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba near BU 8547 From US $417
         

7.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2BR Next to BU 3774 From US $343
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Brookline

Over 19+ Large Vacation Homes & Villas in or Near Brookline
Furnished Apartment From US $360
         

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8.1 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Hilltop Luxury House 5 Bedrooms and 3.5 Bath From US $449
         

7.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Brookline

Over 101+ Wheelchair Accessible Vacation Homes in or Near Brookline
Walking to Fenway Sunny Perfect Home From US $384
         

9.4 (22 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
A Stylish Stay w/a Queen Bed, Heated Floors. #21 From US $481
         

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8.5 (43 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Iris Hotel Boston From US $295
         

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9.4 (504 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Gorgeous Brookline 1 BR w/Gym, near Shops, by Blueground From US $319
         

Blueground | North Brookline, washer, nr Beacon St From US $247
         

Brookline Vacation Rentals and Airbnb Places to Stay Under $200

Over 68+ Brookline Vacation Rentals and Airbnb Places to Stay Under $200
Cozy 1Bed, 1Bath in Brookline, MBTA From US $132
         

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9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Beacon Inn 1087 From US $122
         

8.0 (804 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bright and spacious fully furnished 1 bedroom From US $194
         

The Arcadian powered by Sonder | Double Bunk Room w/Corridor View From US $196
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Instantly Bookable Vacation Homes in Brookline

Over 131+ Instantly Bookable Vacation Homes in or Near Brookline
UltraLuxe Apt in Boston Brownstone2 in Prime Location From US $679
         

9.8 (79 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Old Brookline Charm 5 minLongwood In-Unit Laundry From US $448
         

2min->Coolidge&GreenT/King Bed/Full Kitchen/Arcade From US $402
         

①min>Coolidge: Full Kitchen- 2 From US $398
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxurious condo in the heart of Coolidge Corner ! From US $359
         

New
House
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  • Bedding/Linens
2 rooms close to Medical From US $307
         

New
House
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  • Security/Safety

About Brookline Vacation Rentals

With more than 322 Brookline vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sailings and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Brookline.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sailings Brookline, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Brookline. Places to stay near Brookline are 528.56 ft² on average, with prices averaging $396 a night.

Sailings makes it easy and safe to find and compare vacation rentals in Brookline with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Brookline

Type Count
Holiday Apartments 188
Vacation Homes 92
Hotels with Suites 33
B&B 1

Use these Quick Filters to Find a Vacation Rental in Brookline

Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Brookline.

Weather in Brookline

View the weather forecast for Brookline before booking your Brookline Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Brookline Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Brookline?

Currently, the total number of properties listed in 2026 is over 322 in the Brookline area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Brookline.