Chicago\92s Best Vacation Rentals - Vacation Rentals in Brookline

Steps to Longwood Medical,MBTA,Boston,shopping,pkg From US $266
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
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 $128
         

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8.2 (626 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Nice 2bd/1.5ba Next to BU 8411 From US $333
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba Next to BU 8519 From US $538
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy 1BR Private Unit w/Patio & Parking From US $290
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Brookline Haven | Rooftop + Deck + Game Room +T From US $1,276
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
65inTV:Free Parking:Longwood:King Bed:Full Kitchen From US $814
         

10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Bedding/Linens

Luxury Places to Stay in Brookline

Over 307+ Luxury Places to Stay in or Near Brookline
Walk To Fenway, Private Home, Perfect Location! From US $1,229
         

9.2 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 3Bed, 2Bath, Near Hospitals & Transports From US $777
         

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8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
3-Bed 2-Bath Brookline Village Townhome w Deck From US $696
         

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7.9 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

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 $155
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $214
         

Courtyard by Marriott Boston Brookline From US $245
         

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8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $375
         

Hilton Garden Inn Boston Brookline, Ma From US $529
         

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8.2 (555 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard by Marriott Boston Brookline From US $385
         

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7.9 (382 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
luxury apt by the lake Boston From US $392
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Brookline

Over 70+ Pet-Friendly Vacation Rentals in or Near Brookline
Nice 2bd/1.5ba near BU 3646 From US $341
         

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
2bd/1.5ba Next to BU 9837 From US $322
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 3748 From US $307
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $215
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sun-filled 1 bed, 1 bath in Brookline Village From US $165
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
88 Boylston Street · Skyrise Two Stories - Centrally Located From US $643
         

9.6 (41 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Brookline Village, Public Transport, Longwood Med From US $273
         

9.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Brookline

Over 17+ Large Vacation Homes & Villas in or Near Brookline
Hilltop Luxury House 5 Bedrooms and 3.5 Bath From US $449
         

7.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Furnished Apartment From US $360
         

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8.1 (38 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

Wheelchair Accessible Vacation Homes in Brookline

Over 105+ Wheelchair Accessible Vacation Homes in or Near Brookline
Walking to Fenway Sunny Perfect Home From US $353
         

9.4 (22 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
A Stylish Stay w/a Queen Bed, Heated Floors. #21 From US $299
         

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8.5 (43 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Iris Hotel Boston From US $218
         

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9.4 (485 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Gorgeous 2bd/1.5ba Next to BU 0773 From US $324
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba near BU 5437 From US $270
         

6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2BR Next to BU 7843 From US $317
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2BR Next to BU 4887 From US $361
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Brookline Vacation Rentals and Airbnb Places to Stay Under $200

Over 86+ 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 $116
         

8.0 (798 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
1BR Close to Longwood Medical From US $179
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous Brookline 1 BR w/Gym, near Shops, by Blueground From US $166
         

Instantly Bookable Vacation Homes in Brookline

Over 137+ Instantly Bookable Vacation Homes in or Near Brookline
UltraLuxe Apt in Boston Brownstone2 in Prime Location From US $518
         

9.8 (79 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Near Public Transport, Fenway, BU, Longwood Med From US $212
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
0.5mile to Boston Children’s, Brigham, Dana F, BI From US $227
         

8.8 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Brookline Charm 5 minLongwood In-Unit Laundry From US $555
         

King Bed 3 min > Washington Sq 1 min >T From US $514
         

Spacious 3Bed, 2Bath, Near Hospitals & Transports From US $508
         

About Brookline Vacation Rentals

With more than 316 Brookline vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals 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 Chicagosbestvacationrentals 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 529.19 ft² on average, with prices averaging $361 a night.

Chicagosbestvacationrentals 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 183
Vacation Homes 90
Hotels with Suites 33
B&B 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Brookline

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals 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

What are the top vacation rentals in Brookline?
How many vacation rentals are available in Brookline?

Currently, the total number of properties listed in 2026 is over 316 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.