Wine Country Villas - Vacation Rentals in South Brookline

Roslindale village condos From US $674
         

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8.9 (176 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous 5 bedroom Boston Home From US $1,325
         

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New
Villa
  • Air Conditioner
  • Parking
  • Barbecue/Outdoor Cooking

Luxury Places to Stay in South Brookline

Over 449+ Luxury Places to Stay in or Near South Brookline
Sleek Boston Home | Near T From US $1,684
         

New Luxury Renovation | Near T From US $1,467
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Brookline Haven | Rooftop + Deck + Game Room +T From US $1,276
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Gorgeous 5 bed Historic Boston Home From US $1,250
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Beautiful 6000 sq ft home 20 min to Boston From US $1,135
         

9.4 (79 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in South Brookline

Over 50+ Top-Rated Vacation Rentals with a Pool in or Near South Brookline
Brand New Modern Private House in Newton. From US $1,017
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Bright Brighton 1BR w/W/D, Doorman, near T + Shopping, by Blueground From US $170
         

Hilton Garden Inn Boston Brookline, MA From US $155
         

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9.0 (1008 Reviews)
Hotel
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  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $178
         

Courtyard by Marriott Boston Brookline From US $151
         

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8.6 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $307
         

Pet-Friendly Vacation Rentals in South Brookline

Over 175+ Pet-Friendly Vacation Rentals in or Near South Brookline
Modern Townhome - Boston Vacation with 2 Bath, Parking and a Deck From US $390
         

Renovated, Chic, one bed, Sleeps 4,Steps to Transit From US $89
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
182 Heath st From US $163
         

3.6 (4 Reviews)
Apartment
  • Pet Friendly
  • Child Friendly
  • Internet
Newly renovated pet friendly apt by parks and train! From US $210
         

8.0 (36 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bedroom unit with central air in Brookline Village - Near Longwood From US $381
         

Boston vacation,Longwood Medical,mins to MBTA,pkg From US $179
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Budget-Friendly Basement 2BR Retreat From US $198
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in South Brookline

Over 38+ Large Vacation Homes & Villas in or Near South Brookline
City's Hippest Neighborhood. n From US $844
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Boston Single Family House - 19' Train to Back Bay From US $636
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Mid-Century Glam Retreat, Near T From US $438
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern Boston Condo | near T From US $682
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Historic house renovated for modern convenience From US $416
         

9.8 (135 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
88 Boylston Street · Skyrise Two Stories - Centrally Located From US $621
         

9.6 (41 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Boston Renovation | Near T From US $647
         

9.2 (12 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in South Brookline

Over 81+ Wheelchair Accessible Vacation Homes in or Near South Brookline
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

South Brookline Varoom and Airbnb Places to Stay Under $200

Over 160+ South Brookline Varoom 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
A Village Bed and Breakfast From US $151
         

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10.0 (65 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Renovated 1BED, Steps to MBTA, Shops & Restaurants From US $168
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunny,spacious, sleeps 4, steps to MBTA,Hospitals. From US $195
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village From US $200
         

Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $196
         

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

Instantly Bookable Vacation Homes in South Brookline

Over 206+ Instantly Bookable Vacation Homes in or Near South Brookline
Charming Tree Top Victorian - Two Bedroom Retreat From US $404
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxury 3brm/1bath Duplex in JP From US $368
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Arbor Retreat From US $955
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Under the Sun Apartment From US $582
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Modern Condo Walk-Out Basement Near Train From US $286
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Family House with yard at prime location From US $361
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

About South Brookline Vacation Rentals

With more than 2 South Brookline vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Winecountryvillas 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 South Brookline.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Winecountryvillas South 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 South Brookline. Places to stay near South Brookline are 2614.28 ft² on average, with prices averaging $1,000 a night.

Winecountryvillas makes it easy and safe to find and compare vacation rentals in South 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 South Brookline

Type Count
Holiday Apartments 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in South Brookline

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

Weather in South Brookline

View the weather forecast for South Brookline before booking your South 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