Brookline, Massachusetts

Vacation Rentals in Brookline, Massachusetts

Discover 57 vacation rental properties in Brookline. From 1 to 5 bedrooms. Average $291/night. 100% have pools.

57 verified listings Book securely on VRBO Prices updated March 2026

57 properties available

Renovated,steps to T,Longwood Med

Renovated,steps to T,Longwood Med

2 beds 1 bath
PoolA/CWiFiBalcony
$347/night
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Large private room 10min walk to Fenway,BC,BU,T

Large private room 10min walk to Fenway,BC,BU,T

1 bed 1 bath
PoolA/CWiFiBalcony
$137/night
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A bright studio apartment with private entrance near C&D trains to Boston

A bright studio apartment with private entrance near C&D trains to Boston

1 bath
PoolA/CWiFiBalcony
$142/night
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Renovated Studio, near hospitals, MBTA

Renovated Studio, near hospitals, MBTA

1 bath
PoolA/CWiFiBalcony
$146/night
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Cozy 1Bed, 1Bath in Brookline, MBTA

Cozy 1Bed, 1Bath in Brookline, MBTA

1 bed 1 bath
PoolA/CWiFiBalcony
$122/night
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Sunny private room,Longwood, 10min walk to Fenway

Sunny private room,Longwood, 10min walk to Fenway

1 bed 1 bath
PoolA/CWiFiBalcony
$192/night
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Longwood Medical Condominium

Longwood Medical Condominium

1 bed 1 bath
PoolA/CWiFiBalcony
$207/night
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Walking to Fenway Sunny Perfect Home

Walking to Fenway Sunny Perfect Home

1 bed
PoolA/CWiFiBalcony
$281/night
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Gut Renovated 1-Bed Close to Longwood & MBTA

Gut Renovated 1-Bed Close to Longwood & MBTA

1 bed 1 bath
PoolA/CWiFiBalcony
$183/night
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The Arcadian powered by Sonder | Double Queen Room w/ Corridor View

The Arcadian powered by Sonder | Double Queen Room w/ Corridor View

1 bath
PoolA/CWiFiBalcony
$316/night
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Washington Square condo near trains, Boston College

Washington Square condo near trains, Boston College

1 bed 1 bath
PoolA/CWiFiBalcony
$116/night
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"Home Away from Home" is in a Victorian home in a beautiful, safe neighborhood

"Home Away from Home" is in a Victorian home in a beautiful, safe neighborhood

2 beds 1 bath
PoolA/CWiFiBalcony
$90/night
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Coolidge Corner,steps to C line,Longwood Medical

Coolidge Corner,steps to C line,Longwood Medical

1 bath
PoolA/CWiFiBalcony
$164/night
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Great 1 bed close to Longwd Med, Fenway, parkng

Great 1 bed close to Longwd Med, Fenway, parkng

1 bed 1 bath
PoolA/CWiFiBalcony
$235/night
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The Arcadian powered by Sonder | Double Full Room w/ Corridor View

The Arcadian powered by Sonder | Double Full Room w/ Corridor View

1 bath
PoolA/CWiFiBalcony
$305/night
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Furnished First-Floor Studio in Coolidge Corner

Furnished First-Floor Studio in Coolidge Corner

1 bath
PoolA/CWiFiBalcony
$119/night
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Renovated 1BED, Steps to MBTA, Shops & Restaurants

Renovated 1BED, Steps to MBTA, Shops & Restaurants

1 bed 1 bath
PoolA/CWiFiBalcony
$202/night
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Sunny,spacious, sleeps 4, steps to MBTA,Hospitals.

Sunny,spacious, sleeps 4, steps to MBTA,Hospitals.

1 bed 1 bath
PoolA/CWiFiBalcony
$197/night
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Unit2 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS

Unit2 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS

2 beds 1 bath
PoolA/CWiFiBalcony
$221/night
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The Arcadian powered by Sonder | Queen Room w/ Corridor View

The Arcadian powered by Sonder | Queen Room w/ Corridor View

1 bath
PoolA/CWiFiBalcony
$253/night
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Sun-filled Newly Renovated 1Bed, MBTA

Sun-filled Newly Renovated 1Bed, MBTA

1 bed 1 bath
PoolA/CWiFiBalcony
$197/night
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Spacious 1BR steps from Cooldige Corner in Brookline, by Blueground

Spacious 1BR steps from Cooldige Corner in Brookline, by Blueground

1 bed 1 bath
PoolA/CWiFiBalcony
$149/night
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Spacious 1Bed close to Longwood Medical, Boston

Spacious 1Bed close to Longwood Medical, Boston

1 bed 1 bath
PoolA/CWiFiBalcony
$152/night
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Fully Furnished Spacious Coolidge Corner Studio

Fully Furnished Spacious Coolidge Corner Studio

1 bath
PoolA/CWiFiBalcony
$126/night
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The Arcadian powered by Sonder | Double Full Room w/ Street View

The Arcadian powered by Sonder | Double Full Room w/ Street View

1 bath
PoolA/CWiFiBalcony
$305/night
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Steps to Longwood Medical,MBTA,Boston,shopping,pkg

Steps to Longwood Medical,MBTA,Boston,shopping,pkg

2 beds 1 bath
PoolA/CWiFiBalcony
$324/night
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Newly Renovated, 2Bed Steps to Longwood Med Center

Newly Renovated, 2Bed Steps to Longwood Med Center

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Fully Furnished 1Bed Steps to Longwood Medical

Fully Furnished 1Bed Steps to Longwood Medical

1 bed 1 bath
PoolA/CWiFiBalcony
$264/night
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CDCcleaning, Modern, Private, 1 Bdrm

CDCcleaning, Modern, Private, 1 Bdrm

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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The Arcadian powered by Sonder | Superior King Room w/ Street View

The Arcadian powered by Sonder | Superior King Room w/ Street View

1 bath
PoolA/CWiFiBalcony
$343/night
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The Arcadian powered by Sonder | King Room w/ Corridor View

The Arcadian powered by Sonder | King Room w/ Corridor View

1 bath
PoolA/CWiFiBalcony
$257/night
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Modern townhome,Boston vacation,2 bath,pkg,deck

Modern townhome,Boston vacation,2 bath,pkg,deck

3 beds 2 baths
PoolA/CWiFiBalcony
$470/night
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88 Boylston Street · Skyrise Two Stories - Centrally Located

88 Boylston Street · Skyrise Two Stories - Centrally Located

4 beds 2 baths
PoolA/CWiFiBalcony
$624/night
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Hilltop Luxury House 5 Bedrooms and 3.5 Bath

Hilltop Luxury House 5 Bedrooms and 3.5 Bath

5 beds 4 baths
PoolA/CWiFiBalcony
$757/night
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Huge,3 bed,2bath,Public transport,Boston,sleeps 9

Huge,3 bed,2bath,Public transport,Boston,sleeps 9

3 beds 2 baths
PoolA/CWiFiBalcony
$474/night
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Boston vacation,Longwood Medical,mins to MBTA,pkg

Boston vacation,Longwood Medical,mins to MBTA,pkg

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
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Whole House Loft w/Peloton

Whole House Loft w/Peloton

4 beds 3 baths
PoolA/CWiFiBalcony
$653/night
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The Arcadian powered by Sonder | Superior King Room

The Arcadian powered by Sonder | Superior King Room

1 bath
PoolA/CWiFiBalcony
$368/night
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The Arcadian powered by Sonder | Spacious King Room w/ Street View

The Arcadian powered by Sonder | Spacious King Room w/ Street View

1 bed 1 bath
PoolA/CWiFiBalcony
$357/night
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Renovated 1Bed, Steps to Coolidge Cor Shops, etc

Renovated 1Bed, Steps to Coolidge Cor Shops, etc

1 bed 1 bath
PoolA/CWiFiBalcony
$168/night
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Beautiful Luxury 3br / 2ba Parking in Boston Brookline Exceptional Location!

Beautiful Luxury 3br / 2ba Parking in Boston Brookline Exceptional Location!

3 beds 2 baths
PoolA/CWiFiBalcony
$290/night
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The Arcadian powered by Sonder | Double Bunk Room w/ Corridor View

The Arcadian powered by Sonder | Double Bunk Room w/ Corridor View

1 bath
PoolA/CWiFiBalcony
$334/night
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The Arcadian powered by Sonder | Accessible Double Full Room w/ Street View

The Arcadian powered by Sonder | Accessible Double Full Room w/ Street View

1 bath
PoolA/CWiFiBalcony
$361/night
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Near Longwood, Transit, Parking - Newly Renovated!

Near Longwood, Transit, Parking - Newly Renovated!

1 bed 1 bath
PoolA/CWiFiBalcony
$328/night
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The Arcadian powered by Sonder | Accessible King Room

The Arcadian powered by Sonder | Accessible King Room

1 bath
PoolA/CWiFiBalcony
$418/night
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Renovated Studio at a 10min walk to Fenway, T

Renovated Studio at a 10min walk to Fenway, T

1 bath
PoolA/CWiFiBalcony
$231/night
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Spacious 4BR 2BTH Apt near NU

Spacious 4BR 2BTH Apt near NU

4 beds 1 bath
PoolA/CWiFiBalcony
$331/night
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2 Bdrm in Brookline Village

2 Bdrm in Brookline Village

2 beds 1 bath
PoolA/CWiFiBalcony
$183/night
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More destinations in Massachusetts

Boston (1034) Nantucket (637) Provincetown (428) Falmouth (348) Wellfleet (288) Cambridge (276) Brewster (271) Chatham (258) Plymouth (247) Gloucester (203) Yarmouth (164) Sandwich (163) Rockport (158) Barnstable (155) Eastham (143) Dennis (139) Dennis Port (129) North Truro (126) Hyannis (121) South Yarmouth (115)