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Holiday homes in Brookline You’ll Love

Top-Rated Brookline Holiday homes for Every Budget and Style!

Looking for a holiday home in Brookline (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $55.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Brookline.

We found 30 Holiday-homes in Brookline and the surrounding area (within 20 miles)

Jacaranda in Milton, USA

Jacaranda

Holiday home in Milton near Brookline, Massachusetts , 342 Blue Hill Avenue
Offering free bikes, Jacaranda provides accommodations in Milton.
  • Parking
  • Family rooms

Very good 21 Reviews 8.2

from $283.83 Show details »

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN in Boston, USA

~*Pet Friendly 30min to Downtown*~ THE B...

Holiday home in Boston near Brookline, Massachusetts , 709 Metropolitan Avenue
~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN offers accommodations in Boston, 6.1 miles from Boston Museum of Fine Arts and 6.9 miles from Fenway ...
  • Parking
  • Pets allowed

Superb 34 Reviews 9.1

from $143.15 Show details »

~*30min to Downtown*~ THE COSMOPOLITAN in Boston, USA

~*30min to Downtown*~ THE COSMOPOLITAN

Holiday home in Boston near Brookline, Massachusetts , 709 Metropolitan Avenue
~*30min to Downtown*~ THE COSMOPOLITAN is located in Boston, just 6.1 miles from Boston Museum of Fine Arts and 6.9 miles from Fenway Park.
  • Parking
  • Family rooms

Fabulous 63 Reviews 8.9

from $148.24 Show details »

Bostons Best Vacation House in Boston, USA

Bostons Best Vacation House

Holiday home in Boston near Brookline, Massachusetts , 61 Temple Street
Bostons Best Vacation House offers accommodations in Boston, 5.3 miles from JFK Presidential Library & Museum and 6 miles from Boston Museum of Fine A...
  • Parking

Very good 1 Reviews 8.0

from $371.36 Show details »

A Little Piece of History in Boston, USA

A Little Piece of History

Holiday home in Boston near Brookline, Massachusetts
A Little Piece of History is located in Boston, just 4.7 miles from Boston South Station and 4.8 miles from Hynes Convention Center.
  • Parking
  • Pets allowed

Superb 27 Reviews 9.1

from $313.04 Show details »

Park-Side Home in Jamaica Plain in Boston, USA

Park-Side Home in Jamaica Plain

Holiday home in Boston near Brookline, Massachusetts , Glen Road 91
Park-Side Home in Jamaica Plain offers accommodations in Boston, 2.7 miles from Boston Museum of Fine Arts and 3.6 miles from Fenway Park.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $348.93 Show details »

Modern Single Family Home minutes from Fort hill in Boston, USA

Modern Single Family Home minutes from F...

Holiday home in Boston near Brookline, Massachusetts , 5 Hilton Terrace
A recently renovated vacation home, Modern Single Family Home minutes from Fort hill offers accommodations in Boston.
  • Parking

Fabulous 20 Reviews 8.7

from $348.41 Show details »

Sun-filled 2br, In-unit Laundry, Near T & Medical in Brookline, USA

Sun-filled 2br, In-unit Laundry, Near T...

Holiday home in Brookline, Massachusetts , 91 Chestnut Street
Sun-filled 2br, In-unit Laundry, Near T & Medical offers accommodations in Brookline, 2.5 miles from Fenway Park and 3 miles from Hynes Convention Cen...

Passable 2 Reviews 5.0

from $97.00 Show details »

Modern Townhome,boston Vacation,2 Bath,pkg,deck in Brookline, USA

Modern Townhome,boston Vacation,2 Bath,p...

Holiday home in Brookline, Massachusetts
Modern Townhome, boston Vacation,2 Bath, pkg,deck is located in Brookline, just 1.7 miles from Boston Museum of Fine Arts and 1.9 miles from Fenway Pa...
  • Pets allowed

Good 6 Reviews 7.9

from $467.46 Show details »

Brookline Village, Central Air, 2b, Near Longwood in Brookline, USA

Brookline Village, Central Air, 2b, Near...

Holiday home in Brookline, Massachusetts , 7 Harvard Square
Brookline Village, Central Air, 2b, Near Longwood is located in Brookline, just 1.7 miles from Boston Museum of Fine Arts and 1.9 miles from Fenway Pa...
  • Pets allowed

Good 3 Reviews 7.3

from $296.24 Show details »

Boston Condominium, First Floor Easy Access To Mb in Boston, USA

Boston Condominium, First Floor Easy Acc...

Holiday home in Boston near Brookline, Massachusetts
Boston Condominium, First Floor Easy Access To Mb is located in Boston, just 3.1 miles from Fenway Park and 3.5 miles from Boston University.
  • Pets allowed

no reviews

from $54.00 Show details »

Renovated, Sunny, Spacious Studio In Boston in Boston, USA

Renovated, Sunny, Spacious Studio In Bos...

Holiday home in Boston near Brookline, Massachusetts
Renovated, Sunny, Spacious Studio In Boston is located in Boston, just 3.1 miles from Fenway Park and 3.5 miles from Boston University.
  • Pets allowed

no reviews

from $53.00 Show details »

Pvt Room, St Marys, Fenway, Longwood, Green Line in Brookline, USA

Pvt Room, St Marys, Fenway, Longwood, Gr...

Holiday home in Brookline, Massachusetts , 1029 Beacon Street
Pvt Room, St Marys, Fenway, Longwood, Green Line is located in Brookline, just a 10-minute walk from Boston University and 1.1 miles from Boston Museu...

Fabulous 16 Reviews 8.7

from $156.75 Show details »

Blueground Fenway 1bd apartment BOS-1110 in Boston, USA

Blueground Fenway 1bd apartment BOS-1110

Holiday home in Boston near Brookline, Massachusetts
Blueground Fenway 1bd apartment BOS-1110 is located in Boston, just a 9-minute walk from Boston University and one mile from Boston Museum of Fine Art...
  • Pets allowed

no reviews

from $75.00 Show details »

Upscale Penthouse w Gym & Parking near MGH & TUFTS in Boston, USA

Upscale Penthouse w Gym & Parking near M...

Holiday home in Boston near Brookline, Massachusetts , 99 Kneeland Street
Just a 12-minute walk from Boston Tea Party Ship & Museum and 0.8 miles from Back Bay, Upscale Penthouse w Gym & Parking near MGH & TUFTS features acc...
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $68.00 Show details »

Beacon Hill: The Aldrich House in Boston, USA

Beacon Hill: The Aldrich House

Holiday home in Boston near Brookline, Massachusetts , 59 Mount Vernon Street
Housed in a historic building, Beacon Hill: The Aldrich House features accommodations with a garden and free Wifi in Boston, a 8-minute walk from King...
  • Pets allowed
  • Bar
  • Family rooms

Exceptional 7 Reviews 9.8

from $72.00 Show details »

Luxe 3BD 2BA apt close to Downtown w Free Parking in Boston, USA

Luxe 3BD 2BA apt close to Downtown w Fre...

Holiday home in Boston near Brookline, Massachusetts , 16R Waverly Street
Luxe 3BD 2BA apt close to Downtown w Free Parking is located in Boston, just 2 miles from Harvard University and 2.2 miles from John F.

no reviews

from $75.00 Show details »

Harvard Squares ONLY Tiny House on the Charles! in Cambridge, USA

Harvard Squares ONLY Tiny House on the C...

Holiday home in Cambridge near Brookline, Massachusetts , 22 Hingham Street
Harvard Squares ONLY Tiny House on the Charles! offers accommodations in Cambridge, 1.6 miles from Massachusetts Institute of Technology and 2.3 miles...

no reviews

from $59.00 Show details »

Private Home Near Kendall Sq - CM-241 in Cambridge, USA

Private Home Near Kendall Sq - CM-241

Holiday home in Cambridge near Brookline, Massachusetts , Cardinal Medeiros Avenue 241
Private Home Near Kendall Sq - CM-241 is located in Cambridge, just 1.6 miles from Peabody Museum and 1.8 miles from Harvard Square.
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 in Cambridge, USA

Luxury Apartment w King Bed Shared Pool...

Holiday home in Cambridge near Brookline, Massachusetts , 151 North First Street
Just 1.1 miles from TD Garden and 1.2 miles from Freedom Trail, Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 features accommodations in Cam...
  • Pets allowed
  • Fitness centre
  • Swimming pool
  • Swimming Pool

no reviews

from $73.00 Show details »

Bright and Pet-Friendly Home 2 Mi to Harvard Square in Watertown, USA

Bright and Pet-Friendly Home 2 Mi to Har...

Holiday home in Watertown near Brookline, Massachusetts
Bright and Pet-Friendly Home 2 Mi to Harvard Square offers accommodations in Watertown, 2.2 miles from Brattle Theatre and 2.2 miles from Harvard Squa...
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $79.00 Show details »

3BR2Bth parking, CambridgeBoston, WD, Subway, AC in Somerville, USA

3BR2Bth parking, CambridgeBoston, WD, Su...

Holiday home in Somerville near Brookline, Massachusetts , 30 Horace Street 2 Floor
3BR2Bth parking, CambridgeBoston, WD, Subway, AC is a recently renovated vacation home in Somerville, near Inman Square.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 14 Reviews 9.6

from $500.77 Show details »

3BR2Bth parking Cambridge Boston in Somerville, USA

3BR2Bth parking Cambridge Boston

Holiday home in Somerville near Brookline, Massachusetts , 30 Horace Street 1 Floor
3BR2Bth parking Cambridge Boston is located in Somerville, just a 14-minute walk from Inman Square and 1.2 miles from Central Square Theatre.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 10 Reviews 9.8

from $254.44 Show details »

Harvard House - 2BR Retreat adjacent to university in Cambridge, USA

Harvard House - 2BR Retreat adjacent to...

Holiday home in Cambridge near Brookline, Massachusetts , 62 Kirkland Street
Harvard House - 2BR Retreat adjacent to university is located in Cambridge, just a 12-minute walk from Harvard University and 0.7 miles from Brattle T...
  • Parking

No reviews yet 1 Reviews 1.0

from $91.00 Show details »

Belmont Home Less Than 3 Mi to Harvard Square! in Belmont, USA

Belmont Home Less Than 3 Mi to Harvard S...

Holiday home in Belmont near Brookline, Massachusetts
Belmont Home Less Than 3 Mi to Harvard Square! is located in Belmont, just 2.7 miles from Brattle Theatre and 2.8 miles from Harvard Square.
  • Parking

Fabulous 8 Reviews 8.8

from $213.87 Show details »

Number of Holiday homes in Brookline 30
Number of guest ratings 6,227
Average price per night $486.00
Lowest price per night $55,00
Highest price per night $3.129,32

Top 10 Cheapest Holiday-homes in Brookline

Discover the Cheapest Holiday-homes in Brookline – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Brookline

Check out the Most Booked Holiday-homes in Brookline – Based on Guest Popularity.

Holiday homes in Brookline (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Brookline can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Brookline for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Brookline should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com