The 10 best vacation rentals in Chestnut Hill, US | Booking.com
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Vacation Rentals in Chestnut Hill

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The best vacation rentals in Chestnut Hill

Check out our selection of great vacation rentals in Chestnut Hill

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Newbury Guest House

Boston (Near Chestnut Hill)

This historic guest house is located in Boston's Back Bay district, only 2 minutes' walk from the Hynes Convention Center and various shops along Newbury Street.

D
Deborah
From
United States
This location was excellent. close to food and shops. Highly recommend will stay again when in town. Parking was tricky to get to but very convient behind hotel. Staff was super friendly and accomodating
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 643 reviews
Location 9.8
Price from
$259
1 night, 2 adults
Check availability

Stylish Studio in Historic Boston - Unit #406

Boston (Near Chestnut Hill)

Stylish Studio in Historic Boston - Unit #406 is located in Boston, just 1.5 miles from Massachusetts Institute of Technology and 1.6 miles from Back Bay.

M
Marisa
From
United States
I've stayed here a few times now,and it truly is a great location....Esp close to Fenway Park 🤗🤗
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 23 reviews
Location 9.6
Price from
$133.40
1 night, 2 adults
Check availability

Spacious Medford Gem

Medford (Near Chestnut Hill)

Spacious Medford Gem is located in Medford, just 2.7 miles from Peabody Museum and 2.7 miles from Cambridge College. Both Wifi and private parking are accessible at the apartment free of charge.

M
Mohsen
From
Iran
It was very spacious, super clean and it had everything. The owner was very responsive. The location was very good with available public parking. It has coffee (and decaf), tea, herbal drinks, and even peanut butter for breakfast. All the required utensils and dishes were available. I definitely rate it 10/10.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 27 reviews
Location 9.4
Price from
$268.52
1 night, 2 adults
Check availability

Cozy Get Away Somerville

Somerville (Near Chestnut Hill)

Cozy Get Away Somerville is located in Somerville, just 1.6 miles from Cambridge College and 1.9 miles from Inman Square.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 11 reviews
Location 8.4
Price from
$225
1 night, 2 adults
Check availability

Charming & Stylish Studio on Beacon Hill #6

Boston (Near Chestnut Hill)

Charming & Stylish Studio on Beacon Hill #6 is located in Boston, just a 8-minute walk from TD Garden and 0.8 miles from Old North Church.

H
Heather
From
United States
The building and studio were beautiful. It was comfortable. The location was excellent and very walkable to many places.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 28 reviews
Location 9.7
Price from
$118.45
1 night, 2 adults
Check availability

Oasis Guest House

Boston (Near Chestnut Hill)

Located 5 minutes’ walk from Symphony Hall, this Boston guest house features shared outdoor terraces. Fenway Park, home of the Boston Red Sox, is 1 mile away.

S
Sibilski
From
Poland
Cozy place, real Boston atmosphere
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 1,046 reviews
Location 9.4
Price from
$153
1 night, 2 adults
Check availability

Boston Monadnock Properties

Boston (Near Chestnut Hill)

Featuring a garden, Boston Monadnock Properties features accommodations in Boston.

A
Alex
From
Colombia
It is very clean and organized
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 242 reviews
Location 7.5
Price from
$59.85
1 night, 2 adults
Check availability

Beautiful Victorian house, Room

Boston (Near Chestnut Hill)

Housed in a historic building, Beautiful Victorian house, Room offers accommodations with a terrace and free Wifi in Boston, 2.6 miles from JFK Presidential Library & Museum.

B
Brenda
From
Mexico
Everything was perfect, I felt at home. Moni was always checking on me and on what I needed. I highly recommend this place. It exceeded my expectations.
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 345 reviews
Location 7.9
Price from
$86
1 night, 2 adults
Check availability

The Boston Rental - Multiple Floorplans

Boston (Near Chestnut Hill)

The Boston Rental - Multiple Floorplans offers accommodations in Boston, 1.4 miles from John F. Kennedy Park and 1.8 miles from Brattle Theatre.

A
Andrea
From
Colombia
Ease of check in and check out. Responsive hosts. Clean and tidy space!
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 210 reviews
Location 8.4
Price from
$189
1 night, 2 adults
Check availability

Boston Queen Bedroom

Boston (Near Chestnut Hill)

Boston Queen Bedroom offers accommodations in Boston, 3.5 miles from Back Bay and 3.5 miles from Boston Convention Exhibitors Center.

R
Royce Kamille
From
Philippines
i love how clean and comfortable the room is. kitchen and dining essentials were complete too. the host is really nice and helpful too.
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 305 reviews
Location 7.6
Price from
$128
1 night, 2 adults
Check availability
All vacation rentals in Chestnut Hill

Most booked vacation rentals in Chestnut Hill and surrounding area in the past month

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These vacation rentals in Chestnut Hill and nearby have options with free cancellation

  • Scored out of 10, guest rating 2.0
    Very Poor - What previous guests thought, 2 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #37 offers accommodations in Brookline, 3 miles from Massachusetts Institute of Technology and 3.1 miles from Central Square Theatre.

    From $300.47 per night
  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 9 reviews

    A Stylish Stay with a King Bed and Heated Floors #27 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

    From $300.47 per night
  • Scored out of 10, guest rating 8.4
    Very Good - What previous guests thought, 43 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #36 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 36 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #15 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

  • Modern Studio, quick train to Boston..#16

    Brookline
    Free cancellation options available
    Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 20 reviews

    Modern Studio, quick train to Boston..#16 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

    From $277.74 per night
  • Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 1 review

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #12 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

    From $274.34 per night
  • Scored out of 10, guest rating 6.4
    Pleasant - What previous guests thought, 6 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #3 is located in Brookline, just 1.8 miles from Fenway Park and 2.2 miles from Boston University.

    From $302.15 per night
  • Scored out of 10, guest rating 6.2
    Pleasant - What previous guests thought, 6 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #1 offers accommodations in Brookline, 1.8 miles from Fenway Park and 2.2 miles from Boston University.

Highly rated vacation rentals in Chestnut Hill and nearby

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 27 reviews

    A Stylish Stay w/ a Queen Bed, Heated Floors.. #14 offers accommodations in Brookline, 1.6 miles from Fenway Park and 2 miles from Boston University.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 301 reviews

    Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway provides accommodations within 2.2 miles of the center of Boston, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    From $438 per night
  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 1,046 reviews

    Located 5 minutes’ walk from Symphony Hall, this Boston guest house features shared outdoor terraces. Fenway Park, home of the Boston Red Sox, is 1 mile away.

    From $373.59 per night
  • Scored out of 10, guest rating 8.1
    Very Good - What previous guests thought, 852 reviews

    Located within a 2625 feet radius of Harvard Square and Harvard University, this Cambridge inn offers free WiFi access throughout the property.

    From $259.80 per night
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 643 reviews

    This historic guest house is located in Boston's Back Bay district, only 2 minutes' walk from the Hynes Convention Center and various shops along Newbury Street.

    From $435.66 per night
  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 24 reviews

    233-3 - 4BR Boston - Peaceful Escape near Park Zoo offers accommodations in Boston, 3 miles from JFK Presidential Library & Museum and 3.5 miles from Boston Museum of Fine Arts.

    From $764.88 per night
  • Scored out of 10, guest rating 8.1
    Very Good - What previous guests thought, 39 reviews

    Lovely Two Bedroom Condo in South Boston offers accommodations in Boston, 1.4 miles from Boston Convention Exhibitors Center and 1.5 miles from Boston South Station.

    From $635.02 per night
  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 90 reviews

    Natalie House provides free Wifi and rooms with air conditioning in Boston. The property is around 3 miles from John F. Kennedy Park, 3.4 miles from Brattle Theatre, and 3.6 miles from Central Square.

Enjoy breakfast in Chestnut Hill and nearby

  • Beacon Inn 1750

    Brookline
    Breakfast options
    Scored out of 10, guest rating 6.7
    Pleasant - What previous guests thought, 240 reviews

    This bed and breakfast is in Brookline and is one mile from Boston College. This property is a 19th-century brownstone and features free Wi-Fi in every room.

    From $177 per night

  • Beacon Inn 1087

    Brookline
    Breakfast options
    Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 399 reviews

    This bed and breakfast is located in Brookline and is 3.1 mi from downtown Boston. This 19th century brownstone bed and breakfast offers free Wi-Fi in every room.

    From $223 per night

  • Renovated, Spacious Studio, Near Bc, Bu, Porch is located in Boston, just 3.7 miles from Fenway Park and 4.1 miles from Peabody Museum. The 3-star apartment is 3.6 miles from Brattle Theatre.

  • Sun-filled 1b 1ba W City Views Near Public Trans is located in Boston, just 4.1 miles from Central Square and 4.2 miles from Massachusetts Institute of Technology.

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 3 reviews

    Renovated Studio, Near Hospitals, Mbta is located in Boston, just 2.7 miles from Fenway Park and 3.1 miles from Boston University. This apartment provides air-conditioned accommodations with a patio.

  • Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 4 reviews

    2 Bed, In Unit Laundry, Boston College, Balcony offers accommodations in Boston, 3.1 miles from Boston University and 3.2 miles from John F. Kennedy Park.

  • Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 40 reviews

    Cozy Up in 5BR Apt Near Charming Oak Square features free Wifi and rooms with air conditioning in Boston. The property is around 2.7 miles from John F.

  • Brighton Studio w WD Gym nr T Shops BOS-320 offers accommodations in Boston, 3 miles from Fenway Park and 3.2 miles from John F. Kennedy Park.