The 10 best holiday rentals in Boston, USA | Booking.com
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Holiday Rentals in Boston

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Holiday Rentals for every style

Find the right holiday rental for you in Boston

The best holiday rentals in Boston

Check out our pick of great holiday rentals in Boston

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Most booked holiday rentals in Boston and surroundings in the past month

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These holiday rentals in Boston and nearby have options with free cancellation

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

    Offering a shared lounge and city view, A Stylish Stay w/ a Queen Bed, Heated Floors.. #37 is set in Brookline, 2.8 km from Fenway Park and 3.5 km from Boston University.

  • Scored out of 10, guest rating 5.2
    Passable - What previous guests thought, 7 reviews

    Located in Boston, 300 metres from King's Chapel and Burying Ground and less than 1 km from Beacon Hill, Modern Studio In City Center, Near Boston Common offers air conditioning.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 85 reviews

    Offering city views, Charming & Stylish Studio on Beacon Hill #15 is an accommodation located in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 43 reviews

    Offering city views, Charming & Stylish Studio on Beacon Hill #8 is an accommodation located in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 32 reviews

    Offering city views, Charming & Stylish Studio on Beacon Hill #6 is an accommodation situated in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 25 reviews

    Offering city views, Downtown Beacon Hill, Convenient, Comfy Studio #1 is an accommodation located in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 62 reviews

    Offering city views, Downtown Beacon Hill, Convenient, Comfy Studio #14 is an accommodation situated in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 4 reviews

    Offering city views, Comfy Beacon Hill Studio Great for Work Travel #13 is an accommodation situated in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

Highly rated holiday rentals in Boston and nearby

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 18 reviews

    Set in the centre of Boston, 500 metres from Freedom Trail and less than 1 km from Boston South Station, Downtown Studio Apt, Near Grocery And Hospitals offers free WiFi and air conditioning.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 233 reviews

    J Miller Flats by Thatch offers accommodation within 700 metres of the centre of Boston, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

    From US$882.98 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 60 reviews

    Located in Boston, 3.6 km from Boston North Station and 3.6 km from TD Garden, Location+Comfort+Convenience offers air conditioning.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 26 reviews

    Boasting air-conditioned accommodation with a balcony, 2BR Spacious & Comfy 43' Yacht - Heat & AC - On the Freedom Trail - Best Nights Sleep is situated in Boston.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 46 reviews

    Set in Boston, Cozy Downtown Boston Studio, #45 offers city views and free WiFi, 1.9 km from Boston Museum of Fine Arts and 1.8 km from Boston Common.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 23 reviews

    Offering free WiFi and city views, Cozy Downtown Studio, #41 is an accommodation set in Boston, just 1.9 km from Boston Museum of Fine Arts and 1.8 km from Boston Common.

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 63 reviews

    Offering city views, Heart of South End, Convenient, Comfy Studio #42 is an accommodation situated in Boston, 1.9 km from Boston Museum of Fine Arts and 1.8 km from Boston Common.

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 15 reviews

    Offering city views, Stylish Studio in Boston Brownstone, C.Ave #21 is an accommodation located in Boston, 1.9 km from Boston Museum of Fine Arts and 1.8 km from Boston Common.

Enjoy breakfast in Boston and nearby

  • Beacon Inn 1087

    Brookline
    Breakfast options
    Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 401 reviews

    This bed and breakfast is located in Brookline and is 5 km from downtown Boston. This 19th century brownstone bed and breakfast offers free Wi-Fi in every room.

    From US$312 per night

  • Beacon Inn 1750

    Brookline
    Breakfast options
    Scored out of 10, guest rating 6.7
    Pleasant - What previous guests thought, 235 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 US$223 per night
  • Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 60 reviews

    Offering city views, Downtown Beacon Hill, Convenient, Comfy Studio #10 is an accommodation located in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 32 reviews

    Offering city views, Charming & Stylish Studio on Beacon Hill #9 is an accommodation located in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 54 reviews

    Boasting city views, Comfy Beacon Hill Studio Great for Work Travel #7 provides accommodation with a balcony, around 600 metres from Boston Common.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 43 reviews

    Offering city views, Charming & Stylish Studio on Beacon Hill #2 is an accommodation set in Boston, 600 metres from Boston Common and 600 metres from Beacon Hill.

  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 41 reviews

    Located in the centre of Boston, just 500 metres from King's Chapel and Burying Ground and 600 metres from Boston Common, Cozy Furnished Studio in Beacon Hill #4 provides accommodation with city views...

  • Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 228 reviews

    The property is set in Boston, 300 metres from Freedom Trail and 400 metres from Boston Tea Party Ship & Museum.

    From US$424.62 per night

FAQ about holiday rentals in Boston

Holiday rentals that guests love in Boston

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  • Roslindale village condos

    Holiday Rental in Boston
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 167 reviews
    It was very clean and the decorations inside are better than the pictures advertised on the booking app. This property is definitely kin to upscale living and it’s perfect for family getaways. I’m truly impressed. The parking is also readily available; we had 2 vehicles to facilitate our family. I highly recommend this booking to anyone who is seeking a clean, safe neighborhood, and upscale vacation rental.
    Guest review by
    Alejandro
    Family with young children

  • Roslindale village condos

    Holiday Rental in Boston
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 167 reviews
    We were in an apartment on the top floor, very nice and big enough for a family of four, though the single beds could be a little longer, our kids just fitted in them, so it was ok this time and everybody happy. We had a car so the location was great in any direction and no problem to park the car. We took the train downtown once, very easy and the trainstation just a couple of steps away. Would stay there again and will definitely recommend Roslinde Village Condos to those travelin to Boston
    Guest review by
    Johanna Fridur
    Family with young children

  • Roslindale village condos

    Holiday Rental in Boston
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 167 reviews
    The location was good. It's a nice, quiet suburb. Local people were really nice. The accommodation was spacious, cosy and clean. No problems with on street parking. We were warned in advance that some visitors found the noise from the upper floor intrusive. We didn't, we were conscious of people upstairs walking about and of pipes gurgling from time to time, but it wasn't problematic. Traffic in Boston was horrible, so we mostly chose to use the train ($10 to travel all weekend) from Roslindale Village which is a short walk away.
    Guest review by
    John
    Young couple

  • Roslindale village condos

    Holiday Rental in Boston
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 167 reviews
    location was just as expected--short walk to Roslindale Village commuter rail and groceries and restautants.
    Guest review by
    schaper
    Family with young children

  • Quarters on DOT by Thatch

    Holiday Rental in Boston
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 248 reviews
    The description of the property and photos - are 99% match with reality. Haven't had some big expectations from the property, so took it easy - a reasonable place to stay for a short term. Groceries, coffee and bars/restaurants in the area. Ok public connection to the city center, I even walked a couple of times. Responsive staff, even welcomed marathon runners with free fruits and biscuits :)
    Guest review by
    VLADYSLAV
    Group

  • Roslindale village condos

    Holiday Rental in Boston
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 167 reviews
    The Condo was situated in a really quiet area .The Condo was very cozy and cleanliness was second to none. Just a 10 minute walk from Roslindale Village where there were a good selection of nice restaurants and bars to choose from. Plenty of buses go to Forest Hills where you can pick up the T transit system. We are definitely thinking of a return at some point in the future. I would definitely recommend staying there.
    Guest review by
    Paul
    Family with young children