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Holiday houses in Dorchester, Boston

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Top-rated holiday rentals in Dorchester, Boston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in Boston

4.89 out of 5 average rating, 251 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.

31 Mar – 7 Apr

$1,733 AUD total

Guest favourite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

19 – 26 Apr

$1,793 AUD total

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

23 Feb – 2 Mar

$1,140 AUD total

Guest favourite

Guest suite in Boston

4.91 out of 5 average rating, 196 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

16 – 23 Oct

$1,415 AUD total

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 265 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

20 – 27 Nov

$1,167 AUD total

Guest favourite

Apartment in Boston

4.97 out of 5 average rating, 217 reviews

Welcoming 2 Bedroom Apt - Close proximity to MBTA

If you're looking to just enjoy all that Boston has to offer or are here to celebrate a graduation, attend a sporting event, milestone birthday or anything else, we promise you this apartment will suit all of your needs. You can access the entire city while feeling cozy and content sipping your coffee or tea on the front porch deck. This second floor walk up is a 4 minute walk to the Forest Hill's Train Station and is minutes from a variety of restaurants and coffee shops.

9 – 16 Nov

$2,268 AUD total

Guest favourite

Apartment in Boston

4.92 out of 5 average rating, 267 reviews

Apartment 1BR mins from JFK/UMASS on Red Line

Airbnb Superhost offering meticulous and specious 1 bedroom 1 bath, sleep sofa and airbed( please request it when booking). Free street parking or in the driveway , free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

24 – 31 Dec

$2,447 AUD total

Guest favourite

Home in Boston

4.89 out of 5 average rating, 296 reviews

Treetop Haven in the City

Our space is unique in that it's completely private, affordable, quiet, clean, and with all the amenities you would find in a regular home. It is also cozy, not fancy, but homey. Think of a place you would find in a relative's home. The deck is special - it looks over our neighbor's backyards with plenty of sun and flowers in the Spring and summer. The neighborhood is quiet and safe. No animals are permitted.

28 Dec – 4 Jan

$1,652 AUD total

Guest favourite

Apartment in Randolph

4.88 out of 5 average rating, 285 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

23 – 30 Jan

$1,571 AUD total

Guest favourite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Before booking, please conduct thorough research on Quincy, MA, to ensure it aligns perfectly with your needs. As a dedicated Superhost, I'm committed to earning your 5-star review. My home offers easy check-in with a keypad entry. The cozy second-floor one-bedroom has a private entrance, spa-like bathroom, well-equipped kitchen, queen-sized bed, 55" TV, high-speed WiFi, and on-site parking for one car.

16 – 23 June

$1,513 AUD total

Guest favourite

Apartment in Quincy

4.95 out of 5 average rating, 238 reviews

Luxury, Location, Privacy. Walk to train. Boston

Luxury. Convenient. Short walk to train. 5 stops to South Station, The main station in Boston. Short walk to stores, restaurants. All brand new. Full gut renovation. Parking spot right outside your private entrance. This is a true getaway. Washer and Dryer also in unit. Beautiful park right across the street

20 – 27 Nov

$2,228 AUD total

Guest favourite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

5 – 12 June

$1,877 AUD total

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Popular amenities for Dorchester, Boston holiday rentals

Free parking on premises

Air conditioning

Stay near Dorchester, Boston's top sights

South Bay Center67 locals recommend

Franklin Park Zoo188 locals recommend

Franklin Park9 locals recommend

Carson Beach73 locals recommend

MATTAPAN SQUARE3 locals recommend

John F. Kennedy Presidential Museum & Library129 locals recommend

Other great holiday rentals in Dorchester, Boston

Guest favourite

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

24 June – 1 July

$1,771 AUD total

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

10 – 17 Mar

$1,764 AUD total

Guest favourite

Guest suite in Newton

4.97 out of 5 average rating, 556 reviews

Spacious suite with private entrance, parking spot

3 – 10 Oct

$1,653 AUD total

Guest suite in Boston

4.83 out of 5 average rating, 182 reviews

New Decor! Cozy Modern Renovated Private Suite!

4 – 11 July

$1,955 AUD total

Home in Boston

4.84 out of 5 average rating, 262 reviews

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

3 – 10 Feb

$1,908 AUD total

Guest favourite

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

24 Sept – 1 Oct

$1,588 AUD total

Guest favourite

Home in Jamaica Plain

4.93 out of 5 average rating, 127 reviews

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

25 Sept – 2 Oct

$2,452 AUD total

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

21 – 28 Dec

$1,577 AUD total

Quick stats about holiday rentals in Dorchester, Boston

Total rentals
940 properties
Wi-Fi availability
930 properties include access to Wi-Fi
Rentals with dedicated workspaces
570 properties have a dedicated workspace
Pet-friendly rentals
140 properties allow pets
Family-friendly rentals
360 properties are a good fit for families
Total number of reviews
40K reviews

Destinations to explore