Vacation rentals in Dorchester

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Top-rated vacation rentals in Dorchester

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

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Top guest favorite
Guest suite in Boston
4.9 out of 5 average rating, 181 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Top guest favorite
Guest suite in Ashmont
4.96 out of 5 average rating, 275 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Superhost
Home in Dorchester
4.9 out of 5 average rating, 153 reviews

New Spacious Home in Boston

Welcome to our spacious urban retreat in the heart of Boston. This well maintained 4 bedroom unit is conveniently located near many city attractions. Enjoy quiet patio, backyard and free coffee bar. Great for a quick getaway or special gathering. 5 min walk to access bus and train 10 min drive to UMass Boston and JFK Library 20 min drive to Fenway Park and TD garden sports 10 min drive to the famous Franklin Park Zoo/Golf Course 20 min drive to Historical Downtown Boston and Prudential Shopping

Top guest favorite
The kitchen features a combination of modern and rustic elements, with dark cabinetry contrasting against exposed brick walls. A spacious island with a countertop is complemented by three metal stools. Task lighting illuminates the space, highlighting an efficient layout with ample storage.
Apartment in Allston
5 out of 5 average rating, 122 reviews

Brookline - Mod Apartment in Classic Neighborhood

So convenient! Walk to Boston U., Coolidge Crnr, Fenway Park and Allston Village for shopping, restaurants, entertainment. Just 3 miles from downtown. 2 blocks from MBTA Station-easy commute to Longwood Med Ctr, Harvard, MIT, Boston College, the Financial District and more. Beautiful, spacious, newly renovated one bedroom apartment – open floor plan, fabulous kitchen and spa bathroom. Designer furnishings throughout and fully equipped. Ideal for the long term biz traveler or couples on holiday.

Top guest favorite
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Apartment in Nahant
4.94 out of 5 average rating, 163 reviews

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

Top guest favorite
A three-story yellow Victorian house is shown, featuring elegant architectural details such as a central entryway with a rounded arch and large balcony. Windows adorned with black shutters frame the façade, while colorful flowers and shrubs decorate the front yard.
Apartment in Dorchester
4.89 out of 5 average rating, 683 reviews

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

Guest favorite
An outdoor patio is illuminated by string lights, showcasing an inviting seating area with multiple chairs and lounge furniture arranged around a central rug. A large umbrella provides shade over a bar area, surrounded by greenery and a bright evening sky.
Apartment in Ashmont
4.84 out of 5 average rating, 263 reviews

🎖The Ashmont Apartment | Close to Subway/Downtown

This unique 2 bed/2 bath apartment is brand new, along with all the furnishings and amenities. The unit includes 1 Queen + 1 Full size en-suite bedrooms. The unit is extremely clean and beautifully decorated. Only a 5 minute walk to Ashmont T station (red line), which takes you directly into Downtown Boston, Harvard, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Guest favorite
Apartment in Brighton
4.96 out of 5 average rating, 144 reviews

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Guest favorite
Home in Dorchester
4.96 out of 5 average rating, 137 reviews

LargeDuplex10Beds w/prkg near Downton

Blending modern conveniences with historic charm, this newly renovated duplex features 5 bedrooms/2 bathrooms. Open space kitchen-living room, 55"Roku TV. Free Wifi. Free Laundry 8mns to Beach Free Street Parking 4.6 miles to Downtown, Convention. Perfect for large groups Close to major Universities. 8 Minutes walk to train Free coffee/tea, toaster, blender. Free linens, towels. 10 mns to Dorchester brewing, South Bay center & beach. We love and look forward to hosting you.

Guest favorite
Apartment in South End
4.86 out of 5 average rating, 154 reviews

The Upton - The Upton Boston, South End

See more photos at our IG @theuptonboston The Upton was designed to be the ideal home base. Staying here means you are next to restaurants, shopping, site-seeing, & visiting family in the South End. Ideal for business travel or tourism. Our guests choose us for our historic charm and perfect location. The Upton features 2 dining (or work) spaces with expansive Victorian windows giving way to views of Tremont Street & a leafy, calm side street. We look forward to hosting you.

Top guest favorite
The exterior of a three-story building is presented, featuring a light blue facade with white trim. Two sets of stairs lead to separate entrances, and a gravel pathway is visible in front. Surrounding fencing adds privacy to the outdoor area.
Condo in Boston
4.95 out of 5 average rating, 302 reviews

3-Bedroom Apt (7W2) 20-Minuite To Downtown Boston

Perfect for families and groups, this clean, newly renovated 3-level home has 1 King and 2 full size bedrooms and sofa sleeper in living room 2.5 bathrooms (including a half bath on the main floor), and thoughtful touches like snacks, coffee, wine, chargers, travel crib, and fast Wi-Fi. Located in an authentic Boston neighborhood ~20–30 min from downtown by car or transit. Expect lively local character, easy access to public transport, and normal city sounds.

Top guest favorite
A well-maintained front yard showcases a variety of plants and flowers, with stone steps leading to the entrance. The entryway features a welcoming door adorned with a wreath, complemented by a decorative planter filled with yellow flowers. A smooth, dark asphalt pathway is visible.
Guesthouse in Ashmont
4.9 out of 5 average rating, 145 reviews

Prime City Location: Private Suite-separate entry.

This quiet residential neighborhood has easy access to a transportation hub (subway/bus/trolley/taxi), is 7 miles from the airport and has restaurants and services nearby - many within easy walking distance. My Codman Hill neighborhood is a premium area and represents the best of suburbia in the city. The neighborhood hosts primarily single and double deck family homes. This community also has historic Victorian houses dating back to the 1700 and 1800's .

Popular amenities for Dorchester, Boston places to stay

When is the best time to visit Dorchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$20,918 GYDG$20,291 GYDG$20,918 GYDG$21,964 GYDG$23,010 GYDG$24,474 GYDG$24,056 GYDG$24,893 GYDG$24,893 GYDG$25,102 GYDG$23,010 GYDG$21,755 GYD
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Quick stats about vacation rentals in Dorchester

  • Total vacation rentals

    Explore 960 vacation rentals in Dorchester

  • Nightly prices starting at

    Dorchester vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 50,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    400 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 250 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    660 properties have a dedicated workspace

  • Wi-Fi availability

    950 of Dorchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Dorchester rentals

  • 4.7 Average rating

    Dorchester stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Dorchester's top spots, include Franklin Park Zoo, University of Massachusetts Boston, and Ashmont Station

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