Holiday rentals in Dorchester

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Top-rated holiday rentals in Dorchester

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

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Top guest favourite
A bright and airy room features a comfortable bed adorned with colorful bedding. Two wooden desks with chairs are positioned thoughtfully, along with various seating options. Natural light filters through a window, accentuating the room's warm wood flooring and blue walls.
Guest suite in Dorchester
4.9 out of 5 average rating, 174 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 favourite
A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.
Guest suite in Ashmont
4.96 out of 5 average rating, 270 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

Top guest favourite
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Flat in Ashmont
4.96 out of 5 average rating, 159 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, 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.

Top guest favourite
A spacious living room is showcased with large windows offering natural light. Comfortable seating includes a light green sectional sofa and a white couch. A wooden coffee table sits atop a colorful area rug. A flat-screen television is mounted on the wall, providing entertainment options.
Apartment in Dorchester
4.97 out of 5 average rating, 157 reviews

1st floor, free parking off street, 3 min to train

1BR private first floor condo that has it all. Suitable for families, vacationing, and remote work. *Please note we live on the 2nd Floor (separate entrance) - FREE PARKING off-street driveway for 1 vehicle - PUBLIC TRANSIT 2 short blocks from Red Line, downtown in 15 min - SMART HOME High Speed dedicated Wi-Fi, smart speakers and lighting - WALKERS PARADISE Walk score 91 , many bars & restaurants & conveniences - PARKS Savin Hill & Beach within 10 min walk, near Carson Beach & Harbor walk

Top guest favourite
A charming yellow Victorian house is framed by lush greenery and tall trees. The front porch features white railings and steps leading to the entrance, with plants adding a welcoming touch. Sunlight softly illuminates the exterior, highlighting the classic architectural details.
Flat in Dorchester
4.89 out of 5 average rating, 682 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.

Superhost
The exterior of a two-story single-family home is presented, featuring a light-colored siding and a pitched roof. A set of steps leads to the welcoming front entrance, framed by a well-maintained garden with blooming flowers. A black iron fence borders the property, enhancing its curb appeal.
Guest suite in Ashmont
4.82 out of 5 average rating, 207 reviews

Charming 3 bedroom suite in the heart of Boston

Located in the heart of Boston, our newly renovated, single family home is only an 8 min. walk to the Red Line train which takes you straight to the center of historic Boston. We are conveniently close to Boston attractions, but located on a quiet residential street with off-street parking and free charging for your electric vehicle. The suite has three ample-sized bedrooms, private newly-renovated bathroom, and a kitchenette. Guests have a separate front door entrance with PIN access.

Guest favourite
Home in Dorchester
4.91 out of 5 average rating, 11 reviews

3B fam/friendly Bostons best deal: 5 min from MBTA

Step into modern comfort in the heart of the city. This 3 bedroom retreat blends practicality with warm touches. Whether you’re here to explore, catch a show, or simply unwind, you’ll find everything you need. Located just steps from the city’s best cafés, gourmet markets, you’re walking distance of popular nightlife spots, and quick transit links. Perfect for solo adventurers, couples, or business travelers, this urban hideaway is your launchpad for the very best the city has to offer.

Guest favourite
A comfortable living room features a light-colored sofa adorned with yellow pillows, situated near a television on a modern stand. A round coffee table occupies the center, with a small plant adding a touch of greenery. Natural light filters through the windows, highlighting the room's inviting design.
Flat in Dorchester
5 out of 5 average rating, 15 reviews

Newly Renovated Retreat l Near T

Relax with this centrally located home offers the best of both worlds: a peaceful suburban feel and easy access to Boston's cultural diversity. You are also within a mile of Castle Island Beach and numerous restaurants. This well-maintained first-floor unit has three bedrooms, one bathroom, and a modern, cozy interior for a true "home away from home" experience. With two parking spaces and a 7-minute walk to the JFK/UMass train station, it is a convenient and comfortable place to stay.

Superhost
The living room features a dark couch adorned with light blue pillows, positioned opposite a mounted 65-inch television. Natural light filters through two windows, and a small side table is placed next to the couch, creating a functional and open space.
Flat in Boston
4.91 out of 5 average rating, 211 reviews

1-Bedroom Apt (7B1) 20-Minuite To Downtown Boston

Prime Location: Located just a 10-minute walk from buses and the commuter rail, our guests enjoy a swift 15-minute train ride to downtown Boston. With Fenway Park, TD Garden, and Boston Logan Airport within a short distance, our apartment serves as your gateway to the best of Boston. Our newly built 1-BR lower-unit apartment is perfectly near the vibrant heart of Boston. For both leisure and business travelers, offering a serene stay with easy access to Boston’s bustling city life.

Guest favourite
The living area features a modern sofa set adorned with decorative pillows. A simple coffee table sits between the seating arrangements, accented by a small plant. A piece of wall art adds color to the light gray walls, while a window allows natural light to enhance the space.
Guest suite in Ashmont
4.97 out of 5 average rating, 78 reviews

Cozy and Clean Ashmont Apartment

Kick back and relax in this peaceful sanctuary, with easy access to all of Boston. This apartment is the entire third floor of our home, and has a separate entrance for maximum privacy. Enjoy amenities like a king sized bed, air conditioning, smart TV loaded with Netflix and Hulu, a washer/dryer, and a full kitchen (including a dishwasher). The location is just a couple blocks from two red-line T (subway) stations, where you can get to downtown Boston in less than 20 minutes.

Top guest favourite
A well-lit sleeping area features a spacious bed adorned with white linens and a soft gray blanket. An artistic wall hanging adds a splash of color above the bed. Sheer curtains frame the window, enhancing the serene ambiance of the room.
Flat in Roslindale
4.97 out of 5 average rating, 31 reviews

Cozy 1BR suite in Boston's Roslindale Village

This is a 1BR suite on the 2nd floor of our newly renovated home in Boston's Roslindale, which is about 6 miles or 20 min away from downtown (please look up the neighborhood to have a clear idea where it is). Our place is close to restaurants & bars in Rozzy Village and West Roxbury. There is a connection via bus at the corner to the subway at the Forest Hills Orange Line T-stop that will get you to downtown in about 20 min, and there is commuter rail in Roslindale Village.

Guest favourite
A modern kitchen is visible, featuring stainless steel appliances, including a gas stove and a large kitchen sink. A dining table made of dark wood is surrounded by red metal chairs, providing a casual dining option. Natural light fills the space through a large window.
Flat in Wollaston
4.95 out of 5 average rating, 284 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. One bedroom unit with a pullout couch in living room.

Popular amenities for Dorchester holiday rentals

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Quick stats about holiday rentals in Dorchester

  • Total holiday rentals

    Explore 1,060 holiday rentals in Dorchester

  • Nightly prices starting at

    Dorchester holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 50,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    410 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 260 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    710 properties have a dedicated workspace

  • Wifi availability

    1,050 of Dorchester holiday rentals include wifi 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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