Holiday houses 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
The kitchen features white cabinetry and stainless steel appliances, with a spacious layout for cooking. A game table is shown with a pool table in the background. A cozy living area includes a light blue accent wall and comfortable seating. The backyard displays a grassy area with a slide and a playset.
Home in South Boston
4.99 out of 5 average rating, 213 reviews

Family Friendly City Oasis! Free Parking, King Bed

Welcome to The Southie House! An epic private home for a family vacation or conference in the Heart of Boston! Close to the Red line T for access to downtown, Cambridge & local universities, and short ride to the BCEC. At the same time a short walk to the beach for relaxing. Enjoy the back yard oasis with the whole group! This home provides you with a private place to relax after a full day of exploring, ensuring you have all the comforts of home while traveling. COME SEE OUR NEW GAME-ROOM & GYM

Guest favourite
A cozy bedroom features soft pink walls and a large window dressed with light curtains. A plant enriches the space atop a wooden dresser, while framed artwork decorates the walls. A comfortable armchair and a small footstool are positioned on a vibrant area rug.
Apartment in Jamaica Plain
4.89 out of 5 average rating, 201 reviews

Artistic charm in hip J.P.

It's a quaint efficiency apartment with a private entrance, private bathroom, full kitchen, eat in area and a work space. The bedroom is roomy with a comfy bed perfect for a single traveler or a couple. The apartment is thoroughly cleaned for each guest and all bedding is washed prior to your stay. 5 minute walk to the MBTA train downtown. 10 walk to the bus to hospitals and Museum of Fine Arts. Close to Jamaica Pond and many parks, restaurants, Sam Adams Brewery, grocery shops and bike rentals.

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, 269 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
The entrance features a set of elegant stone steps leading to a covered porch. Flanking the steps are decorative stone lion statues and lush greenery, including vibrant pink rhododendron blooms adding color to the welcoming atmosphere.
Apartment in Jamaica Plain
5 out of 5 average rating, 89 reviews

Victorian Treetop Apartment - Close to Everything!

My home is perfect for Families, Business / Medical professionals, or those travelers looking for a comfortably furnished pied-a-terre for an extended family and friend visits while working remotely or discovering New England. We are close to public transportation, Whole Foods Market, local restaurants/pubs, hospitals, universities and schools. You’ll love my place because of the friendly neighborhood filled with Victorian homes, the public parks, the light open loft-like rooms, the comfy beds.

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.
Apartment in Ashmont
4.95 out of 5 average rating, 155 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.
Condo 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 modern kitchen features white cabinetry and sleek stainless-steel appliances. A large central island with seating for four is complemented by a stylish backsplash. Natural light enters through the window, highlighting the space's clean lines and functional layout.
Apartment in Wollaston
4.99 out of 5 average rating, 69 reviews

Stunning, New, 2BR Close Boston

Stunning New 2 BR, in Quincy, 7 miles to Boston, walk to train station- 5 stops to Boston South Station. ✔ Sleek new Modern custom built 2-bedroom, 2 floors ✔ Highest Speed Wi-Fi- Gigabit Plus speed ✔ Luxury living- Matouk luxury linens, towels and pillows ✔ Luxury King Sized Hybrid Mattresses ✔ Furnishings from Restoration Hardware and CB2 ✔ Private outdoor deck and patio with Pollywood Adirondack Chairs ✔ Great Location- In City of Quincy, walk to stores, restaurants, close to Boston

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.
Apartment in Dorchester
5 out of 5 average rating, 14 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.

Guest favourite
An open kitchen and living area features sleek cabinetry and high-end appliances. The space includes a comfortable couch, a coffee table, and bar stools at the kitchen island. Hardwood floors extend throughout, complemented by a modern rug and a view of laundry machines in the corner.
Apartment in Dorchester
4.93 out of 5 average rating, 250 reviews

3-Bedroom Apt (7B2) 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.

Guest favourite
A welcoming entry area features two patterned chairs surrounding a small glass table, positioned beside a staircase. A flat-screen television is mounted on the wall, and local brochures are displayed on a nearby stand, enhancing the space's convenience.
Condo in Roxbury
4.94 out of 5 average rating, 236 reviews

Modern & Cozy 3-BR Condo near Downtown

This listing was ranked best new Airbnb in MA for 2022! Book now to experience our lovely, cozy in-law suite with all the essentials you need for a comfortable stay. Conveniently a very short drive from city attractions, universities, hospitals, and the airport, you'll have easy access to everything Boston has to offer. Plus, easy access to major highways makes exploring a breeze. Don't miss out on this well-maintained and nicely furnished space.

Top Guest favourite
A cozy bedroom features a queen size bed dressed in crisp white linens, complemented by a decorative pillow. Black and white patterned curtains frame two windows, allowing natural light. A nightstand with a lamp is positioned beside the bed, enhancing the room's warmth and functionality.
Home in Boston
5 out of 5 average rating, 32 reviews

Best Place To Rest

A unique and tastefully envisioned space, this fully renovated private apartment was designed as an idyllic and cozy getaway. This fully furnished unit is ready to accommodate groups, couples, or families. Accommodations for daily, weekly, or monthly bookings are available. We are committed to creating a comfortable experience for all of our guests. We look forward to sharing our Best Place to Rest with you!

Guest favourite
A modern dining area is depicted, featuring a sleek glass table surrounded by six white chairs. Natural light filters through four large windows, highlighting the red area rug beneath. A sideboard with a mirrored surface is positioned against one wall, contributing to the contemporary design.
Apartment in Dorchester
4.86 out of 5 average rating, 85 reviews

Large apartment for up to 8 ppl/3rd floor

Amazing location: only 3 stops (Red Subway/Metro/T line) to MGH; downtown Boston; South Boston , Seaport District. variety of cafes, restaurants, bars, convenience/grocery/pharmacy stores minutes away. Close to everything Boston has to offer! Less then 10 mins drive to MGH, DFCI, downtown Boston, Cambridge, Brookline, etc and plenty of street parking spots available!

Popular amenities for Dorchester holiday rentals

When is the best time to visit Dorchester?

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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 $28 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    1,050 of Dorchester holiday 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 Roxbury Community College

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