Holiday rentals in Dorchester

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Top-rated holiday rentals in Dorchester

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Top guest favourite
A spacious living area features a comfortable gray sofa with decorative cushions and a wooden coffee table. Natural light streams through multiple windows, highlighting gleaming hardwood floors. A dining table with white chairs is visible, alongside an air conditioning unit and a wall-mounted art piece.
Flat in North Quincy
4.98 out of 5 average rating, 105 reviews

Home Away from Home | Next to Boston & Beach, EV+

Enjoy a comfortable stay in this beautiful, newly renovated 2 bedroom apartment less than a 10 min walk to the beach and convenient access to Boston by car (15-25min) or public transportation (30-45min). It's a spacious 1200 sqft, was just fully remodeled, retains plenty of character and boasts loads of windows and light. Recharge from your trip in style with a fully equipped kitchen, two comfortable king beds, 55" smart TV, new sofas, work & dining area, sun porch, AC and free street parking.

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 Boston
4.9 out of 5 average rating, 172 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, 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

A modern living area showcases an open layout with a comfortable seating arrangement. Natural light fills the space through large windows. A dining table is set nearby, complemented by stainless steel appliances in the kitchen. Decorative elements enhance the overall design.
Flat in Dorchester
4.91 out of 5 average rating, 313 reviews

Swanky unit Convenient to Downtown nr Restaurants

My Swanky pad is a modern renovated garden level unit with a great open layout. Is very clean, comfortable, has private entrance, high ceilings, large windows which project great natural light into the space. Consist of: -- Kitchen w. Dining Space (work space) --Stainless steel appliances, full stove, refrigerator & over the range microwave --Keurig Coffee ( Complimentary coffee ), Electric hot water kettle --Large closets --55" Smart Tv in living room --High Speed WIFI --Full Bath with Tub

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
4.95 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.

Guest favourite
A micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.
Flat in Fort Hill
4.9 out of 5 average rating, 938 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Guest favourite
Home in Meeting House Hill
4.86 out of 5 average rating, 7 reviews

Just Book It: best deal in Boston 3Br

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
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 cozy sleeping area showcases a spacious bed with soft white linens. Two round pendant lights are suspended on either side, illuminating abstract artwork above the headboard. Textured wall decor adds warmth, creating an inviting atmosphere.
Guest suite in Jamaica Plain
4.99 out of 5 average rating, 79 reviews

JP Studio - As Seen on Apartment Therapy

We’re thrilled to share our newly finished garden-level studio! Thoughtfully designed for comfort, it includes a queen-sized bed, cozy living area, kitchen, and private bathroom. Just a 5-minute walk to the Stony Brook train stop, it offers easy access to Boston. Nearby, explore attractions like the Zoo, Arnold Arboretum, and Jamaica Pond. The neighborhood features excellent dining, breweries, and cafes. Let us know if you’d like recommendations—we’d love to share!

Top guest favourite
The open kitchen and dining area feature a round dining table surrounded by four chairs. Natural light fills the space through large windows, illuminating the glossy stained hardwood floors. A decorative plant adds a touch of greenery, enhancing the overall inviting ambiance.
Flat in Wollaston
4.96 out of 5 average rating, 211 reviews

Short Train 2 Boston, Luxury prvt unit w parking

Enjoy a comfortable stay in this private entrance, beautiful, newly renovated 1 bedroom apartment only a short 4 minute walk to Wollaston train station- 5 stops to downtown Boston. Convenient access to Boston by car (15-20min) as well. Full gut-renovation, open floor kitchen/dining room. Gorgeous bathroom. New HVAC system. W&D in unit. Off street parking spot right next to separate, private entrance. Great neighborhood, beautiful park across the street.

Guest favourite
A cozy bedroom is presented with a full bed dressed in vibrant patterned bedding. A mirror is mounted on the wall, reflecting natural light that brightens the space. The flooring features a large area rug, adding warmth to the room's ambiance.
Flat in Meeting House Hill
4.81 out of 5 average rating, 222 reviews

Victorian 3rd Floor Unit

We are a 15-minute drive to Downtown Boston, Logan Airport, major Universities, historical sites like Castle Island, the beach, museums, State Parks, and major shopping malls. It is easily accessible by trains or buses (5-minute walk to the T and a 15-minute train ride to Downtown Boston). Steps away from local restaurants, cafes, bakeries, and markets on the main street. Free on-street parking.

Guest favourite
Home in Meeting House Hill
4.95 out of 5 average rating, 19 reviews

Central, Stylish Home in Quiet Boston Neighborhood

Welcome to Hilltop Haven, a stylish and spacious 4-bedroom, 2-bathroom single-family home tucked into a peaceful corner of Boston. With room for up to 8 guests, this modern retreat offers all the essentials for a relaxing city stay—whether you’re in town for business, family time, or a quick escape.

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 £15 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 Roxbury Community College

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