Holiday rentals in Dorchester

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Top-rated holiday rentals in Dorchester

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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
Guest suite in Jamaica Plain
4.92 out of 5 average rating, 247 reviews

Ann and Esther's Cozy Studio near the Heart of JP

This airy and light private studio is set in a beautiful, secluded backyard/garden. Close 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 microwave, fridge, counter w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

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 outdoor living area is showcased, featuring comfortable seating and a central table. Warm string lights illuminate the space, while an umbrella provides shade over part of the seating. A patterned rug anchors the furniture arrangement against a backdrop of greenery.
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.

The bright bedroom features two spacious beds dressed in red and navy bedding. An accent wall of exposed brick provides texture, while large windows allow natural light to fill the room. A TV is positioned on a stand against the wall.
Flat in Meeting House Hill
4.67 out of 5 average rating, 49 reviews

I New apartment Luxury in Boston

Renovated Boston apartment with modern amenities, a full bath, new heating/cooling, WiFi, TV, and washer/dryer. Convenient public transport on a bus line connecting to trains for quick access to downtown Boston, Quincy Market, Fenway Park, Franklin Park Zoo, South Bay Shopping, Boston University, Boston Hospital, Mass General, MIT, Harvard, Boston Convention and Exhibition, Hynes Convention , AMC Theater. Attractions Museum of Fine Arts, JFK Presidential Library, and the Neponset River trail.

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
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.

Flat in Neponset
4.72 out of 5 average rating, 96 reviews

Charming vintage apartment!

20 minutes to downtown! Quiet and Private apartment! Our adorable vintage themed apartment is located in a neighborhood south of Boston in Dorchester, within walking distance to great bars and restaurants. Free parking and lots of amenities. Lots of space to stretch out and relax. We are also an easy drive to Cape Cod , Salem Mass and other quaint New England towns. We can suggest easy day trips to New Hampshire, Maine, Western Mass and Connecticut destinations as well.

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!

A vibrant view of a neighborhood is framed by lush green tree branches. Rooftops of various buildings, including some with red accents, are visible below, with the distant horizon suggesting a body of water beyond.
Guest suite in Dorchester
4.87 out of 5 average rating, 145 reviews

Treetop+Balcony Suite, ocean view, safe, nr metro

Ocean views, harbor islands in the distance, huge trees with cardinals and blue-jays, large private balcony, private bath and kitchenette/dining room. Safe neighborhood walking distance from reliable red-line subway station, 15 minutes ride to historic center! Queen-size bed in private room, fold-down full-size bed in living room; charming Victorian house has high ceilings, wood floors. Walk to local beaches and restaurants, bike paths, JFK museum. STR 443035

Top guest favourite
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
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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