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
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.
Apartment in Dorchester
4.91 out of 5 average rating, 311 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.
Apartment in Ashmont
4.96 out of 5 average rating, 152 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.
Apartment 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
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, 78 reviews

JP Studio - Featured on Home&Texture

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!

Guest favourite
Apartment in Neponset
5 out of 5 average rating, 19 reviews

Welcome to Your Luxurious Urban Haven!

Modern 2BR/2BA home for families, groups, or business travelers: • 2 bedrooms with queen beds • King leather sofa bed in living room serves as master sleeping area • 2 bathrooms with rainfall showers • Full kitchen, open living/dining, smart TVs, fast Wi-Fi • In-unit washer/dryer, central A/C & heat • Private and on-street parking • Quiet neighborhood near shops, parks, transit & Boston attractions. NO PARTIES AND NO UNREGISTERED GUESTS ARE ALLOWED

Guest favourite
A spacious living area features a light gray sectional sofa adorned with orange accent pillows. A round coffee table sits at the center, positioned on a soft area rug. Wall art in neutral tones is displayed above the sofa, complementing the open layout toward the kitchen.
Apartment in Roxbury
4.95 out of 5 average rating, 227 reviews

Modern/Luxury | Steps from Zoo & Golf Course

No unregistered guests on property at any time. ANY ATTEMPT OF A PARTY/GATHERING OF ANY KIND (birthday/house/event) will result in an immediate on site termination of stay with NO REFUND. Newly renovated luxury 4 bdrm/2 bath apartment on the 3rd floor in Boston. Amenities: - Fully equipped kitchen (Complimentary Coffee, Snacks, and Water) - Hi-Speed Wifi - 75" 4k TV w/ Disney+/Netflix/Hulu included w/ stay. - Access to fully equipped private gym

Top Guest favourite
A cozy outdoor patio area is framed by a wooden fence and surrounded by greenery. Vibrant yellow chairs and a matching table are positioned on brick pavers, inviting relaxation. The natural setting includes stones and plants, creating a tranquil garden space.
Guest suite in Jamaica Plain
4.89 out of 5 average rating, 142 reviews

Urban Guest Suite

Come stay at the guest suite in our quirky, historic home in Jamaica Plain, one of Boston's most diverse and exciting areas. The suite is on the ground floor with a private patio and private entrance. Guests enjoy their own private space with a bathroom, queen size bed, and work area. Located 2 blocks away from the Stony Brook Orange line “T” and a 10 minute walk to local restaurants and super markets.

Guest favourite
A spacious bedroom features a large bed with a white comforter. Natural light is provided by two windows, and a small desk with a chair sits in one corner. A green plant adds a touch of nature, while light wood flooring completes the inviting look.
Private room in Roxbury
4.79 out of 5 average rating, 233 reviews

King Bed | 3rd Floor | Sunny

Located on the third floor of my townhouse. You will take two flights of stairs to the top and enjoy this oversized King bedroom in the geographical middle of the city. 15 min walk to the subway and 5 min walk to the bus station. Your room is equipped with a personal fridge and microwave. This home has classic charm with contemporary touches. You will share a bathroom with two other guests.

A modern living room features a comfortable sectional sofa with a light gray fabric, complemented by a glass coffee table. Colorful rugs add a vibrant touch, while large windows allow for natural light. Wall art and decorative elements enhance the inviting atmosphere.
Home in Roxbury
4.88 out of 5 average rating, 24 reviews

Cute, quiet 2br house near South End

Private, peaceful, newly renovated house. The bedrooms are on the second floor. One has a queen bed, dresser and closet. The second bedroom has a single bed. The house is surrounded by trees and the guest rooms are in the ideal spot, with sun in the afternoon and minimal external light after dark.

Top Guest favourite
A modern living area features a grey couch adorned with orange and blue pillows. A large flat-screen television is mounted on the wall above a sleek dining area with four high-backed chairs. Contemporary artwork adds a vibrant touch to the space, complemented by warm wooden floors.
Apartment in Boston
4.98 out of 5 average rating, 53 reviews

Brand New 2BR Apt 20Min Downtown Boston

Welcome to my Brand-New, 2-Bedroom with 3 beds, home nestled in a prime location near Franklin Park and just 5 miles away from Downtown Boston. Whether you’re visiting for business or pleasure, this stylish and comfortable space offers the perfect blend of convenience & tranquility.

Popular amenities for Dorchester holiday rentals

When is the best time to visit Dorchester?

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Avg. price$144 NZD$151 NZD$159 NZD$176 NZD$184 NZD$196 NZD$192 NZD$199 NZD$199 NZD$201 NZD$184 NZD$174 NZD
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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 $33 NZD 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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