Vacation rentals in Dorchester

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Top-rated vacation rentals in Dorchester

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

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Top guest favorite
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, 211 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

Top guest favorite
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, 268 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 favorite
A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.
Guest suite in Jamaica Plain
4.92 out of 5 average rating, 244 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

Top guest favorite
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, 150 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 favorite
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 562 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Top guest favorite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 999 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Guest favorite
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.

Guest favorite
A spacious dining room is illuminated by a stylish chandelier. A large rectangular table is surrounded by six upholstered chairs. Decorative art pieces adorn the walls, and a tall plant adds a touch of greenery to the corner of the room.
Condo in Dorchester
4.83 out of 5 average rating, 109 reviews

Beautiful condo with city benefits

Nicely decorated two bedroom, one bath, spacious kitchen, dinning room, living room, back yard and deck, steps from JFK T-Stop, and short 10 minute commute to all that downtown Boston has to offer. Located blocks away from I-93 for easy access. Dorchester Brewing Company, 224, Dbar, Sugar Bowl, and Savin Bar and Kitchen are all within walking distance. My condo is located within a 5 minute walk to Carson Beach.

Guest favorite
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.

Top guest favorite
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 favorite
A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.
Condo in Jamaica Plain
4.89 out of 5 average rating, 578 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Top guest favorite
A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.
Apartment in Fort Hill
4.97 out of 5 average rating, 390 reviews

Light-Filled Luxury Apartment with View

Beautiful top floor luxury apartment in stately Victorian home. Extraordinary views of historic park as your front yard! Your own entrance through a private garden. Apartment is a studio-style open living space with full kitchen, living area, and bedroom bay with queen bed. Also includes loft bedroom with 2 twin beds.

Popular amenities for Dorchester, Boston places to stay

When is the best time to visit Dorchester?

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Quick stats about vacation rentals in Dorchester

  • Total vacation rentals

    Explore 1,060 vacation rentals in Dorchester

  • Nightly prices starting at

    Dorchester vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 50,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    410 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 260 rentals that welcome pets

  • Vacation 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 vacation 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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