Vacation rentals in Dorchester

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Top-rated vacation rentals in Dorchester

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Top guest favorite
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, 178 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!

Superhost
An inviting entryway is adorned with a decorative mirror and a houseplant next to a console table. The living area is visible in the background, featuring a comfortable black sofa, a patterned area rug, and a mounted television on the wall.
Home in Dorchester
4.91 out of 5 average rating, 150 reviews

New Spacious Home in Boston

Welcome to our spacious urban retreat in the heart of Boston. This well maintained 4 bedroom unit is conveniently located near many city attractions. Enjoy quiet patio, backyard and free coffee bar. Great for a quick getaway or special gathering. 5 min walk to access bus and train 10 min drive to UMass Boston and JFK Library 20 min drive to Fenway Park and TD garden sports 10 min drive to the famous Franklin Park Zoo/Golf Course 20 min drive to Historical Downtown Boston and Prudential Shopping

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, 163 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
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Apartment in Nahant
4.94 out of 5 average rating, 160 reviews

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

Guest favorite
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, 158 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 favorite
A bright living space features large windows allowing natural light to fill the room. Two distinct seating areas are present: a cozy armchair with a patterned throw, and a sofa with decorative pillows. A wooden coffee table sits centrally, complemented by a small dining area in the background.
Apartment in Cambridge
4.99 out of 5 average rating, 160 reviews

Cambridge Retreat - Sunny 2BR - Close to Harvard

Beautiful two bedroom apartment on the first floor of a classic two-family home in West Cambridge. A corner lot in a quiet neighborhood, with a grassy yard on three sides and small city garden across the street. A block from Danehy Park, a five minute walk to Huron Village and Fresh Pond Reservation, a twenty minute walk to Porter Square, and a quick bus ride to Harvard Square. A perfect home base for college tours and working vacations. The owners, long time Airbnb travelers, live upstairs.

Top guest favorite
A charming yellow Victorian house is framed by lush greenery and tall trees. The front porch features white railings and steps leading to the entrance, with plants adding a welcoming touch. Sunlight softly illuminates the exterior, highlighting the classic architectural details.
Apartment in Dorchester
4.89 out of 5 average rating, 683 reviews

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

Top guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 217 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Top guest favorite
A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.
Condo in Salem
4.95 out of 5 average rating, 105 reviews

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Top guest favorite
A bright and airy living area features large windows with natural light streaming in. A white sectional sofa with a yellow decorative pillow faces a modern entertainment unit. The exposed brick wall adds character to the space, which is complemented by warm bamboo flooring.
Condo in South End
4.94 out of 5 average rating, 247 reviews

SouthEnd Penthouse

Centrally located penthouse unit in the heart of Boston SouthEnd. Abundance of sunlight, spacious living area, and open kitchen will make your stay a unique and charming experience in a historically preserved area. Ideal to explore the local neighborhood restaurants or walk to Boston commons, the ballpark, downtown or Newbury Street. The neighborhood is historic to Boston with classical brick stone look and the place itself is quite a gem, very quiet and open dining+living room style.

Top 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
4.98 out of 5 average rating, 82 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 favorite
An open kitchen is paired with a comfortable living area, featuring light hardwood floors. The kitchen includes modern appliances and a spacious island with seating. A neutral-colored sofa and coffee table create a relaxed ambiance, with plants adding a touch of greenery in the background.
Condo in Boston
4.95 out of 5 average rating, 301 reviews

3-Bedroom Apt (7W2) 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.

Popular amenities for Dorchester, Boston places to stay

When is the best time to visit Dorchester?

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Avg. priceG$20,922 GYDG$20,294 GYDG$20,922 GYDG$21,968 GYDG$23,014 GYDG$24,479 GYDG$24,060 GYDG$24,897 GYDG$24,897 GYDG$25,106 GYDG$23,014 GYDG$21,759 GYD
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Quick stats about vacation rentals in Dorchester

  • Total vacation rentals

    Explore 960 vacation rentals in Dorchester

  • Nightly prices starting at

    Dorchester vacation rentals start at G$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 50,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    400 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 250 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    660 properties have a dedicated workspace

  • Wi-Fi availability

    950 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 Ashmont Station

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