
Condo holiday rentals in Dorchester
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Top-rated condo rentals in Dorchester
Guests agree: These condos are highly rated for location, cleanliness and more.

The Day-Burrill-Wadsworth-La Voix House
The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

Beautiful, spacious South Boston Condo, Near T
This beautiful townhouse is a 3 min walk to the Andrew Square (subway) station that can take you to anywhere you want in Boston or the surrounding area. Museums, colleges, Fenway Park, TD Garden, the Common, Harvard Square, Faneuil Hall, Cape Cod, Salem, the Convention Center, Boston Harbor and cruise ship terminals are many of the places you can visit. We are also a 15 min walk to the local beaches. Although the place can sleep 6, we only allow 4 guests unless arrangements are made with host.

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

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt
Discover serenity in this fully-stocked, 2nd floor unit within a Victorian home in JP. Located on a quiet street near transportation and dining options, it offers access to key destinations like Longwood Medical Area and Downtown Boston. Featuring one bedroom, a cozy living room w/ TV, fully-equipped kitchen, and bathroom, plus a spacious private deck. Rest easy on a plush king-size Tempurpedic bed & a full-sized pullout couch fitting 1 adult or 2 children. Central air for increased comfort.

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!

Spacious 5BR Condo w/parking near METRO
Beautiful two floor 5 bedroom condo in a quiet, residential neighborhood of Boston. Two blocks from the trains (T & Amtrak), easy access to Boston's many colleges and universities. Walking distance to cafes and parks. The home is located in the Forest Hills neighborhood of Jamaica Plain (Boston). 15-minutes to Backbay and 20-minutes away from Downtown via the T (trains). Parking available for two mid-sized cars (Driveway parking in tandem). No bigger than a Toyota RAV4, for reference.

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.

Luxury apt w/ sauna & deck | by airport, downtown
Welcome to your private oasis just minutes away from Logan Airport AND Boston's bustling streets. Start your day with a walk along the water, then enjoy all that Boston has to offer right nearby. 1 min. walk to the waterfront 5 min. walk to Logan Airport 10 min. Uber (or 1 MBTA stop) to Downtown Boston PARKING IS DIFFICULT: - If you’re coming during the week, parking can be hard to navigate - If you MUST bring a car, do not arrive in the evening or you may not find a spot

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

Boston Rooftop Retreat
A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

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.

Large 1+bed in historic Charlestown, Boston!
Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.
Popular amenities for Dorchester condo rentals
Weekly condo rentals

Fort Hill Inn 1 Bedroom Duplex, *Sunny Condo*

My Sweet Apartment

Modern Boston Condo, near T

Cozy High-ceiling Apartment

Luxe Boston Condo, Near T

Modern Farmhouse Condo Near Downtown Salem
Victorian Charm, Modern Style w/Private Entrance

Lovely Condo-close to Downtown Salem 1bed/1ba
Pet-friendly condo rentals

Condo in downtown Boston

Family Home + Near Downtown + Cool Backyard!

Harbor View Suite

Historic JP Brownstone with Parking. Pets Welcome!

Spacious, cozy home near Boston!

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

#2A Harvard MIT Academic Semester!

New Super Modern 2 bed in Waltham
Private condo rentals

4BR/4BA | Parking + Chef’s Kitchen | Near BU/BC

Eastie near the airport Great location

Cozy South End Corner

New 2BR/2BA LUXE Harvard & MIT w/Parking Red Line

Huge 1BR City Loft w/Skylights

"La Gemma" - a gem in the North End

Sunny Southie Modern 2 Bedroom with Deck

*NEW* 3 BR South End Duplex with A/C in the city!
Quick stats about condo rentals in Dorchester

Total holiday rentals
Explore 90 holiday rentals in Dorchester

Nightly prices starting at
Dorchester holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 5,700 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
90 of Dorchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Dorchester rentals

4.8 Average rating
Dorchester stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Dorchester's top spots, include Franklin Park Zoo, University of Massachusetts Boston, and Ashmont Station
Destinations to explore
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Gillette Stadium
- Northeastern University
- Boston Convention and Exhibition Center
- Freedom Trail
- MIT Museum
- East Sandwich Beach
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Onset Beach
- Roxbury Crossing Station
- Quincy Market
- North Hampton Beach
- Museum of Fine Arts




