Family-friendly vacation rentals in Dorchester, Boston

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Top-rated family-friendly rentals in Dorchester, Boston

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Guest favorite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Jan 11 – 18

R2,342 ZAR per night

Guest favorite

Condo in Boston

4.95 out of 5 average rating, 233 reviews

Beautiful, spacious South Boston Condo, Near T

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

Oct 22 – 29

R8,059 ZAR per night

Guest favorite

Home in Framingham

4.96 out of 5 average rating, 130 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

Welcome to our Charming 1900s House! 1st Floor 1200sqft Private Rental @ our 3 Rental Property Sleeps 4 Adults/2 Children Features: Kitchen w/ Dishwasher + Essentials & Cookware Bathroom w/ Tub & Shower 2 Queen Bedrooms w/ Memory Foam Mattresses 1 Queen Memory Foam Sofa-Bed 3 Desks & Chairs Private Entrance Driveway Parking Laundry Room in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Playground/Park/Tennis Cleaned & Sanitized / COVID Conscious

May 6 – 13

R2,708 ZAR per night

Guest favorite

Apartment in Dorchester

4.88 out of 5 average rating, 628 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.

Jul 6 – 13

R2,769 ZAR per night

Guest favorite

Condo in Jamaica Plain

4.91 out of 5 average rating, 216 reviews

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.

Nov 24 – Dec 1

R3,323 ZAR per night

Guest favorite

Apartment in Boston

4.98 out of 5 average rating, 252 reviews

Private & serene getaway in beautiful JP

Quiet, private & serene walk-up 3rd floor apt. Separate entrance, full bath & kitchenette. Bright and spacious. 3 blocks from the center of JP with great restaurants and shopping. 5 min. walk to the 39 bus to Longwood Area and Back Bay. 15 min. walk to the Orange Line T (subway); ten minutes to Back Bay Station on the T. 1/2 block from Jamaica Pond. 5 min. walk to the Arboretum. Our space is NOT good for people with huge luggage! Tons (truly) of street parking, no permit or restrictions.

Feb 24 – Mar 3

R3,996 ZAR per night

Guest favorite

Guest suite in Boston

4.89 out of 5 average rating, 331 reviews

Light and airy separate apt in funky Jamaica Plain

The apt. has 4 twin beds in our quirky 1880 Victorian farmhouse in central Jamaica Plain. Fast transportation to downtown Boston, Cambridge, and LMA. Separate entrance, kitchen and bathroom, shared deck. PLEASE NOTE: there are STEEP STAIRS to the unit, and a NARROW SPIRAL STAIRCASE inside the unit. Ceiling in the bathroom is LOW. People with mobility issues may find these difficult. Bulky luggage may have to stay on the main floor. PLEASE read description carefully before booking.

Jul 22 – 29

R2,970 ZAR per night

Guest favorite

Home in Lynn

4.91 out of 5 average rating, 227 reviews

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

Dec 29 – Jan 5

R2,699 ZAR per night

Guest favorite

Apartment in Randolph

4.88 out of 5 average rating, 286 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

Sep 21 – 28

R2,436 ZAR per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles. EV charging available.

Oct 20 – 27

R2,356 ZAR per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

Jun 24 – Jul 1

R2,808 ZAR per night

Guest favorite

Apartment in Boston

4.88 out of 5 average rating, 493 reviews

Serene Studio in a Perfect Location

Our 500 sf 2 room apartment is quiet, private & ideally situated in the heart of Jamaica Plain-just a 4 min. walk to the Orange Line subway and buses. It offers a super comfortable bed, and all the necessities-wifi, 4K smart TV, large eat-in kitchen, Nespresso coffee, and free on-street parking.

Oct 2 – 9

R2,845 ZAR per night