Holiday rentals 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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Guest favourite
Flat in Medford
5 out of 5 average rating, 7 reviews

ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk

Located minutes from Tufts/Somerville, Cambridge, and Boston. This recently renovated flat offers a spacious, chic, open concept design with hardwood floors, lots of natural light, blackout shades, and glass markerboards. Modern kitchen equipped with stainless steel appliances and coffee machine. Stylish living room features a 65" flat screen smart TV, floating shelves, and adorable couch. Comfy bedroom offers a memory foam mattress, powered stand-up/sit-down Uplift Desk, and foldable treadmill.

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, 267 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.
Flat in Dorchester
4.91 out of 5 average rating, 310 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

Guest favourite
A cozy lofted bedroom features a spacious bed with white bedding and a low ceiling with angled walls. Natural light enters through a nearby window. A small nightstand stands beside the bed, while a minimalist shelf holds personal items along the wall.
Private room in Fort Hill
4.92 out of 5 average rating, 607 reviews

AKBrownstone: Loft rooftop views by T

🏠 Live like a local: cozy, lofted bedroom, in a classic Boston Brownstone 🚾 Frequently professionally maintained home, clean shared bathroom 🚇 5 mins walk to the T (Orange Line Subway), 3 stops to Back Bay city center, or go on bike & walking path 👣 Walk to Longwood Medical Area, Museum of Fine Arts, Northeastern, & Fenway Park 🌳 Sunny south/west windows overlooking a park & community garden 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Superhost
A full kitchen is featured, showcasing a large granite counter with seating and a blend of modern appliances, including a gas stove and refrigerator. Exposed brick walls add texture, while natural light enters through windows, creating a bright and functional space.
Flat in Roxbury
4.79 out of 5 average rating, 182 reviews

A King Bed | Apartment | Middle of Boston

Located in the geographical middle of Boston you can get to anywhere in the city within 20 minutes including Harvard/MIT, Downtown, Fenway, Hynes Convention Center, Seaport and more. This pseudo apartment on the first floor is separate from the rest of the house and has its own private entrance, a private bathroom and a dedicated off street parking spot. The full kitchen with oversized counter is great for eating; comfy living room for relaxing and an office nook for working.

Guest favourite
The spacious bedroom features a king-sized bed with a dark quilt and layered patterned bedding. Soft lamps provide ambient lighting on either side of the bed, which is set against a wall adorned with dark curtains. A flat-screen TV is positioned across from the bed, with an air conditioning unit nearby.
Guest suite in Melrose
4.92 out of 5 average rating, 567 reviews

Private Suite-Free Parking,near Boston Airp-Train

--> 7 miles N of Boston & a near subway, beaches, & airport (93, 95 & Rte 1), you’ll find the quaint city of Melrose. During 11/25 - 3/26 longer stay are possible. Please inquire. The Melrosian Suite is nestled behind other houses. Wake up to the chirping birds instead of Boston’s noise. 225 acres of ponds, trails & conservation lands are at top of street w/ distant views of Boston & the ocean. Before booking, check out info required when you book & house rules.

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, 76 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
Private room in Brighton
4.96 out of 5 average rating, 106 reviews

Large Sunny room free parking

Our address is 42 Brooksdale road Brighton MA 02135. The room is with shared one kitchen and three bathrooms. Easy access to Mass pike/128. Free parkings. From our house to Downtown Boston is about 15 minutes drive. Near Harvard university, Boston college, Fenway. Bus 64 station is 5 minutes away from our house to center square/MIT. Bus 57 is about 15 minutes walk distance to kenmore square/Coply. Bus 86 station is also 15 minutes walk distance to Harvard university.

Superhost
Private room in Dorchester
4.87 out of 5 average rating, 118 reviews

Boston Queen Room 1.1

This beautiful Boston private bedroom is outfitted with a queen sized Casper mattress, Casper pillows, hypoallergenic bedding, free wifi and digital door lock. This space also has a shared kitchen, shared living room and shared bathroom with all the amenities needed to feel at home. NO PARTIES, NO EVENTS, NO DRUGS On the morning of your arrival the full check-in instructions will be sent, including all codes to make your self check-in process seamless.

Guest favourite
Flat in Neponset
5 out of 5 average rating, 11 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.

Guest favourite
Home in Dedham
4.84 out of 5 average rating, 570 reviews

Private apartment close the city!

New couch! New towels and linens! Fresh paint! New flooring coming soon. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.

Top guest favourite
Private room in Neponset
4.9 out of 5 average rating, 203 reviews

Private room/ MUST LOVE DOGS

Large room with a king size bed in a great condo in a nice neighborhood in Boston. Close to public transport, city beaches and bike paths. Convenient access to major highways. Use of kitchen. Shared bath. Plenty of on street parking. Laundry facilities if needed.

Popular amenities for Dorchester holiday rentals

When is the best time to visit Dorchester?

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Quick stats about holiday rentals in Dorchester

  • Total holiday rentals

    Explore 1,010 holiday rentals in Dorchester

  • Nightly prices starting at

    Dorchester holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 50,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    410 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 240 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    670 properties have a dedicated workspace

  • Wifi availability

    1,000 of Dorchester holiday rentals include wifi 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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