Cottage holiday rentals in Dorchester, Boston

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Dorchester, Boston

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Guest favourite

Cottage in Scituate

4.96 out of 5 average rating, 45 reviews

Oceanside | Family-Friendly Oceanfront Home

This wonderful, family friendly waterfront 4 bedroom, 1.75 bath House is located on a privately owned beach in the Sand Hills Neighborhood of Scituate MA. It offers splendid, unobstructed views and direct access to the Atlantic Ocean and Minot Lighthouse. Enjoy the enclosed outdoor shower to rinse off after a day on the beach. The open living area has amazing views of the ocean and access to the screened in porch and wrap around deck. Inside and Outside dining space for 10 and outdoor sectional!

Guest favourite

Cottage in Essex

4.96 out of 5 average rating, 102 reviews

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Top Guest favourite

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 45 reviews

Marblehead, Cottage on Whittier, new construction

Minimum age requirement is 23 to book. Property is a new bungalow style, 760 s.f. unique home that is exceedingly comfortable. Sunny and spacious front room has a cathedral ceiling a natural light on three sides from ten large windows. Central heating and cooling. A wood burning Jotul stove adds ambience and warmth on cool evenings. A spiral staircase leads to a loft with a skylight and futon. This lends itself well to stargazing, yoga, or a work loft. Exterior electric outlet for EV charging.

Top Guest favourite

Cottage in Arlington

5 out of 5 average rating, 42 reviews

Charming Waterfront Cottage Near Cambridge/Boston

Delightful 1-bedroom guest cottage in Arlington with picturesque waterfront views and cozy interiors. Tucked away on Spy Pond, the cottage offers a peaceful retreat and a short drive to Cambridge (10 min to Harvard Square), Boston (20-25 minutes to Logan Airport), and Harvard, MIT, Tufts, BU. Comfortable furnishings and an abundance of windows overlooking the water create a bright and calming backdrop for your stay. Enjoy getting away from it all, while being close to everything you might need!

Top Guest favourite

Cottage in Hull

4.97 out of 5 average rating, 110 reviews

Retro New England Cottage - walk to the beach!

This is a private and peaceful beach retreat close to all the action. The one-bedroom cottage is the oldest in the neighborhood and full of retro charm. The house is within walking distance of Nantasket Beach and is set back from the road in a large, quiet yard. Don't worry about beach parking—the driveway is big enough to park two cars. Hull has plenty of restaurants and activities. Grab a post-swim ice cream in the summer, or drive to the beach and watch the waves roll in during the winter.

Top Guest favourite

Cottage in Winchester

4.96 out of 5 average rating, 70 reviews

The Little House - a historic New England cottage.

This old fashioned New England cottage in a pocket of wooded suburbs just 9 miles from Logan Airport. 4 miles from Lexington Green where the revolutionary war began. Inside the 128 beltway, its an oasis of calm in the heart of Metro Boston. Keyless entry for easy check in. A highly sought location for ice skating in winter. In summer, enjoy a chorus of frogs every night & ample wildlife sightings. Your hosts live next door, in a quiet, family neighborhood. Kids are welcome, parties are not.

Top Guest favourite

Cottage in Winthrop

4.98 out of 5 average rating, 464 reviews

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

Top Guest favourite

Cottage in Scituate

5 out of 5 average rating, 31 reviews

Expansive coastal views, 3/2 newly renovated

Stella Serena has undergone extensive renovations. It is a completely renovated, charming, 3/2 home with most importantly, views of the marsh and waterways of Scituate from every window. Whether you are coming to unwind, kayak, go to the beach, or all of it, Stella Serena will give you the rare place to recharge & have fun. We provide bikes, kayaks, paddleboard, cornhole for fun. A firepit & gas fireplace for relaxation. Breathtaking, everchanging views daily and incredible sunsets.

Top Guest favourite

Cottage in Lakeside Marblehead

5 out of 5 average rating, 64 reviews

In Old Town, Near Shops, Restaurants, Crocker Park

Quaint "Cottage" in historic Old Town, close to Marblehead Harbor, Crocker Park, shops, and dining, and a short distance from Fort Sewall. Historic, classic architectural detail blends seamlessly with contemporary touches. Hardwood floors, stone fireplace (decorative only), shiplap walls, and living room with breakfast bar. Modern kitchen boasts brass hardware and island. Upstairs holds 2 bedrooms, 1 bathroom. Front and back decks, outdoor dining area. 2-car off-street parking included!

Guest favourite

Cottage in Beachmont

4.89 out of 5 average rating, 18 reviews

Ocean Front cottage flat 30 day minimum

The beach starts 12 ft from the back deck, private flat on 2nd floor of cottage with a one of a kind breath taking 180 degree view of the Atlantic Ocean. Inside contains 4 season room/dining area leading into bedroom/kitchenette including full bath, and king bed. 10 minute drive to Logan Airport. Blue line T station 10 minute walk direct line to Boston. Nearby hiking trails and Revere Beach America’s first public beach. This one is a gem, come enjoy your time ocean side living.

Top Guest favourite

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 117 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Guest favourite

Cottage in Essex

4.95 out of 5 average rating, 254 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.