Cottage vacation rentals in Boston

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Top-rated cottage rentals in Boston

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Guest favorite

A sunset over the lake creates a vibrant display of pinks and purples reflected in the calm waters. The surrounding trees frame the scene, enhancing the tranquility of the natural landscape.

Cottage in Essex

4.96 out of 5 average rating, 101 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.

Guest favorite

A comfortable living area features a blue sofa and a cozy armchair with an accent pillow. A small wooden coffee table rests on a patterned rug, while sunlight streams through sheer curtains. A wall-mounted TV and open door provide a welcoming touch.

Cottage in Rockport

5 out of 5 average rating, 7 reviews

Charming Rockport Cottage ~Walk to Ocean~Parking

Step into this charming 1BR / 1 Bath cottage in a tranquil area just a few steps away from Shalin Liu Performance Center, artsy Bearskin Neck, beautiful waterfront, and many exciting attractions. Explore the picturesque town before returning to the lovely oasis, whose gorgeous design, colorful garden, and rich amenity list will mesmerize you. ✔ Comfortable Bedroom ✔ Lovely Living Room ✔ Fully Equipped Kitchen ✔ Flower Garden ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Onsite Parking Learn more below!

Top guest favorite

A rustic exterior of a cottage is shown, with wooden siding and large windows framed by flower boxes. A seating area with blue chairs surrounds a stone fire pit, while string lights are hung overhead, creating a cozy outdoor ambiance among the trees.

Cottage in Hull

4.97 out of 5 average rating, 108 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.

Superhost

The exterior of the cottage is depicted, featuring a two-story structure with gray shingles and a blue accent trim. A porch with white chairs overlooks a rocky shoreline and the Atlantic Ocean, while the landscape is dotted with lush greenery in the distance.

Cottage in Rockport

4.82 out of 5 average rating, 45 reviews

Rustic, Charming Cottage on Atlantic Ocean

Charming and unique summer cottage overlooking Sandy Bay on historic Bearskin Neck in Rockport, MA. Wake up to gorgeous sunrises and the sound of surf. Located in the heart of the town's historic district, the cottage is steps away from shops, art galleries, restaurants and Motif #1. Features three bedrooms with a total of 6 beds, two bathrooms and a shower, a well-equipped kitchen, secure WIFI, a Roku Smart TV, a parking space for a sedan or compact SUV, and the beauty of the Atlantic Ocean.

Guest favorite

Cottage in Westford

4.92 out of 5 average rating, 38 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Top guest favorite

A spacious wooden deck is surrounded by blooming flowers and greenery. A swing with a blue cushion is positioned for relaxation, adjacent to a cozy corner in a well-maintained yard. The background features a charming gray house with multiple windows.

Cottage in Winthrop

4.98 out of 5 average rating, 460 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 favorite

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 115 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 favorite

A wooden deck overlooks marsh views, featuring tall bar stools and small tables arranged neatly. Guests can be seen enjoying their time at the water's edge as the sun sets, casting a warm glow across the scene.

Cottage in Essex

4.95 out of 5 average rating, 253 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.

Top guest favorite

A roof deck offers expansive ocean views, extending to the horizon. Grey lounge chairs are positioned on a light-colored deck, allowing for comfortable relaxation. The calm sea reflects the sky, while the rugged coastline is visible in the background.

Cottage in Rockport

4.97 out of 5 average rating, 63 reviews

Bearskin Neck oceanfront w/ 2 parking spots!

Come share our vacation cottage! Bearskin Neck, at the tip of Rockport, is a perfect location combining the convenience of being nestled in the center of town, with the sounds and views of being next to the ocean. Originally built as a fishing cottage, the structure and beams have been preserved, but updated with the conveniences and comforts of a modern home. Walk to beaches, shops, restaurants and coffee shops. Property is managed and cleaned by owners.

Guest favorite

A lighthouse is visible standing on a rocky shoreline, surrounded by calm waters. The structure features a white tower topped with a green lantern. In the background, a house is nestled among trees with a clear view of the lighthouse.

Cottage in Gloucester

4.97 out of 5 average rating, 126 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Guest favorite

The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.

Cottage in Stow

4.95 out of 5 average rating, 174 reviews

White Pine Cottage

Cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are visiting the area. Located in quiet neighborhood with very little traffic. Convenient to local farms, orchards, golfing, parks and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 168 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

Quiet 3BR + den, 2BA cottage sits on a creek with a lovely deck overlooking the tidal marsh which opens up to Essex Bay. Comfy beds, light and airy space. Quiet neighborhood surrounded by nature. Train to Boston is 2 miles from the house, local hikes, bike rides and beaches all a short walk, drive or bike ride away.