Cottage holiday rentals in Boston

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.

Cozy cottage, downtown Marblehead

Step back in time when you stay at this unique and historic place in the heart of Old Town Marblehead. 2 car parking, fireplaces and a private patio. Period details throughout including exposed brick and wide pine floors. This is the perfect home for a cozy, fun getaway and ideally located to take advantage of all Marblehead has to offer. Steps to the harbor, restaurants and shopping. The property is a stand-alone single home next to The Landing, Maddies, Barnacle, Driftwood & 15 mins to Salem

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.

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.

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!

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.

Retro summer cottage - walk to the beach!

A peaceful beach retreat that's close to all the action. This one-bedroom cottage is the oldest in the neighborhood and is 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 and watch the sunset on the secluded patio.

Tranquil Waterfront Retreat

Take it easy at this unique and tranquil rustic getaway. Enjoy White Pond boating, paddle boarding and kayaking. Relax and bathe in the afternoon sun on the upper or lower outdoor deck by the water. Sit on the indoor deck desk, and write a letter, or just enjoy the view. Wake up to breathtaking, panoramic waterfront views. The perfect relaxing get away.

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.