Cottage vacation rentals in Middlesex County

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Top-rated cottage rentals in Middlesex County

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite

The cottage is framed by vibrant flower beds featuring a variety of colorful blooms. Tall trees provide shade, complementing the lush greenery of the surrounding yard. The structure includes large windows, showcasing a welcoming façade with a gently sloped roof and a detached garage.

Cottage in Worcester

Unique and Private Cottage in Worcester

Unique and private - your own cottage in the desirable West Side of Worcester. The carriage house of a larger property, the cottage is situated in lush gardens, with on-street parking on your doorstep. 5 minute walk to WPI, 5 minute drive to city center and 15 mins to UMass Med. Furnished tastefully and simply with antiques and original art works; brand-new bathroom with shower; washer and dryer; fully-equipped kitchen. An ideal retreat or longer professional let - fast Eero mesh wifi network.

LocationValueTV

4.9 out of 5 average rating, 140 reviews

Top guest favorite

The bright living area features oversized windows that frame views of Spy Pond, allowing natural light to flood the space. Two armchairs and a round dining table with four chairs are arranged for comfort. A potted plant and decorative items enhance the inviting atmosphere.

Cottage in Arlington

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!

LocationFamilyCheck-in

4.95 out of 5 average rating, 85 reviews

Guest favorite

A charming red cottage is set against a backdrop of lush greenery. A golf cart is parked on the gravel driveway beside an outdoor canoe. The cottage features a sun-filled porch with multiple windows, inviting natural light into the space.

Cottage in Westford

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.

FamilyLocationCheck-in

4.93 out of 5 average rating, 43 reviews

Top guest favorite

Cottage in Stow

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

ValueLocationSkiing

4.97 out of 5 average rating, 248 reviews

Top guest favorite

A charming cottage with solar panels is reflected in the calm pond, surrounded by vibrant green lily pads. Pink water lilies float gently on the surface, enhancing the natural beauty of the setting. Lush trees create a serene backdrop, adding to the peaceful ambiance.

Cottage in Winchester

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.

LocationFamilyQuiet

4.95 out of 5 average rating, 86 reviews

Guest favorite

An open-concept living area features a cozy seating arrangement with a light blue sofa and woven chairs. Natural light fills the space from large windows. The kitchen, equipped with white cabinets, complements the wooden flooring. Decorative artwork adds character to the room.

Cottage in Westford

Lake Access & Pools: Sun-Soaked Westford Cottage!

Summer Village Community | Near State Parks | Steps to Beach Soak up the charm of an endless summer at this light-filled 2-bedroom, 1.5-bath vacation rental in Westford. Perfect for adventurous families or city folks craving a peaceful retreat, this inviting cottage sits just 35 miles from Boston — close enough for convenience yet far enough to feel like a true escape! Spend your days swimming in the pool, kayaking on the lake, playing pickleball, and exploring scenic trails. Book today!

LocationFamilyAir conditioning

5.0 out of 5 average rating, 5 reviews

Top guest favorite

The exterior of a gray cottage is surrounded by vibrant flowerbeds featuring purple and yellow blooms. A multicolored 'PEACE' banner hangs from the porch, which is framed by white railings and flanked by neatly trimmed shrubs. A stone wall borders the property.

Private room in Hopkinton

Cozy cottage in a quiet, lake community

My cottage resides in a lake community 25 miles west of Boston. It is a very short walk to a shared dock or beach. There are also wooded trails in my backyard for walking or trail running. It's very peaceful here. I have a wood burning stove and fire pit. Kayaks and inflatable SUP boards are available. I can’t wait to share my slice of paradise with you! During the Boston Marathon weekend there is 2 night minimum. I have a second bedroom that can be rented for a second or third person.

FamilyLocationBathroom

4.98 out of 5 average rating, 108 reviews

Cottage in Littleton

Romantic Peaceful Cozy and Adorable Cottage

Kick back and relax in this romantic, peaceful, stylish space.Cozy cottage house featuring full bedroom with a walking closet, kitchen, living room, dining room and bathroom. Very peaceful and laid-back atmosphere! Posh patio overlooking the pond with an outdoor table, and extra lounging chairs. Experience an outdoor setting on a slopped and rugged landscape with water view and access, and stairs to and from the dedicated parking spot. Absolutely No Smoking in the Cottage please.

Superhost

A serene view of Lost Lake shows a private dock extending into calm waters, with a small motorboat tied at its end. Lush green trees line the shore, providing a natural backdrop to the peaceful setting.

Cottage in Groton

Cozy, 2BR lake-side retreat and outdoor oasis

Our cozy, family friendly and completely remodeled lake house enjoys modern conveniences with private lake access and quick access to Boston (only 45 mins!). The vacation getaway is located on Lost Lake in beautiful Groton, MA bordering serene conservation land on 2 sides and facing a small private beach with dock. The location offers a balance of natural beauty with a convenience to amenities allowing you to get away from the fast paced city life but return at your leisure!

FamilyLocationGetting around

4.91 out of 5 average rating, 56 reviews

Top guest favorite

Cottage in Stow

Waters Edge

Take it easy at this unique and tranquil getaway on Lake Boone in a completely remodeled and reimagined space. Spend Summer days swimming, kayaking, or just floating in lounge chairs, all included. Amazing sunsets help transition to evening fire pits on the shore. In the Winter, bring ice skates or for fun on the lake, or just cozy up with a crackling fire. Waters Edge is an easy 40 minute drive into Boston, making it the perfect place to unwind after a day of sightseeing.

LocationFamilyDecor

4.9 out of 5 average rating, 10 reviews

Top guest favorite

A comfortable living area features a red armchair beside a coffee table, with a sofa in soft grey nearby. A brick fireplace is centered on the wall, while artwork and personal items are displayed on shelves. Natural light filters through sheer curtains.

Cottage in Andover

Cute Downtown Andover Cottage w/ Parking and Yard

Cute and classic. This home is one of the few mid-century cottages located in vibrant downtown Andover. A short walk to cafes, brewery, restaurants, Whole Foods and the Boston commuter rail. This bright 1,100 square foot cottage features two bedrooms and 1.5 baths, and includes ample driveway parking and a new deck looking over the large back yard. The home has a kitchen with full amenities and butcher block countertops. Fast wifi and smart TV help you work and play.

ValueLocationCheck-in

4.94 out of 5 average rating, 65 reviews

Guest favorite

Cottage in Westford

Just Chill'inn Cottage

Just Chill’inn is a beautiful 2-bedroom, 1 bath cottage including a 4-person golfcart in a family focused seasonal resort community. Enjoy a heated family pool, toddler pool, playground. A sandy beach on a lake. For you and your 18+ guests: additional adult heated pool, hot tub, and fitness center. Pickleball, tennis, basketball courts; recreation room with ping pong table; canoes, sunfish sailboats. Restaurant & bar with pool table at the lodge.

LocationFamilyAir conditioning

5.0 out of 5 average rating, 8 reviews