Cottage vacation rentals in Middlesex County

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!

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.

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.

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.

Just Chill'inn Cottage

Summer weeks are fully booked. September is available - beautiful - & pools and hot tub are open. Just Chill’inn is your 2-bedroom 1 bath cottage including a 4-person Golf Cart in a family focused seasonal resort community. Enjoy a heated family pool, toddler pool, playground. Pickleball, tennis courts. A sandy lake swimming beach. For your 18+ guests separate adult heated pool and hot tub, and fitness center. On weekends snack bar, restaurant and bar often with live entertainment and more.

White Pine Cottage - Cozy 3BR w/Fireplace in Woods

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.

Private Rm near Tufts/Harvard/MIT/MGH**

Our place is convenient to Harvard, Tufts, Lesley MGH & MIT It is close to the RED Line "T" stations (Alewife + Davis) as well as the bus #77 stop. You’ll love our place because of the safe, quiet neighborhood, the comfy queen sized Kingsdown mattress with lots of fluffy pillows, a down comforter, a desk, a moon pod, and a skylight. In addition you will be helping two grandparents save money for flights to visit their grandchildren in Italy & Canada! NOTE: Please no dog allergies/phobias.

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!

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.

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!

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.

Willow Creek Cottage

Set up your home-away-from-home-office at Willow Creek Cottage. Close access to Massachusetts' business corridors. Conveniently located for the i90, 495 and biohubs in the Boston Metrowest. Walking distance (1 mile) to Southborough MBTA station. Fully equipped kitchen with washer & dryer. Off street parking. Level 2 CCS car charger available upon request. Idyllic location on a small farm. Forest trails nearby at Hopkinton State Park. Strictly no pets. Non-smokers only