Cottage holiday 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 favourite

Cottage in Arlington

5 out of 5 average rating, 44 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!

Cottage in Westford

4.67 out of 5 average rating, 3 reviews

Waterfront Cottage in Summer Village w/ Grill

Escape to a peaceful retreat at this waterfront 2-bed, 1-bath Westford vacation rental. Spend your days kayaking and paddle boarding around the pond, or go for a hike at Lowell Heritage State Park! After your adventures, check out the community perks, including family-friendly pools, an adults-only pool with a hot tub, sports courts, and a large sandy beach. Later on, fire up the gas grill for a BBQ, then sit back and unwind by the water while taking in the serene views of the surrounding area!

Top guest favourite

Cottage in Worcester

4.89 out of 5 average rating, 125 reviews

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.

Superhost

Cottage in Westford

4.92 out of 5 average rating, 39 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 favourite

Cottage in Winchester

4.96 out of 5 average rating, 72 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 Westford

5 out of 5 average rating, 5 reviews

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.

Guest favourite

Private room in Cambridge

4.93 out of 5 average rating, 45 reviews

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.

Superhost

Cottage in Groton

4.92 out of 5 average rating, 49 reviews

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!

Top guest favourite

Cottage in Andover

4.91 out of 5 average rating, 43 reviews

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.

Guest favourite

Cottage in Southborough

4.93 out of 5 average rating, 44 reviews

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

Cottage in Littleton

New place to stay

Peaceful Cozy Adorable Cottage

Kick back and relax in this calm, 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 stairs to and from the dedicated parking spot.

Cottage in Concord

4.65 out of 5 average rating, 55 reviews

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.