
Vacation rentals in Middlesex County
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Top-rated vacation rentals in Middlesex County
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All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

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.

Entire Apartment in Newton, Close to Boston!
Come stay in this comfortable one bedroom apartment with large open space living room, kitchen area, bathroom, Wi-Fi, parking, and a private entrance onto a gorgeous backyard garden. Centrally located in a quiet neighborhood equidistant from Moody St. in Waltham and West Newton Sq. -- a 15 minute walk from excellent restaurants and an independent movie theater in both directions. Two dance studios with regular weekend dances nearby. To protect guests with allergies, no pets allowed.

Comfy-Spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Charming 1 BR private entrance apt commuters dream
Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Water front cabin-like guest suite on a quiet pond
Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Couples Retreat - Apt in Charming Colonial Home
Newly renovated, open concept apartment in a private home located on a quiet residential street. Single, queen-sized adjustable bed, steam shower, and oversized bubble jet tub make this an ideal retreat for stress free relaxation. Includes off-street parking, full-size washer and dryer, and the use of both front and rear porches with seating in season. This apartment is great for couples or individuals looking to relax and get a break from their busy lives.

Farm stay in a Historic Ski Lodge turned Barn
Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Mema's Place --Lovely apartment in private home
This private apartment in a lovely home in historic Concord, Massachusetts features one bedroom with queen bed, living room, kitchen, bathroom, and porch. Your apartment is locked off from the rest of the home and you have your own entrance. We are within 4 miles of Concord Academy, Middlesex School, the North Bridge, Sleepy Hollow Cemetery (where Alcott, Thoreau, Emerson, and Hawthorne are buried).

Your Cozy 1 BR Apt & Relaxing Retreat
Romantic Luxury Getaway • Private Jacuzzi • Fire Pit • BBQ • Near Boston Escape to this cozy 1-bed retreat made for relaxation and special moments. Enjoy your private jacuzzi, unwind by the fire pit, and grill on the BBQ for the perfect night in. Located in a quiet area just minutes from Boston, restaurants, and shopping — the ideal spot for couples or a peaceful weekend escape.
Popular amenities for Middlesex County vacation rentals
Other great vacation rentals in Middlesex County

Sunny Peaceful Groton Apartment with Deck

The Enchanted Willow Storybook Boston Escape 3BDR

Spacious & Pet-Friendly Modern Home in Charlestown

Studio Apartment in Sudbury

Elegant Guest suite Wellesley

Spacious 3BD Ranch With Fenced-In Yard

Historical New England retreat

Millside Maynard: Walkable 2BR/Flex Office Apt
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Boston Seaport
- New England Aquarium
- Freedom Trail
- MIT Museum
- Monadnock State Park
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Gillette Stadium
- Crane Beach
- Quincy Market
- Duxbury Beach
- Museum of Fine Arts
- North Hampton Beach
- Prudential Center
- Roxbury Crossing Station
- Boston Children's Museum
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