Owner Direct Vacation
Rentals in Middlesex County
The Best Owner Direct Vacation Rentals in Middlesex County. Explore thousands of vacation home rentals, large cabins, and villas near Middlesex County
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Explore the Best Middlesex County Vacation Homes
Looking for the perfect place to stay in Middlesex County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Middlesex County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Middlesex County
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Popular Neighborhoods for Middlesex County Vacation Rentals
What are the best areas to stay in Middlesex County
Discover the top neighborhoods in Middlesex County and choose a place that suits your stay.
Cambridge
Cambridge VACATION RENTALSSomerville
Somerville VACATION RENTALSArefth
Arefth VACATION RENTALSEast Cambridge
East Cambridge VACATION RENTALSEverett
Everett VACATION RENTALSCentral Square
Central Square VACATION RENTALSThe Port
The Port VACATION RENTALSWaltham
Waltham VACATION RENTALSMedford
Medford VACATION RENTALSWoburn
Woburn VACATION RENTALSWinter Hill
Winter Hill VACATION RENTALSThe Lanes
The Lanes VACATION RENTALSMonday Apr 20
Middlesex County, Massachusetts







Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Middlesex County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Middlesex County
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How to Reserve Your Middlesex County Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
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Use filters for location, amenities, and budget.
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BOOK SECURELY
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Middlesex County Vacation Rental FAQs
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlesex County:
- Near Boston Historic two-bedroom with Modern Amenities
- Fun, Family Friendly Restored Fire House 2 Bedroom Apt
- 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
- 3 BR/3 BATH in Historic Home Mins from Kendall Sq , MIT, Harvard, Boston.
- The Inn at Newton Highlands, boutique apartment-hotel
- The Inn at Newton Highlands, boutique apartment-hotel
- Wonderfully renovated family-friendly home located near Boston and Lexington
- Super Family-Friendly! Spacious, cozy home base - close to Boston & Salem MA!
- A Village Bed and Breakfast
- Mid Century in Historic Lexington
There are 71 vacation rentals with private pools near Middlesex County. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Middlesex County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlesex County:
Currently, the total number of properties listed in 2026 is over 2294 in the Middlesex County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Middlesex County.