Vacation Rentals in Middlesex County: 3,700+ properties

Choose from 3,701 vacation rentals located in Middlesex County, Massachusetts. Top filters in Middlesex County include Internet / Wifi, Air conditioner, and TV. Prices range from $44 to $14,187 per night. Our most popular vacation rental types near Middlesex County are House and Hotel.

Top vacation rentals in Middlesex County

South Boston rental unit on top floor w/separate access, city views.

5.0

Outstanding(209 Reviews)

Condo

in South Boston

Spacious, Immaculate, Great Location

5 guests · 2 bedrooms · 1 bath

Pets allowed · Kitchen / Kitchenette · Air conditioner

This inviting Condo in Middlesex County can fit your needs for many types of vacations, at $158 per night.

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4.1

Excellent(2,445 Reviews)

Hotel

in Boston

4star

Hilton Boston Logan Airport

Garden · Pool · Pets allowed

Are you ready to indulge in a relaxing getaway? Our Hotel in Middlesex County has everything you need for a rejuvenating stay. Treat yourself to Hilton Boston Logan Airport's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

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4.1

Excellent(1,734 Reviews)

Hotel

in Boston

4star

Hyatt Regency Boston

Pets allowed · Air conditioner · Internet / Wifi

Looking to create some memories in Middlesex County? Look no further than our Hotel, Hyatt Regency Boston. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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5.0

Outstanding(200 Reviews)

Condo

in Malden

Near Boston Historic two-bedroom with Modern Amenities

7 guests · 2 bedrooms · 1 bath

Garden · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Middlesex County? Our Condo might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

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Search by amenity

Explore vacation rentals with the most popular amenities in Middlesex County

Vacation rentals with internet & wifi in Middlesex County

4.8

Outstanding(159 Reviews)

Docked boat

in Boston

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

6 guests · 1 bedroom · 1 bath

Pets allowed · Kitchen / Kitchenette · Air conditioner

The best choice in Middlesex County for Docked boat, for $160 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.8

Outstanding(185 Reviews)

House

in Leicester

Handcrafted New England Cape, Private Grounds, Perfect Family Retreat, Worc10min

10 guests · 5 bedrooms · 3 baths

Garden · Kitchen / Kitchenette · Air conditioner

House in Middlesex County, for $330 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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5.0

Outstanding(132 Reviews)

Condo

in Boston

Historic Home At Freedom Trail

4 guests · 1 bedroom · 1 bath

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for the perfect place to call home during your trip to Middlesex County? This Condo offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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3.9

Good(1,542 Reviews)

Hotel

in Boston

3star

DoubleTree by Hilton Hotel Boston Bayside

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Hotel for $96 in Middlesex County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Middlesex County

Middlesex County travel guide

Let us help you plan your perfect Middlesex County vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Middlesex County, and more.