Choose from 3,540 vacation rentals located in Middlesex County, Massachusetts. Top filters in Middlesex County include Air conditioner, Internet / Wifi, and TV. Prices range from $44 to $12,112 per night. Our most popular vacation rental types near Middlesex County are House and Hotel.

Top vacation rentals in Middlesex County

Property view
5.0
Outstanding(188 Reviews)
Docked boat
 in Boston
\"Travelers' Choice Award\" Green Turtle I Houseboat in Boston Harbor!
2 guests · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Middlesex County? Look no further than our Docked boat, \"Travelers' Choice Award\" Green Turtle I Houseboat in Boston Harbor! . Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Exterior
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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Property view
4.3
Excellent(1,085 Reviews)
Hotel
 in Boston
5star
InterContinental Boston, an IHG Hotel
Garden · Pool · Pets allowed

The best choice in Middlesex County for Hotel, for $103 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.1
Excellent(1,284 Reviews)
Hotel
 in Andover
3star
La Quinta by Wyndham Boston-Andover
Pool · Pets allowed · Kitchen / Kitchenette

Hotel in Middlesex County, for $75 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Vacation rentals with air conditioning in Middlesex County

Marina
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 $200 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
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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Property view
4.1
Excellent(290 Reviews)
Hotel
 in Cambridge
4star
The Charles Hotel in Harvard Square
Garden · Pets allowed · Air conditioner

Looking for a Hotel in Middlesex County, this Hotel for $103 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Property view
4.0
Good(2,133 Reviews)
Inn
 in Boston
Copley House
Pets allowed · Kitchen / Kitchenette · Air conditioner

Inn in Middlesex County, for $78 per night is great for your next (business stay, family stays, 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.

Frequently asked questions

What is the price range for rentals in Middlesex County?

Vacation rentals in Middlesex County have a price range between $44-$12,112. The average price for rentals in Middlesex County is $172 per night.

What are the top travel destinations in Middlesex County

Boston, Cambridge, and South Boston are the top three destinations to travel in Middlesex County.

How many cities have available rentals in Middlesex County?

There are 20 destinations with available rentals in Middlesex County.

Travel inspiration

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