Photo by The Curious Zephyr

Middlesex Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Middlesex vacation rentals

View from room
Smugglers' Notch Resort

Condo resort in Jeffersonville

Smugglers' Notch Resort
3.0 star property
8.0 out of 10, Very Good, (135)
"Very scenic location and great amenities at the resort"
United States
Divya
The price is P16,772
P23,279 total
includes taxes & fees
Jan 31 - Feb 1, 2026
Smugglers' Notch Resort
Private kitchen
Bridges Resort

Condo resort in Warren

Bridges Resort
3.5 star property
8.2 out of 10, Very Good, (16)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
The price is P10,471
P13,918 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bridges Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex Hotel Reviews

Innsbruck Inn at Stowe

Innsbruck Inn at Stowe

10/10 Excellent
"Breakfast, service, room was nice and clean"
Lori 4-night trip
Posted 2 days ago
Innsbruck Inn at Stowe

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex
  • Use the map to find apartments and other holiday homes in the Middlesex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex while they last

Look no further and take a look at our great range of rental properties in Middlesex!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Middlesex?

Yes, we offer vacation rentals close to the most popular attractions in Middlesex, or you can choose a more remote option if you're looking for relaxation.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Vermont Ski Museum, or get out into nature at a spot like Mad River Valley. Other popular places to visit in the area include Sugarbush Ski Resort and Stowe Mountain Resort.

What are vacation rentals like in Middlesex?

Vacation rentals are privately owned properties you can reserve for several days or longer in Middlesex. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.