Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Middlesex vacation rentals

Waterslide

Smugglers' Notch Resort

Smugglers' Notch Resort
3.0 star property
Jeffersonville
7.8 out of 10, Good, (137 reviews)
"Very scenic location and great amenities at the resort"
United States
Divya
$393 nightly
The price is $426
Jun 7 - Jun 8
Total with taxes and fees
Smugglers' Notch Resort
Condo, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Orsinis At Mad House 3 Bedroom Condo by RedAwning

Orsinis At Mad House 3 Bedroom Condo by RedAwning
3.0 star property
Warren
$1,067 nightly
The price is $1,164
Jun 7 - Jun 8
Total with taxes and fees
Orsinis At Mad House 3 Bedroom Condo by RedAwning
Apartment, 2 Bedrooms | Private kitchen

Bridges Resort

Bridges Resort
2.0 star property
Warren
8.0 out of 10, Very Good, (25 reviews)
"close to the mountain"
United States
Brian Shultis
$164 nightly
The price is $178
Jun 7 - Jun 8
Total with taxes and fees
Bridges Resort
Condo, 3 Bedrooms | View from property

22 Village Run 3 Bedroom Condo by RedAwning

22 Village Run 3 Bedroom Condo by RedAwning
3.0 star property
Warren
$1,028 nightly
The price is $1,120
Jun 7 - Jun 8
Total with taxes and fees
22 Village Run 3 Bedroom Condo by RedAwning
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.
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Top Middlesex Hotel Reviews

Green Mountain Inn

Green Mountain Inn

10/10 Excellent
"Staying at The Green Mountain Inn was an absolute delight. Built in 1833, the inn has a timeless charm that you can feel the moment you walk in. The property is filled with beautiful historic photos—both of the inn itself and the surrounding town—which made it feel like we were stepping into a living piece of Vermont history. Our room was especially lovely. The décor was cozy and inviting, and the electric fireplace added the perfect touch of warmth and comfort. It made our mother‑daughter trip feel extra special and memorable. The town of Stowe was just as charming as the inn. Cute shops, walkable streets, and that quintessential Vermont atmosphere made exploring the area a joy. Overall, The Green Mountain Inn offered a unique, welcoming, and truly memorable stay. We couldn’t have chosen a better place for our trip."
Jennifer 1-night trip
Posted 4 hours ago
Green Mountain Inn

Find out more about Middlesex

Everything you need to know about Middlesex vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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's the top vacation rental in Middlesex?

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you: Visitors like this Middlesex vacation home rental. It offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Middlesex?

Expedia has 6 vacation rentals for your stay in Middlesex.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as The Cabot Annex Store, or get out into nature at a spot like Mad River Valley. Ben and Jerry's Factory and Vermont State House are a couple of places you'll find in the larger area.

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.