Holiday Rentals in Middlesex

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Holiday Rentals in Middlesex

Smugglers' Notch Resort

3.0 star property
8.0 out of 10, Very good, (115)
"Great place to spend time with family and friends. Lots of options to keep everyone entertained (tennis court, indoor kids play area, several pools including heated one, volleyball and basketball court, small coffee shop and restaurant and tons of activities prepared by hotel staff). Want to come back!"
The price is €350
includes taxes & fees
28 Sept - 29 Sept
Smugglers' Notch Resort

Bridges Resort

3.5 star property
8.0 out of 10, Very good, (12)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
The price is €172
includes taxes & fees
2 Sept - 3 Sept
Bridges Resort

Stowe Cabins in the Woods

2.5 star property
8.8 out of 10, Excellent, (294)
"We stay here sometimes a couple times a year always reliable, always a great place to stay. The cabins are a little dated. But you are staying in a cabin in the woods. Definitely stay here again which I plan on doing in the future. So many things to do in Waterberry and in Stowe. This place a must stay. "
Stowe Cabins in the Woods

Modern, Comfy & Clean Condo at Mountainside - Pool/HotTub, WIFI, on Mtn R

9.2 out of 10, Wonderful, (69)
"Stayed for a single overnight to do some skiing at Jay and Stowe. Great property, clean, charming, easy rental. Would stay again!"
The price is €330
includes taxes & fees
31 Aug - 1 Sept
Modern, Comfy & Clean Condo at Mountainside - Pool/HotTub, WIFI, on Mtn R

The Annex

9.6 out of 10, Exceptional, (58)
"Great location to enjoy Stowe"
The price is €210
includes taxes & fees
3 Sept - 4 Sept
The Annex

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (21)
"Pleasant hosts. My daughter milked s goat! Great night’s sleep."
The price is €170
includes taxes & fees
4 Sept - 5 Sept
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Beautiful Secluded Maple Corner Cottage Near Curtis Pond! Ski, Swim, Hike, Bike!

9.8 out of 10, Exceptional, (29)
"Beautiful house, clean, fabulous grounds, excellent location!"
The price is €380
includes taxes & fees
2 Sept - 3 Sept
Beautiful Secluded Maple Corner Cottage Near Curtis Pond! Ski, Swim, Hike, Bike!

Great Value in Stowe w/kitchenette, free WiFi - near trails

7.8 out of 10, Good, (53)
"We enjoyed our time. It was close to the mountain and very homey. Would stay again! Definitely recommend!"
The price is €236
includes taxes & fees
1 Sept - 2 Sept
Great Value in Stowe w/kitchenette, free WiFi - near trails

Griffin Chalet 2 ~ mile to Stowe

8.0 out of 10, Very good, (4)
"Very comfortable; owners really accommodating and welcoming. Highly Recommend!"
The price is €365
includes taxes & fees
2 Sept - 3 Sept
Griffin Chalet 2 ~ mile to Stowe

Beautiful Riverfront Townhome, Steps to Historic Downtown Stowe

10.0 out of 10, Exceptional, (72)
"Location is a short ride to Stowe, which was nice, and walking distance to all the shops in town. If you don't feel like cooking, the local market is right across the parking lot and has lots of prepared foods ready to go."
Beautiful Riverfront Townhome, Steps to Historic Downtown Stowe

Fully Renovated Condo in Heart of Stowe

9.2 out of 10, Wonderful, (19)
"A perfect spot for me, my husband, son and two granddaughters to enjoy an end-of-season ski trip to Stowe! "
The price is €287
includes taxes & fees
2 Sept - 3 Sept
Fully Renovated Condo in Heart of Stowe

Radiant dog-friendly getaway w/a prime location near Stowe Mountain Resort

8.8 out of 10, Excellent, (77)
"Clean, as described, perfect experience"
The price is €238
includes taxes & fees
1 Sept - 2 Sept
Radiant dog-friendly getaway w/a prime location near Stowe Mountain Resort

Romantic Cabin: Pet Friendly, Close to Town, Wood stove, 1 Bdrm + Loft

10.0 out of 10, Exceptional, (213)
"This is our third time staying at Goldilocks Cabin for a ski vacation. The location and amenities are perfect!"
The price is €324
includes taxes & fees
14 Sept - 15 Sept
Romantic Cabin: Pet Friendly, Close to Town, Wood stove, 1 Bdrm + Loft

Gorgeous Home with Free WiFi, Electric Fireplace, & Shared Pool/Hot Tub

9.0 out of 10, Wonderful, (51)
"Clean, great location."
The price is €313
includes taxes & fees
8 Sept - 9 Sept
Gorgeous Home with Free WiFi, Electric Fireplace, & Shared Pool/Hot Tub

Mountain Cabin Bordering State Park. Hiking, Private. Special Place, Great View!

10.0 out of 10, Exceptional, (17)
"Comfortable, cozy, not kitschy, with nice appliances and furnishings. The location is beautiful and serene - heavily forested, with a babbling brook running alongside the property. The place is clean and well-kept. The shops and restaurants in Waterbury are a short drive away. My only quibble with the property is with the upstairs beds, which made a horrible racket when you turned or shifted your weight. "
Mountain Cabin Bordering State Park. Hiking, Private. Special Place, Great View!

Luxury Living Space|Gorgeous Mountain Views

9.8 out of 10, Exceptional, (20)
"Nice place up the hill from Stowe village. 15 minute drive to the ski hill."
The price is €275
includes taxes & fees
1 Sept - 2 Sept
Luxury Living Space|Gorgeous Mountain Views

Lovely secluded cabin on VAST trail in VT's "Land of Lakes and Ponds"

10.0 out of 10, Exceptional, (94)
"This place is amazing. The cabin sitting in its natural habit is breathtaking. The cabin was welcoming and comfortable with all the amenities we needed plus more. This is by far a favorite place to stay. Would like to spend more time here on our next trip"
The price is €209
includes taxes & fees
15 Sept - 16 Sept
Lovely secluded cabin on VAST trail in VT's "Land of Lakes and Ponds"

Great location, sleeps 10 , close to mountain/town , hot tub, 3 full baths

9.6 out of 10, Exceptional, (243)
"Second time staying here and loved it!!! Well equipped kitchen and plenty of beds "
Great location, sleeps 10 , close to mountain/town , hot tub, 3 full baths

Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

10.0 out of 10, Exceptional, (22)
"Our stay at this beautiful property was just the reset I needed. It was blissfully quiet and we enjoyed evenings out by the fire. "
Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

Artist Studio

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay. It was nice to walk to restaurants and stores."
The price is €231
includes taxes & fees
1 Sept - 2 Sept
Artist Studio
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

Find out more about Middlesex

Find out more about Middlesex

Everything you need to know about Middlesex holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesex holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex holiday rentals we have selected for you start as low as €170 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

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

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. Stowe Mountain Resort and Ben and Jerry's Factory are a couple of places you'll find in the wider area.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.