Middlesex Vacation Rentals

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Vacation 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 CA $395
CA $549 total
includes taxes & fees
Sep 20 - Sep 21
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 CA $210
CA $280 total
includes taxes & fees
Aug 26 - Aug 27
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, (67)
"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 CA $201
CA $472 total
includes taxes & fees
Aug 27 - Aug 28
Modern, Comfy & Clean Condo at Mountainside - Pool/HotTub, WIFI, on Mtn R

The Annex

9.6 out of 10, Exceptional, (57)
"Great location to enjoy Stowe"
The price is CA $137
CA $331 total
includes taxes & fees
Sep 3 - Sep 4
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, (20)
"It is not luxurious, but is absolutely unique and fun! We loved it!"
The price is CA $166
CA $218 total
includes taxes & fees
Aug 26 - Aug 27
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, (28)
"Beautiful house, clean, fabulous grounds, excellent location!"
The price is CA $243
CA $625 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $104
CA $384 total
includes taxes & fees
Aug 24 - Aug 25
Great Value in Stowe w/kitchenette, free WiFi - near trails

Modern Tiny House w/hot tub & river near Stowe

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great place to stay to access a few different Vermont destinations. The tiny home was a perfect size for the two of us."
Modern Tiny House w/hot tub & river near 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 CA $250
CA $451 total
includes taxes & fees
Aug 26 - Aug 27
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, (76)
"Clean, as described, perfect experience"
The price is CA $137
CA $394 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $258
CA $529 total
includes taxes & fees
Sep 14 - Sep 15
Romantic Cabin: Pet Friendly, Close to Town, Wood stove, 1 Bdrm + Loft

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 CA $233
CA $298 total
includes taxes & fees
Aug 25 - Aug 26
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)
"Unfortunate rodent problem, but otherwise a great place with all the amenities you could want on a ski break. Owner is in the process of fixing."
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, (21)
"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 CA $165
CA $365 total
includes taxes & fees
Aug 24 - Aug 25
Artist Studio

Mountain Condo w/ Views: Near Hiking & Biking!

9.0 out of 10, Wonderful, (24)
"The house was very clean and great location to Stowe. "
Mountain Condo w/ Views: Near Hiking & Biking!

To Camp or To Glamp?

The price is CA $104
CA $179 total
includes taxes & fees
Aug 26 - Aug 27
To Camp or To Glamp?

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (149)
"Perfect retreat inside a charming cabin for a ski getaway. Enjoy memorable family moments. "
The price is CA $333
CA $637 total
includes taxes & fees
Sep 10 - Sep 11
Stetson Hollow Cabin by Stetson Brook
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

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.

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 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.