An aerial view of a rural area with autumn-colored trees, a river, and scattered houses.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Middlesex holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain

Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain
Waterbury Village Historic District
8.8 out of 10, Excellent, (58 reviews)
"Space was clean and surprisingly spacious. Fantastic location. Enjoyed spending some time on your lovely front porch as well. Thank you!"
United States
Eric H.
The price is €488
includes taxes & fees
20 Sept - 21 Sept
Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain
Outdoor dining

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

Mountain Cabin Bordering State Park. Hiking, Private. Special Place, Great View!
Duxbury
10.0 out of 10, Exceptional, (43 reviews)
"Quiet little getaway."
United States
Kim P.
The price is €407
includes taxes & fees
26 Sept - 27 Sept
Mountain Cabin Bordering State Park. Hiking, Private. Special Place, Great View!
Smart TV

3. Brand New Cabin On Working Farm

Brand New Cabin On Working Farm
Northfield
9.8 out of 10, Exceptional, (31 reviews)
"The property really is on a working farm. Upon first arrival we were greeted by a flock of ducks. The farm dogs treated us the second day when we returned from dinner. We were able to visit the sheep, cow and chickens during the daylight hours. Step out the front door during the day to enjoy the Mountain View or at night and enjoy the stary sky of Vermont. The inside is brand new and in pristine condition, with lots of space. A full working kitchen, dining table, love seat and entertainment...
United States
Thomas
The price is €161
includes taxes & fees
17 Sept - 18 Sept
Brand New Cabin On Working Farm
Property grounds

4. Cozy 1-bedroom loft apartment in lovely Duxbury

Cozy 1-bedroom loft apartment in lovely Duxbury
Duxbury
9.8 out of 10, Exceptional, (25 reviews)
"Place was super cute and they let me bring my dog!"
United States
Sharyn and Kiersten v.
The price is €226
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-bedroom loft apartment in lovely Duxbury
Terrace/patio

5. Artful Lodging 1st Fl'r 2 Bedroom Apt in Civil War Infirmary Home Montpelier VT

Artful Lodging 1st Fl'r 2 Bedroom Apt in Civil War Infirmary Home Montpelier VT
Montpelier
9.6 out of 10, Exceptional, (26 reviews)
"The place was so lovely! We were only there for an overnight so we didn't cook or use any of the other amenities but everything was great, and Beth was extremely kind and helpful with suggesting places for us to do and things to see. "
United States
Douglas N.
The price is €249
includes taxes & fees
22 Sept - 23 Sept
Artful Lodging 1st Fl'r 2 Bedroom Apt in Civil War Infirmary Home Montpelier VT
Exterior

6. The Cider Loft

The Cider Loft
Waterbury
8.4 out of 10, Very good, (23 reviews)
"The location was very close to Stowe Mountain, which made our stay very convenient to us. "
United States
Shain G.
The price is €240
includes taxes & fees
21 Sept - 22 Sept
The Cider Loft
2 bedrooms, travel cot, WiFi, bed sheets

7. Go Skiing or Hiking from an Enchanting, Light-Filled Home

Go Skiing or Hiking from an Enchanting, Light-Filled Home
Waitsfield
9.8 out of 10, Exceptional, (50 reviews)
"Excellent Location ! "
United States
Luke A.
The price is €321
includes taxes & fees
17 Sept - 18 Sept
Go Skiing or Hiking from an Enchanting, Light-Filled Home
Waterslide

8. Smugglers' Notch Resort

Smugglers' Notch Resort
3.0 star property
Jeffersonville
7.8 out of 10, Good, (138 reviews)
"Very scenic location and great amenities at the resort"
United States
Divya
The price is €249
includes taxes & fees
15 Oct - 16 Oct
Smugglers' Notch Resort
Iron/ironing board, free WiFi, bed sheets

9. Vintage farmhouse studio with on-site hot tub - near year-round recreation

Vintage farmhouse studio with on-site hot tub - near year-round recreation
Waterbury
9.0 out of 10, Wonderful, (35 reviews)
"Great spot, would stay again!"
United States
Kelly K.
Vintage farmhouse studio with on-site hot tub - near year-round recreation
TV, offices

10. Luxury Living Space|Gorgeous Mountain Views

Luxury Living Space|Gorgeous Mountain Views
Stowe
9.8 out of 10, Exceptional, (40 reviews)
"Great stay very private and extremely clean Thank you ! Would definitely book again"
United States
Jennifer H.
The price is €315
includes taxes & fees
27 Sept - 28 Sept
Luxury Living Space|Gorgeous Mountain Views
Interior

11. Two Bedroom Apt in Barre VT!

Two Bedroom Apt in Barre VT!
Barre
9.6 out of 10, Exceptional, (12 reviews)
"Very attentive owner. Property in excellent condition. My family will be back!"
United States
Tom G.
The price is €340
includes taxes & fees
29 Sept - 30 Sept
Two Bedroom Apt in Barre VT!
Smart TV, offices

12. Beautiful Family Home Central to Mad River Valley

Beautiful Family Home Central to Mad River Valley
Waitsfield
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic house and property in a beautiful area. We had a great stay and everything was wonderful."
United States
Greg L.
The price is €696
includes taxes & fees
24 Sept - 25 Sept
Beautiful Family Home Central to Mad River Valley
Interior

13. Renovated Condo in Luxury Neighborhood

Renovated Condo in Luxury Neighborhood
Stowe
9.6 out of 10, Exceptional, (33 reviews)
"Clean, easy check in and good communication "
United States
Patti C.
The price is €258
includes taxes & fees
28 Sept - 29 Sept
Renovated Condo in Luxury Neighborhood
Smart TV

14. 1830 Enchanting, Light-Filled Farmhouse Apartment

1830 Enchanting, Light-Filled Farmhouse Apartment
Waitsfield
10.0 out of 10, Exceptional, (41 reviews)
"We skied at Sugarbush. The location was great. Very nice place to stay!"
United States
Laurie K.
The price is €316
includes taxes & fees
17 Sept - 18 Sept
1830 Enchanting, Light-Filled Farmhouse Apartment
Exterior

15. Modern Condo Surrounded by Nature I Heart of Stowe

Modern Condo Surrounded by Nature I Heart of Stowe
Stowe
9.4 out of 10, Exceptional, (28 reviews)
"Fabulous location for a home base for a trip to Stowe!"
United States
Lindsey C.
The price is €285
includes taxes & fees
27 Sept - 28 Sept
Modern Condo Surrounded by Nature I Heart of Stowe
Smart TV

16. Stowe Lofts- 2-bedroom condo, peaceful, 5 min to Stowe, Ask about pet policy

Stowe Lofts- 2-bedroom condo, peaceful, 5 min to Stowe, Ask about pet policy
Morristown
9.2 out of 10, Wonderful, (49 reviews)
"Perfect spot for visiting Stowe and Vermont- host was very responsive."
United States
Emma S.
The price is €259
includes taxes & fees
17 Sept - 18 Sept
Stowe Lofts- 2-bedroom condo, peaceful, 5 min to Stowe, Ask about pet policy
Apartment, 2 Bedrooms | Private kitchen

17. Bridges Resort

Bridges Resort
2.0 star property
Warren
8.2 out of 10, Very good, (30 reviews)
"close to the mountain"
United States
Brian Shultis
The price is €344
includes taxes & fees
21 Sept - 22 Sept
Bridges Resort
Exterior

18. Condo at Stowe`s Toll House | Ski-in/Ski-out!

Condo at Stowe`s Toll House | Ski-in/Ski-out!
Stowe
9.8 out of 10, Exceptional, (28 reviews)
"Great location, clean home perfect for our family"
United States
Stephanie D.
The price is €555
includes taxes & fees
17 Sept - 18 Sept
Condo at Stowe`s Toll House | Ski-in/Ski-out!
Property grounds

19. Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich

Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Williamstown
10.0 out of 10, Exceptional, (61 reviews)
"Very peaceful setting! Love the chairs on the back deck, looking out onto the yard. Everything was clean and well kept. Check-in was effortless. I would definitely stay here again."
United States
Heather
The price is €178
includes taxes & fees
28 Sept - 29 Sept
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Terrace/patio

20. Ski-in Ski-out, Chic, Cozy & Fun, Great Location Stowe!

Ski-in Ski-out, Chic, Cozy & Fun, Great Location Stowe!
Stowe
10.0 out of 10, Exceptional, (66 reviews)
"Great stay, comfortable beds, very clean. Great space for 2 families with young kids. "
United States
Lexi P.
The price is €716
includes taxes & fees
18 Sept - 19 Sept
Ski-in Ski-out, Chic, Cozy & Fun, Great Location Stowe!
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

Outbound Stowe

Outbound Stowe

10/10 Excellent
"Only complaint is there needs to be a shade over the window in the bathroom as you can see inside it. Other than that everything else was perfect!"
Linda 1-night trip
Posted 3 hours ago
Outbound Stowe

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.

How many holiday rentals are there in Middlesex?

Expedia has 3 holiday rentals for your stay in Middlesex.

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.