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

Middlesex Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Middlesex holiday rentals

A two-story red building with a black front door, white trim, and a Christmas wreath.

1. The Cider Loft

The Cider Loft
Waterbury
8.4 out of 10, Very good, (31 reviews)
"It was centrally located for the time we were visiting the area."
United States
Rose
The price is HK$621
HK$1,562 total
includes taxes & fees
3 Nov - 4 Nov
The Cider Loft
A cozy cabin interior with wooden walls, a sofa, a rocking chair, a table, and a window with a view of greenery.

2. Brand New Cabin On Working Farm

Brand New Cabin On Working Farm
Northfield
9.8 out of 10, Exceptional, (38 reviews)
"This cabin was cute and cozy and very quiet. The hosts had thought of everything a guest might want or need. Wonderful stay."
United States
Kristen
The price is HK$882
HK$1,427 total
includes taxes & fees
30 Oct - 31 Oct
Brand New Cabin On Working Farm
A picnic area with a wooden bench, green chairs, and a fire pit.

3. 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 HK$875
HK$1,507 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1-bedroom loft apartment in lovely Duxbury
A bedroom with a bed, a white sofa, a wooden ceiling, and a painting on the wall.

4. Vintage farmhouse studio with on-site hot tub and mountain views

Vintage farmhouse studio with on-site hot tub and mountain views
Waterbury
9.0 out of 10, Wonderful, (35 reviews)
"Great spot, would stay again!"
United States
Kelly K.
The price is HK$823
HK$2,237 total
includes taxes & fees
1 Nov - 2 Nov
Vintage farmhouse studio with on-site hot tub and mountain views
A wooden cabin with a glass door and windows, a stone patio with lounge chairs, and a view of a sunset.

5. Countryside Cottage with Sauna and Fireplace

Countryside Cottage with Sauna and Fireplace
Berlin
10.0 out of 10, Exceptional, (5 reviews)
"Nice clean cottage with everything you could need. Easy check in and great communication"
United States
Justin F.
The price is HK$733
HK$2,043 total
includes taxes & fees
2 Nov - 3 Nov
Countryside Cottage with Sauna and Fireplace
A red barn with two white garage doors, a triangular roof, and a wreath on the front wall.

6. NEW! Studio Loft in Stowe Hollow

NEW! Studio Loft in Stowe Hollow
Stowe Hollow
10.0 out of 10, Exceptional, (216 reviews)
"Great stay"
United States
Daniel
The price is HK$784
HK$1,524 total
includes taxes & fees
3 Nov - 4 Nov
NEW! Studio Loft in Stowe Hollow
A house with a teal door, a mailbox, and a small garden with mulch, rocks, and a gnome statue.

7. 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)
"My 9 year old daughter loved being able to wake up and swim! The home was beautiful a d we had a great time."
United States
April A.
The price is HK$815
HK$1,668 total
includes taxes & fees
1 Nov - 2 Nov
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

8. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio
Warren
9.4 out of 10, Exceptional, (23 reviews)
"Enjoyable stay"
United States
Eric W.
The price is HK$404
HK$2,030 total
includes taxes & fees
28 Oct - 29 Oct
Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio
A two-story house with a red door, a covered porch, and a well-maintained lawn.

9. Stowe retreat with king bed and futon near Stowe Mountain Resort

Stowe retreat with king bed and futon near Stowe Mountain Resort
West Branch
8.8 out of 10, Excellent, (83 reviews)
"A very nicely designed space over a pub that was a little noisy on a Friday night stay. A Nice overall setting though ."
United States
peter
The price is HK$782
HK$2,789 total
includes taxes & fees
28 Oct - 29 Oct
Stowe retreat with king bed and futon near Stowe Mountain Resort
A room with a checkered bedspread, a patterned rug, and two black cylindrical objects.

10. One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!

One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
Barre
9.0 out of 10, Wonderful, (12 reviews)
"This was a comfortable location for our travels through New England."
United States
Bryan
The price is HK$776
HK$2,012 total
includes taxes & fees
1 Nov - 2 Nov
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
A neatly made bed with striped bedding, a beige throw blanket, and patterned pillows. There are two bedside lamps on wooden nightstands.

11. 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, (53 reviews)
"Excellent Location ! "
United States
Luke A.
The price is HK$1,360
HK$2,954 total
includes taxes & fees
29 Oct - 30 Oct
Go Skiing or Hiking from an Enchanting, Light-Filled Home
A spacious loft with a high ceiling, skylights, a living area with sofas, a dining table, and a staircase leading to an upper level.

12. Updated vintage farmhouse unit with on-site hot tub near Stowe

Updated vintage farmhouse unit with on-site hot tub near Stowe
Waterbury
9.0 out of 10, Wonderful, (39 reviews)
"The home was comfortable and convenient. The location was excellent."
United States
Amanda J.
The price is HK$947
HK$4,029 total
includes taxes & fees
28 Oct - 29 Oct
Updated vintage farmhouse unit with on-site hot tub near Stowe
A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

13. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

Out to Lunch trail ski-in/ski-out condo with balcony and heated pool
Warren
The price is HK$585
HK$2,383 total
includes taxes & fees
28 Oct - 29 Oct
Out to Lunch trail ski-in/ski-out condo with balcony and heated pool
A wooden deck with a view of a forested mountain range.

14. The Bridges condo with forested views, three pools and two saunas

The Bridges condo with forested views, three pools and two saunas
Warren
9.4 out of 10, Exceptional, (38 reviews)
"Nice view - Well-stocked kitchen - Nice pool and tennis courts "
United States
Michael L.
The price is HK$527
HK$2,778 total
includes taxes & fees
28 Oct - 29 Oct
The Bridges condo with forested views, three pools and two saunas
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and trees.

15. Light-filled Bridges condo overlooking the mountains, by the free shuttle

Light-filled Bridges condo overlooking the mountains, by the free shuttle
Warren
8.8 out of 10, Excellent, (20 reviews)
"Great location and amenities. "
United States
Scott H.
The price is HK$527
HK$2,488 total
includes taxes & fees
29 Oct - 30 Oct
Light-filled Bridges condo overlooking the mountains, by the free shuttle
A modern kitchen with a marble island, stainless steel appliances, and wooden stools.

16. 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, (59 reviews)
"We cancelled our reservation due to some cleanliness issues. The owner was grateful they were brought to his attention and he was very responsive. He indicated they will be addressed. Bedroom is very small. Better for children."
United States
Daniel
The price is HK$1,569
HK$3,997 total
includes taxes & fees
1 Nov - 2 Nov
Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain
A spacious living area with a wooden ceiling, a dining table with chairs, a sofa, a TV mounted on the wall, and a kitchen area with a sink and cabinets.

17. Luxury Living Space|Gorgeous Mountain Views

Luxury Living Space|Gorgeous Mountain Views
Stowe
9.6 out of 10, Exceptional, (44 reviews)
"There was an issue with the door lock and the host had it fixed within the day, so that was nice."
United States
Daniel
The price is HK$1,208
HK$2,258 total
includes taxes & fees
5 Nov - 6 Nov
Luxury Living Space|Gorgeous Mountain Views
Exterior view of the front of the cabin

18. Beautiful brand new cabin one minute from Sugarbush Resort

Beautiful brand new cabin one minute from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (24 reviews)
"Cool little place to stay"
United States
Dulan S.
Beautiful brand new cabin one minute from Sugarbush Resort
A modern kitchen with a dark countertop, two black bowls, a spoon, and a fork.

19. Charming 1-bedroom apartment in Jericho

Charming 1-bedroom apartment in Jericho
Jericho
9.4 out of 10, Exceptional, (25 reviews)
"This was such an amazing stay! This apartment was the perfect size for us for our stay! It was super clean, spacious, adorable, and the host offered so many amenities! We will definitely be staying here again next time we come to Vermont!"
United States
Ashley
The price is HK$847
HK$1,572 total
includes taxes & fees
28 Oct - 29 Oct
Charming 1-bedroom apartment in Jericho
A spacious living room with a wooden floor, a dining area with a table and chairs, a sofa with patterned cushions, and a television on a stand.

20. Spacious 2BR Loft · 15 Min to Stowe Mtn Resort · Quiet, Views & Dog Friendly

Spacious 2BR Loft · 15 Min to Stowe Mtn Resort · Quiet, Views & Dog Friendly
Morristown
9.2 out of 10, Wonderful, (52 reviews)
"Perfect spot for visiting Stowe and Vermont- host was very responsive."
United States
Emma S.
The price is HK$674
HK$1,888 total
includes taxes & fees
3 Nov - 4 Nov
Spacious 2BR Loft · 15 Min to Stowe Mtn Resort · Quiet, Views & Dog Friendly
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

von Trapp Family Lodge & Resort

von Trapp Family Lodge & Resort

8/10 Good
"Una propiedad con mucha historia y detalles. Habia una boda y practicamente todas las actividades estaban llenas, por lo que no pudimos hacer ninguna. El personal de maleteros no es muy simpatico. Pero el resto del personal es muy atento. la habitacion es comoda y limpia."
Yolanda 1-night trip
Posted 5 hours ago
von Trapp Family Lodge & Resort

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!

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.

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. Ben and Jerry's Factory and Vermont State House 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.