Photo by The Curious Zephyr

Middlesex Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Middlesex holiday rentals

View from room
Smugglers' Notch Resort

Smugglers' Notch Resort

Smugglers' Notch Resort
3.0 star property
Jeffersonville
8.0 out of 10, Very good, (135)
"Very scenic location and great amenities at the resort"
United States
Divya
The price is HK$2,219
HK$3,079 total
includes taxes & fees
29 Jan - 30 Jan 2026
Smugglers' Notch Resort
Property grounds
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
2.0 star property
Chelsea
10.0 out of 10, Exceptional, (38)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is HK$1,166
HK$1,498 total
includes taxes & fees
4 Jan - 5 Jan 2026
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds
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

Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Williamstown
10.0 out of 10, Exceptional, (54)
"It was a great central location to everything that we wanted to see and do in Vermont!"
United States
Tanner H.
The price is HK$693
HK$1,472 total
includes taxes & fees
8 Jan - 9 Jan 2026
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Exterior
Secluded retreat in the trees

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (38)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is HK$980
HK$1,828 total
includes taxes & fees
5 Jan - 6 Jan 2026
Secluded retreat in the trees
Interior
Gorgeous Home with Free WiFi, Electric Fireplace, & Shared Pool/Hot Tub

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

Gorgeous Home with Free WiFi, Electric Fireplace, & Shared Pool/Hot Tub
West Branch
9.0 out of 10, Wonderful, (60)
"Perfect stay for our family of 4. Enjoyed breathtaking views of the mountains from both the balcony and cozy family room. Would definitely stay again."
United States
Stacy D.
The price is HK$615
HK$3,070 total
includes taxes & fees
6 Jan - 7 Jan 2026
Gorgeous Home with Free WiFi, Electric Fireplace, & Shared Pool/Hot Tub
1 bedroom, iron/ironing board, travel cot, free WiFi
Cozy Cabin Retreat

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (33)
"A wonderful cabin. I need to come back sometime."
United States
Fletcher F.
The price is HK$917
HK$1,655 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cabin Retreat
Outdoor dining
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony
Warren
8.4 out of 10, Very good, (74)
"Perfect summer getaways! The condo was comfortable and in a great location. The pools and rec center were also so much fun. Looking forward to coming back next year."
United States
Christine P.
The price is HK$490
HK$1,691 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony
Fridge, microwave, oven, stovetop
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!

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
8.8 out of 10, Excellent, (9)
"Excellent stay, clean, comfortable, great little extras. Wish a few windows had screens for fresh air at night. "
United States
Sean
The price is HK$770
HK$1,977 total
includes taxes & fees
4 Jan - 5 Jan 2026
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Vintage farmhouse studio with on-site hot tub - near year-round recreation

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, (30)
"The bed was super comfy!"
United States
Casey J.
The price is HK$700
HK$2,104 total
includes taxes & fees
15 Jan - 16 Jan 2026
Vintage farmhouse studio with on-site hot tub - near year-round recreation
Exterior
Ski getaway near the slopes with private balcony & mountain views

Ski getaway near the slopes with private balcony & mountain views

Ski getaway near the slopes with private balcony & mountain views
Warren
8.8 out of 10, Excellent, (22)
"Ideally located for any season "
United States
Alison M.
The price is HK$638
HK$2,850 total
includes taxes & fees
4 Jan - 5 Jan 2026
Ski getaway near the slopes with private balcony & mountain views
Fridge, microwave, oven, stovetop
Stowe Lofts-Cozy 2-bedroom condo, peaceful, 5 minutes to Stowe, Fast WiFi

Stowe Lofts-Cozy 2-bedroom condo, peaceful, 5 minutes to Stowe, Fast WiFi

Stowe Lofts-Cozy 2-bedroom condo, peaceful, 5 minutes to Stowe, Fast WiFi
2.0 star property
Morristown
9.2 out of 10, Wonderful, (35)
"Very clean and updated with comfortable beds."
United States
Laurie M.
The price is HK$1,574
HK$2,825 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stowe Lofts-Cozy 2-bedroom condo, peaceful, 5 minutes to Stowe, Fast WiFi
Property grounds
Inviting condo near skiing and golf, with fireplace and deck

Inviting condo near skiing and golf, with fireplace and deck

Inviting condo near skiing and golf, with fireplace and deck
Warren
8.8 out of 10, Excellent, (10)
"Location, close to everything"
United States
Dave D.
The price is HK$669
HK$2,079 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inviting condo near skiing and golf, with fireplace and deck
Fridge, microwave, oven, stovetop
Welcoming studio w/ full kitchen, futon, partial AC - close to skiing & hiking

Welcoming studio w/ full kitchen, futon, partial AC - close to skiing & hiking

Welcoming studio w/ full kitchen, futon, partial AC - close to skiing & hiking
West Branch
8.2 out of 10, Very good, (57)
"Incredible location to explore! Had an absolute blast in the area, highly recommended!"
United States
Michael M.
The price is HK$833
HK$2,542 total
includes taxes & fees
4 Jan - 5 Jan 2026
Welcoming studio w/ full kitchen, futon, partial AC - close to skiing & hiking
Fridge, oven, stovetop, dishwasher
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Warren
9.2 out of 10, Wonderful, (18)
"Great place"
United States
Jonathan M.
The price is HK$498
HK$2,366 total
includes taxes & fees
12 Jan - 13 Jan 2026
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Private kitchen
Bridges Resort

Bridges Resort

Bridges Resort
3.5 star property
Warren
8.2 out of 10, Very good, (16)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
The price is HK$1,349
HK$1,794 total
includes taxes & fees
13 Jan - 14 Jan 2026
Bridges Resort
Fridge, microwave, oven, stovetop
Brand New Cabin On Working Farm

Brand New Cabin On Working Farm

Brand New Cabin On Working Farm
Northfield
9.6 out of 10, Exceptional, (22)
"Clean cozy quiet with nice view from the deck, unique farm setting, would stay again "
United States
Brad
The price is HK$1,166
HK$1,489 total
includes taxes & fees
7 Jan - 8 Jan 2026
Brand New Cabin On Working Farm
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (23)
"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."
United States
kevin m.
Beautiful home located in the Mad River Valley
Fridge, microwave, oven, stovetop
NEW! Studio Loft in Stowe Hollow

NEW! Studio Loft in Stowe Hollow

NEW! Studio Loft in Stowe Hollow
Stowe Hollow
10.0 out of 10, Exceptional, (179)
"Perfect location in Stowe, lovely spacious loft with great hosts!!"
United States
Max M.
The price is HK$1,155
HK$2,000 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Studio Loft in Stowe Hollow
Exterior
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub

Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub

Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
Duxbury
10.0 out of 10, Exceptional, (4)
"The house was clean and had plenty of space with good views. The road definitely has a steep incline but is easily manageable in summer and the house was close to everything we needed. "
United States
Julia A.
The price is HK$1,460
HK$4,886 total
includes taxes & fees
4 Jan - 5 Jan 2026
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
Fridge, microwave, oven, stovetop
Lovely secluded cabin on VAST trail. Drive to Stowe, Smuggs, Jay Peak & others

Lovely secluded cabin on VAST trail. Drive to Stowe, Smuggs, Jay Peak & others

Lovely secluded cabin on VAST trail. Drive to Stowe, Smuggs, Jay Peak & others
Woodbury
10.0 out of 10, Exceptional, (116)
"Amazing property, amazing place to spend a night or a week! "
United States
Amanda Danielle S.
The price is HK$1,224
HK$1,572 total
includes taxes & fees
6 Jan - 7 Jan 2026
Lovely secluded cabin on VAST trail. Drive to Stowe, Smuggs, Jay Peak & others
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex Hotel Reviews

Stowe Motel & Snowdrift

Stowe Motel & Snowdrift

10/10 Excellent
"Excellent "
Lourdes 3-night trip
Posted 1 day ago
Stowe Motel & Snowdrift

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?

The perfect adult couples retreat. 2-king bedroom right along the Mountain Road.: This holiday home rental outside of Middlesex is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Other popular places to visit in the area include Sugarbush Ski Resort and Stowe Mountain Resort.

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.