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Middlesex Vacation Rentals

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Vacation Rentals in Middlesex

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

2.0 star property
Chelsea
10.0 out of 10, Exceptional, (35)
"Lovely farm and friendly hosts"
United States
Ruilin
$140 nightly
The price is $157
Dec 1 - Dec 2
Total with taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Fridge, microwave, oven, stovetop
Brand New Cabin On Working Farm

Brand New Cabin On Working Farm

Northfield
9.6 out of 10, Exceptional, (21)
"Clean cozy quiet with nice view from the deck, unique farm setting, would stay again "
United States
Brad
$170 nightly
The price is $190
Dec 1 - Dec 2
Total with taxes and fees
Brand New Cabin On Working Farm
Property grounds
Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access

2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
$84 nightly
The price is $94
Dec 1 - Dec 2
Total with taxes and fees
Off Grid Glamping Shed with River Access
Exterior
Secluded retreat in the trees

Secluded retreat in the trees

Roxbury
10.0 out of 10, Exceptional, (36)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
$210 nightly
The price is $235
Dec 1 - Dec 2
Total with taxes and fees
Secluded retreat in the trees
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

Williamstown
10.0 out of 10, Exceptional, (53)
"It was a great central location to everything that we wanted to see and do in Vermont!"
United States
Tanner H.
$169 nightly
The price is $189
Dec 1 - Dec 2
Total with taxes and fees
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Fridge, microwave, oven, stovetop
NEW! Studio Loft in Stowe Hollow

NEW! Studio Loft in Stowe Hollow

Stowe Hollow
10.0 out of 10, Exceptional, (172)
"It was so beautiful and clean! Would definitely recommend if you are staying in Stowe and I will definitely be coming back. The loft had anything that you could possibly need and was very cozy. Great communication and very easy to find."
United States
Shyanne
$138 nightly
The price is $155
Dec 11 - Dec 12
Total with taxes and fees
NEW! Studio Loft in Stowe Hollow
Exterior
Designer A-Frame Treehouse w/hot tub on river

Designer A-Frame Treehouse w/hot tub on river

Johnson
10.0 out of 10, Exceptional, (3)
"Super well designed property. I never rate more than 9Of 10 but the prompt support from Tyler makes this stay a perfect ten. "
United States
Dipankar B.
$264 nightly
The price is $295
Dec 1 - Dec 2
Total with taxes and fees
Designer A-Frame Treehouse w/hot tub on river
Exterior
Serene Country Cabins 3 In the heart of Vermont

Serene Country Cabins 3 In the heart of Vermont

Hyde Park
10.0 out of 10, Exceptional, (80)
"Nice yard , fire pit w/wood"
United States
Todd
$226 nightly
The price is $253
Dec 1 - Dec 2
Total with taxes and fees
Serene Country Cabins 3 In the heart of Vermont
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

Woodbury
10.0 out of 10, Exceptional, (113)
"Great time, beautiful place. "
United States
Fraser D.
Lovely secluded cabin on VAST trail. Drive to Stowe, Smuggs, Jay Peak & others
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

Waterbury
9.0 out of 10, Wonderful, (30)
"The bed was super comfy!"
United States
Casey J.
$169 nightly
The price is $191
Dec 2 - Dec 3
Total with taxes and fees
Vintage farmhouse studio with on-site hot tub - near year-round recreation
Condo, 2 Bedrooms (Standard) | Private kitchen
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
$196 nightly
The price is $213
Dec 8 - Dec 9
Total with taxes and fees
Bridges Resort
Interior
The Cider Loft

The Cider Loft

Waterbury
8.0 out of 10, Very Good, (14)
"We had a great stay. The apartment was exactly as advertised and VERY clean. Beds were cozy and comfortable. It had everything we needed for a weekend stay and hosts made it easy. Well priced. Air Conditioning worked very well and despite being an attic apartment it was cool and comfortable."
Canada
Shannon G.
The Cider Loft
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Warren
9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley
Outdoor spa tub
Secluded, dog-friendly cabin with hot tub, mountain view, fireplace & deck

Secluded, dog-friendly cabin with hot tub, mountain view, fireplace & deck

Morrisville
8.6 out of 10, Excellent, (9)
"Absolutely lovely and cozy for a winter getaway "
United States
Jamie
$200 nightly
The price is $224
Dec 8 - Dec 9
Total with taxes and fees
Secluded, dog-friendly cabin with hot tub, mountain view, fireplace & deck
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Warren
10.0 out of 10, Exceptional, (22)
"Had a wonderful stay "
United States
Yang O.
Beautiful home located in the Mad River Valley
Outdoor dining
Magnificent any time of year

Magnificent any time of year

East Warren
10.0 out of 10, Exceptional, (37)
"Relaxing and comfortable! Good location to stay in Vermont. "
United States
Tony K.
$316 nightly
The price is $353
Dec 1 - Dec 2
Total with taxes and fees
Magnificent any time of year
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!

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
$228 nightly
The price is $258
Dec 4 - Dec 5
Total with taxes and fees
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
Property grounds
Serene Country Cabins 1 In the heart of Vermont

Serene Country Cabins 1 In the heart of Vermont

Hyde Park
10.0 out of 10, Exceptional, (150)
"We really enjoyed the cabin and the area. It had everything we needed for us and our dogs."
United States
Russ C.
$226 nightly
The price is $253
Dec 1 - Dec 2
Total with taxes and fees
Serene Country Cabins 1 In the heart of Vermont
Fireplace, books
Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook

Warren
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
$389 nightly
The price is $436
Dec 1 - Dec 2
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
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

Duxbury
10.0 out of 10, Exceptional, (3)
"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.
$433 nightly
The price is $485
Dec 4 - Dec 5
Total with taxes and fees
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
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

Field Guide Lodge

Field Guide Lodge

10/10 Excellent
"This was such a cute lodge in the perfect location!"
Derrick 2-night trip
Posted 3 days ago
Field Guide Lodge

Find out more about Middlesex

Everything you need to know about Middlesex vacation rentals

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

Middlesex vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlesex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

New! Vermont modern farmhouse in Stowe Village: Visitors like this Middlesex vacation home rental. It is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.