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

Middlesex Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middlesex vacation rentals

A picnic area with a wooden bench, green chairs, and a fire pit.

1. Cozy 1-bedroom loft apartment in lovely Duxbury

Cozy 1-bedroom loft apartment in lovely Duxbury
Duxbury
9.8 out of 10, Exceptional, (27 reviews)
"Cozy loft space with kitchen, bath and plenty of room."
United States
Beatriz
$160 nightly
The price is $179
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom loft apartment in lovely Duxbury
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, (39 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
$155 nightly
The price is $173
Nov 12 - Nov 13
Total with taxes and fees
Brand New Cabin On Working Farm
A wooden cabin with a glass door and windows, a stone patio with lounge chairs, and a view of a sunset.

3. Countryside Cottage with Sauna and Fireplace

Countryside Cottage with Sauna and Fireplace
Berlin
10.0 out of 10, Exceptional, (6 reviews)
"Nice clean cottage with everything you could need. Easy check in and great communication"
United States
Justin F.
$227 nightly
The price is $256
Nov 12 - Nov 13
Total with taxes and fees
Countryside Cottage with Sauna and Fireplace
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.
$260 nightly
The price is $293
Nov 12 - Nov 13
Total with taxes and fees
Vintage farmhouse studio with on-site hot tub and mountain views
A two-story red building with a black front door, white trim, and a Christmas wreath.

5. The Cider Loft

The Cider Loft
Waterbury
8.4 out of 10, Very good, (33 reviews)
"It was centrally located for the time we were visiting the area."
United States
Rose
$204 nightly
The price is $231
Nov 12 - Nov 13
Total with taxes and fees
The Cider Loft
A cozy living room with a dark green sofa and a dining area with wooden chairs and a white table.

6. Stowe Cabins in the Woods

Stowe Cabins in the Woods
2.5 star property
Waterbury Center
8.8 out of 10, Excellent, (315 reviews)
"Love the layout of the cabin, felt comfortable and cozy."
United States
Jesus
$230 nightly
The price is $253
Nov 12 - Nov 13
Total with taxes and fees
Stowe Cabins in the Woods
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

7. 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
9.8 out of 10, Exceptional, (13 reviews)
"This home was just what we needed to rest our heads while on a long road trip with the family."
United States
Martin H.
$475 nightly
The price is $532
Nov 19 - Nov 20
Total with taxes and fees
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
A red barn with two white garage doors, a triangular roof, and a wreath on the front wall.

8. NEW! Studio Loft in Stowe Hollow

NEW! Studio Loft in Stowe Hollow
Stowe Hollow
10.0 out of 10, Exceptional, (218 reviews)
"Great stay"
United States
Daniel
$163 nightly
The price is $184
Nov 17 - Nov 18
Total with taxes and fees
NEW! Studio Loft in Stowe Hollow
A modern kitchen with a marble island, stainless steel appliances, and wooden stools.

9. 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, (60 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
$431 nightly
The price is $487
Nov 12 - Nov 13
Total with taxes and fees
Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain
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, (13 reviews)
"This was a comfortable location for our travels through New England."
United States
Bryan
$215 nightly
The price is $243
Nov 12 - Nov 13
Total with taxes and fees
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.
$326 nightly
The price is $369
Nov 16 - Nov 17
Total with taxes and fees
Go Skiing or Hiking from an Enchanting, Light-Filled Home
A stack of firewood on a metal rack outside a building.

12. 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, (62 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.
$182 nightly
The price is $204
Nov 12 - Nov 13
Total with taxes and fees
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
A spacious kitchen with wooden cabinets, a large island, and a hanging light fixture.

13. Beautiful Home with views and a hot tub 10 minutes from Sugarbush Resort

Beautiful Home with views and a hot tub 10 minutes from Sugarbush Resort
Moretown
10.0 out of 10, Exceptional, (16 reviews)
"Very nice property with lots of amenities, convenient location, and excellent communication with host. "
United States
CAROLYN M.
$450 nightly
The price is $504
Dec 1 - Dec 2
Total with taxes and fees
Beautiful Home with views and a hot tub 10 minutes from Sugarbush Resort
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.

14. 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
$231 nightly
The price is $233
Nov 12 - Nov 13
Total with taxes and fees
Luxury Living Space|Gorgeous Mountain Views
A room with a sloped ceiling, large windows, two armchairs, a small round table with a plant, and a white door.

15. Renovated Condo in Luxury Neighborhood

Renovated Condo in Luxury Neighborhood
Stowe
9.6 out of 10, Exceptional, (35 reviews)
"Clean, easy check in and good communication "
United States
Patti C.
$237 nightly
The price is $239
Nov 12 - Nov 13
Total with taxes and fees
Renovated Condo in Luxury Neighborhood
A living room with a sofa, a coffee table, a TV, and a ceiling fan.

16. Near Ski Slopes! Quaint Richmond Apt w/ Mtn Views

Near Ski Slopes! Quaint Richmond Apt w/ Mtn Views
3.0 star property
Richmond
$204 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
Near Ski Slopes! Quaint Richmond Apt w/ Mtn Views
A spacious living room with a large gray sectional sofa, a wooden coffee table, and a dining area with a table and chairs.

17. Updated Rustic Vermont Style Condo in Heart of Stowe

Updated Rustic Vermont Style Condo in Heart of Stowe
Stowe
8.6 out of 10, Excellent, (41 reviews)
"Great place!"
United States
Lori
$254 nightly
The price is $257
Nov 12 - Nov 13
Total with taxes and fees
Updated Rustic Vermont Style Condo in Heart of Stowe
A spacious loft with a high ceiling, skylights, a living area with sofas, a dining table, and a staircase leading to an upper level.

18. 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, (40 reviews)
"The home was comfortable and convenient. The location was excellent."
United States
Amanda J.
$454 nightly
The price is $513
Nov 12 - Nov 13
Total with taxes and fees
Updated vintage farmhouse unit with on-site hot tub near Stowe
A two-story house with a red door, a covered porch, and a well-maintained lawn.

19. 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, (84 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
$317 nightly
The price is $358
Nov 12 - Nov 13
Total with taxes and fees
Stowe retreat with king bed and futon near Stowe Mountain Resort
A modern kitchen with a dining area, featuring a wooden table set for four, a stove, and a sink.

20. Charming 2BR abode: Newly Restored, Full of Light, 2 Min to Stowe Center!"

Charming 2BR abode: Newly Restored, Full of Light, 2 Min to Stowe Center!"
Lower Village
9.2 out of 10, Wonderful, (14 reviews)
"Clean, easy to access and was as described. About a 15 minute drive to Stowe. We enjoyed and would stay again if we return. "
United States
Stephanie A.
$282 nightly
The price is $319
Nov 17 - Nov 18
Total with taxes and fees
Charming 2BR abode: Newly Restored, Full of Light, 2 Min to Stowe Center!"
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

Smugglers' Notch Resort

Smugglers' Notch Resort

10/10 Excellent
"I wish there was coffee and creamer available in the house."
Manisha 1-night trip
Posted 16 hours ago
Smugglers' Notch Resort

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 $166 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?

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.

How many vacation rentals are there in Middlesex?

Expedia has 3 vacation 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 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.