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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (25 reviews)
"Place was super cute and they let me bring my dog!"
United States
Sharyn and Kiersten v.
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, (32 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
$163 nightly
The price is $182
Oct 20 - Oct 21
Total with taxes and fees
Brand New Cabin On Working Farm
A modern kitchen with a marble island, stainless steel appliances, and wooden stools.

3. 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
$427 nightly
The price is $483
Sep 28 - Sep 29
Total with taxes and fees
Loaded Kitchen • Sleeps 6, Seats 10 • Walk to Dining • 15 Min to Stowe Mountain
A house with a porch, outdoor seating, and a garden.

4. 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.
Artful Lodging 1st Fl'r 2 Bedroom Apt in Civil War Infirmary Home Montpelier VT
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, (26 reviews)
"The location was very close to Stowe Mountain, which made our stay very convenient to us. "
United States
Shain G.
$202 nightly
The price is $228
Oct 27 - Oct 28
Total with taxes and fees
The Cider Loft
A neatly made bed with striped bedding, a beige throw blanket, and patterned pillows. There are two bedside lamps on wooden nightstands.

6. 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.
$306 nightly
The price is $343
Sep 28 - Sep 29
Total with taxes and fees
Go Skiing or Hiking from an Enchanting, Light-Filled Home
A modern kitchen with a central island, built-in appliances, and pendant lighting.

7. 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
Bridges Resort
A wooden cabin with a snow-covered deck and a lit interior, surrounded by trees.

8. Cozy warm treehouse with Amazing views! Winter Paradise! Hike from cabin

Cozy warm treehouse with Amazing views! Winter Paradise! Hike from cabin
Moretown
10.0 out of 10, Exceptional, (2 reviews)
"The treehouse is very unique and full of character. It's out of the way but in a phenomenal location for quiet and privacy, with views of the mountains that are breathtaking. I very much enjoyed my stay and the ability it allowed me to experience the countryside of Vermont."
United States
Austin M.
Cozy warm treehouse with Amazing views! Winter Paradise! Hike from cabin
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

9. 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, (12 reviews)
"This was a great house for my family with adult children. It was easy to get to the places we had planned to visit."
United States
Dianne
$436 nightly
The price is $488
Oct 1 - Oct 2
Total with taxes and fees
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
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
8.8 out of 10, Excellent, (9 reviews)
"Place is great quiet comfy clean and so well equipped if available would definitely stay again"
United States
Brian
$265 nightly
The price is $299
Sep 27 - Sep 28
Total with taxes and fees
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
A spacious loft with a high ceiling, skylights, a living area with sofas, a dining table, and a staircase leading to an upper level.

11. All-season escape in a vintage farmhouse with updated interior & on-site hot tub

All-season escape in a vintage farmhouse with updated interior & on-site hot tub
Waterbury
9.0 out of 10, Wonderful, (38 reviews)
"The home was comfortable and convenient. The location was excellent."
United States
Amanda J.
$429 nightly
The price is $484
Oct 27 - Oct 28
Total with taxes and fees
All-season escape in a vintage farmhouse with updated interior & on-site hot tub
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, (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
$177 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
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.

13. 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, (50 reviews)
"Perfect spot for visiting Stowe and Vermont- host was very responsive."
United States
Emma S.
$393 nightly
The price is $444
Sep 30 - Oct 1
Total with taxes and fees
Stowe Lofts- 2-bedroom condo, peaceful, 5 min to Stowe, Ask about pet policy
A spacious living room with a wooden floor, a gray sofa, a coffee table, and a dining area with wooden chairs and a table.

14. 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.
$674 nightly
The price is $761
Oct 5 - Oct 6
Total with taxes and fees
Beautiful Family Home Central to Mad River Valley
A house surrounded by dense trees with sunlight filtering through the leaves.

15. Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (46 reviews)
"Very cozy and easy check in!"
United States
Emily R.
$233 nightly
The price is $261
Oct 13 - Oct 14
Total with taxes and fees
Secluded retreat in the trees
A water park with multiple slides and a swimming pool area.

16. Smugglers' Notch Resort

Smugglers' Notch Resort
3.0 star property
Jeffersonville
7.8 out of 10, Good, (141 reviews)
"Spacious and accomodated my family well."
United States
Patrick
$301 nightly
The price is $326
Oct 26 - Oct 27
Total with taxes and fees
Smugglers' Notch 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.

17. 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.
$255 nightly
The price is $258
Sep 27 - Sep 28
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.

18. 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.
$258 nightly
The price is $261
Sep 28 - Sep 29
Total with taxes and fees
Renovated Condo in Luxury Neighborhood
A two-story house with a balcony, surrounded by a well-maintained lawn and trees.

19. 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, (29 reviews)
"Fabulous location for a home base for a trip to Stowe!"
United States
Lindsey C.
$265 nightly
The price is $268
Sep 27 - Sep 28
Total with taxes and fees
Modern Condo Surrounded by Nature I Heart of Stowe

20. Cozy 2bdrm w/ Pond View - Best Location!

Cozy 2bdrm w/ Pond View - Best Location!
Stowe
9.4 out of 10, Exceptional, (13 reviews)
"a very cute place to stay! good location — close to town and a close enough drive to Stowe mountain. "
United States
paige m.
$367 nightly
The price is $395
Oct 25 - Oct 26
Total with taxes and fees
Cozy 2bdrm w/ Pond View - Best Location!
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

Bluebird Cady Hill Lodge

Bluebird Cady Hill Lodge

10/10 Excellent
"Beautiful and clean property. Great location."
Shelly 1-night trip
Posted 3 hours ago
Bluebird Cady Hill 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 $201 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. Stowe Mountain Resort and Ben and Jerry's Factory 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.