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

Middlesex Vacation Rentals

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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 cozy cabin interior with wooden walls, a sofa, a rocking chair, a table, and a window with a view of greenery.

1. Brand New Cabin On Working Farm

Brand New Cabin On Working Farm
Northfield
9.8 out of 10, Exceptional, (33 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 two-story red building with a black front door, white trim, and a Christmas wreath.

2. 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.
$239 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
The Cider Loft
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 spacious loft with a high ceiling, skylights, a living area with sofas, a dining table, and a staircase leading to an upper level.

4. 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.

5. 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 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.
$304 nightly
The price is $341
Sep 28 - Sep 29
Total with taxes and fees
Go Skiing or Hiking from an Enchanting, Light-Filled Home
An outdoor patio area with wooden tables and benches, a barbecue grill, and a wooden shelter.

7. Lovely cabin nestled in the woods one minute from Sugarbush Resort

Lovely cabin nestled in the woods one minute from Sugarbush Resort
Warren
9.8 out of 10, Exceptional, (29 reviews)
"Hot tub was enjoyable and location was great"
United States
Linnea P.
Lovely cabin nestled in the woods one minute from Sugarbush Resort
A room with a sloped ceiling, large windows, two armchairs, a small round table with a plant, and a white door.

8. 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.
$249 nightly
The price is $252
Sep 28 - Sep 29
Total with taxes and fees
Renovated Condo in Luxury Neighborhood
A room with a checkered bedspread, a patterned rug, and two black cylindrical objects.

9. 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 28 - Sep 29
Total with taxes and fees
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!

10. 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)
"Place was great, exactly what we needed."
United States
Andrew D.
Beautiful brand new cabin one minute from Sugarbush Resort
A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

11. Ski-in/ski-out condo with mountain view, seasonal pool

Ski-in/ski-out condo with mountain view, seasonal pool
Warren
$262 nightly
The price is $293
Oct 27 - Oct 28
Total with taxes and fees
Ski-in/ski-out condo with mountain view, seasonal pool
A spacious room with a large window, a beige sofa, a wooden dining table, and a small coffee table.

12. Four Season Condo: ski, hike, golf, mountain bike & seasonal pool

Four Season Condo: ski, hike, golf, mountain bike & seasonal pool
Warren
$195 nightly
The price is $219
Sep 30 - Oct 1
Total with taxes and fees
Four Season Condo: ski, hike, golf, mountain bike & seasonal pool
A rustic cabin surrounded by autumn foliage.

13. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
A wooden deck with a view of a forested mountain range.

14. Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes

Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes
Warren
9.4 out of 10, Exceptional, (38 reviews)
"Nice view - Well-stocked kitchen - Nice pool and tennis courts "
United States
Michael L.
$297 nightly
The price is $333
Oct 27 - Oct 28
Total with taxes and fees
Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes
A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

15. Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
East Warren
9.6 out of 10, Exceptional, (17 reviews)
"Great location, plenty of space, everything in house worked as described. Thank you!!"
United States
Daniel B.
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
A cozy cabin interior with a wooden floor, a bed with white bedding, wicker chairs with patterned cushions, a small round table, and a ceiling fan.

16. Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (40 reviews)
"Host was very friendly and accommodating "
United States
Alexandria
$201 nightly
The price is $225
Oct 8 - Oct 9
Total with taxes and fees
Cozy Cabin Retreat
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

17. 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
9.4 out of 10, Exceptional, (23 reviews)
"Enjoyable stay"
United States
Eric W.
$222 nightly
The price is $249
Oct 19 - Oct 20
Total with taxes and fees
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
A bedroom with a bed, a white sofa, a wooden ceiling, and a painting on the wall.

18. 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, (35 reviews)
"Great spot, would stay again!"
United States
Kelly K.
$240 nightly
The price is $272
Oct 25 - Oct 26
Total with taxes and fees
Vintage farmhouse studio with on-site hot tub - near year-round recreation
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.

19. 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.
$334 nightly
The price is $337
Sep 30 - Oct 1
Total with taxes and fees
Luxury Living Space|Gorgeous Mountain Views
A house with a porch, outdoor seating, and a garden.

20. Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT

Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT
Montpelier
9.6 out of 10, Exceptional, (32 reviews)
"We had a great time in Vermont and happy we chose to stay here! Great location in downtown to walk to a grocery store or Main Street. We felt welcome and loved the beautiful hilltop view!"
United States
Anonymous traveler
$347 nightly
The price is $392
Oct 8 - Oct 9
Total with taxes and fees
Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT
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

Topnotch Resort

Topnotch Resort

10/10 Excellent
"The hotel had beautiful grounds with 2 outdoor heated pools which were open in September. The staff were very helpful. We rented bikes from across a the road and cycled along the path to the town. The breakfast was expensive."
Denise 2-night trip
Posted less than an hour ago
Topnotch 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 $175 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.