Middlebury Vacation Rentals from $55: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Middlebury has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂 : Visitors like this Middlebury vacation home rental. It is located on a lake and has a patio, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Our top choices for Middlebury vacation rentals

A large grassy field with a historic building in the background.

1. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

$336 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, a coffee machine, and a wooden accent wall.

2. Charming one bedroom just minutes to Middlebury!

New Haven

Jane

$201 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with stainless steel appliances, a granite countertop, and pendant lighting.

3. Gracious two bedroom just minutes to Middlebury!

New Haven

$285 nightly

Nov 10 - Nov 11

Total with taxes and fees

A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

4. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester

Laura Ann

$171 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

5. Tasteful two bedroom just minutes to Middlebury!

New Haven

$282 nightly

Nov 11 - Nov 12

Total with taxes and fees

A lakeside view with a fire pit and chairs, surrounded by mountains and trees.

6. Doc's Lake house 1st floor, 2 bedroom apartment

Salisbury

Christopher T.

$217 nightly

Nov 10 - Nov 11

Total with taxes and fees

A snow-covered house with a lit entrance and a small outdoor light feature.

7. Glamping hut with WiFi in Ripton, biking, hiking, skiing

Ripton

Alex

$186 nightly

Nov 10 - Nov 11

Total with taxes and fees

A log cabin with a gravel driveway leading to it, surrounded by dense forest.

8. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Ripton

Linda

$299 nightly

Nov 10 - Nov 11

Total with taxes and fees

A hammock tied between trees with a view of a grassy field and mountains in the background.

9. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

Ripton

Lani C.

$240 nightly

Nov 28 - Nov 29

Total with taxes and fees

A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

10. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Ripton

Susan

$299 nightly

Nov 10 - Nov 11

Total with taxes and fees

A wooden table with a bottle of wine, glasses, and grapes.

11. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Ripton

Steven

$299 nightly

Nov 10 - Nov 11

Total with taxes and fees

A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

12. Cozy and pristine timberframe cabin

Ripton

Karen H.

$299 nightly

Nov 15 - Nov 16

Total with taxes and fees

A spacious dining area with a long table set for six, large windows offering a view of the outdoors, and a wooden ceiling structure.

13. Beautiful timber frame just minutes to Middlebury!

New Haven

"We were 8 people coming to VT to watch our girls play lacrosse at Middlebury. The house is as pictured and perfect for large groups. We really had a great time, it was spacious and perfect for hanging out with a large group. We wished the weather was better so we could use the fire pit. The owner of the property was very easy to deal with and very accommodating. We would all definitely stay here again and recommend a stay at this house. Some of us even said it would be perfect for a small...

Suzanne L.

$726 nightly

Nov 10 - Nov 11

Total with taxes and fees

A covered porch with outdoor furniture, a ceiling fan, and a wooden deck.

14. Little City Big Heart

Vergennes

Craig S.

$414 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

15. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

Warren

$272 nightly

Nov 10 - Nov 11

Total with taxes and fees

A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

16. Inviting timber frame cabin in Vermont's Green Mountains

Ripton

Kelly I.

$299 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with a large window overlooking a forest in autumn.

17. Beautiful home located in the Mad River Valley

Warren

Lyra F.

$243 nightly

Dec 2 - Dec 3

Total with taxes and fees

A wooden deck with a view of a forested mountain range.

18. The Bridges condo with forested views, three pools and two saunas

Warren

Michael L.

$304 nightly

Nov 13 - Nov 14

Total with taxes and fees

A building with a wooden deck leading to a door marked 'Paradise.'

19. Condo with secure ski locker, study and central A/C, a half mile from Sugarbush

Warren

Anonymous traveler

$377 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

20. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

Warren

Eric W.

$224 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Top Middlebury Hotel Reviews

Lake Bomoseen Lodge

10/10 Excellent

"This property is fantastic. Definitely will stay again if I'm in the area. Check out the tap room. The food was delicious."

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10/10 Excellent

"A very pleasant surprise. From a very simple check in to a cabin with all the amenities and then some it was a great few days. Jeff was a great host. His communication was fast and very helpful. We look forward to a return visit!!!!!!!!!!Jim & Paula"

Emrose Luxury Cabins

8/10 Good

"The cabins are new and well maintained. There are pots and pans and spatulas but incredibly no coffee maker. I don’t believe I’ve ever stayed in a room at any price point without a coffee maker. Also, the bed is up against a wall so you have to choose who has to crawl in and out of the bed to go to the bathroom, get a glass of water, etc. Not fun. There was also no contact information for management, so when we couldn’t figure out how to get the heater or fireplace working, we had to chat with Hotels.com who claimed our room did not have heat. Really? Vermont in the fall? Are you kidding me? After I almost lost my mind, they had someone from hotel management call me and instruct me how to turn the heat on. He was very nice and solved the problem, but how about providing contact information of someone on premises if there is an issue? The place is fairly new, and I like the concept, but they have a few things to iron out before they are ready for prime time. Let’s start with an $25 coffee maker in every room. Is that too much to ask? And Hotels.com really needs to get their chat proficiency together…."

Find out more about Middlebury

Everything you need to know about Middlebury 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 Middlebury 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 Middlebury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. 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 Middlebury 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 $55 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 Middlebury rentals

At Expedia, we put the best Middlebury 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 Middlebury 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 Middlebury 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 Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Middlebury?

Yes, we offer vacation rentals in Middlebury close to Vermont Folklife Center, or you can select a more remote option if you want a relaxing stay. Our travelers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.

What are some of the best vacation home rentals that Middlebury has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: Visitors like this Middlebury vacation home rental. It is located on a lake and has a patio, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middlebury?

Expedia has 16 vacation rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include Town Hall Theater and Henry Sheldon Museum of Vermont History, whereas Green Mountain National Forest and Cornwall Swamp Wildlife Management Area are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include UVM Morgan Horse Farm and Vermont Folklife Center.

What’s a vacation rental in Middlebury like?

Vacation rentals are private properties you can stay in for a couple of days or more in Middlebury. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.

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Check prices for these dates

Our top choices for Middlebury vacation rentals

1. Purple Door Cottage in the heart of Middlebury!

2. Charming one bedroom just minutes to Middlebury!

3. Gracious two bedroom just minutes to Middlebury!

4. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

5. Tasteful two bedroom just minutes to Middlebury!

6. Doc's Lake house 1st floor, 2 bedroom apartment

7. Glamping hut with WiFi in Ripton, biking, hiking, skiing

8. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

9. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

10. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

11. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

12. Cozy and pristine timberframe cabin

13. Beautiful timber frame just minutes to Middlebury!

14. Little City Big Heart

15. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

16. Inviting timber frame cabin in Vermont's Green Mountains

17. Beautiful home located in the Mad River Valley

18. The Bridges condo with forested views, three pools and two saunas

19. Condo with secure ski locker, study and central A/C, a half mile from Sugarbush

20. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

Find vacation rentals that suit your style

Top Middlebury Hotel Reviews

Lake Bomoseen Lodge

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Middlebury Sweets Motel

The Warren Lodge

Emrose Luxury Cabins

Cozy Loft for two with Hot Tub & Mtn Views

Swift House Inn

Find out more about Middlebury

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