Middlebury Holiday Rentals from NZ$249: Search Short-Term Rentals

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

Water front home with large two tiered deck! 2 bathrooms 😂 : This holiday home rental outside of Middlebury is located on a lake, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Our top choices for Middlebury holiday rentals

A two-story house with a porch, two red doors, and a blue exterior.

1. Downtown Middlebury 3 BR Home - Walk Everywhere!

Middlebury

Karyn M.

includes taxes & fees

28 Sept - 29 Sept

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

2. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

includes taxes & fees

26 Oct - 27 Oct

A historic town with a river, buildings with traditional architecture, and a waterfall.

3. Downtown Middlebury Waterfall Studio Apartment

Middlebury

Steve S.

includes taxes & fees

5 Oct - 6 Oct

A wooden cabin with a snow-covered roof, surrounded by trees and snow.

4. Robert Frost Mountain Cabins

Ripton

Joe

includes taxes & fees

1 Oct - 2 Oct

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

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

Leicester

Laura Ann

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a living room with a sofa.

6. Gracious two bedroom just minutes to Middlebury!

New Haven

includes taxes & fees

28 Sept - 29 Sept

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

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

Ripton

Susan

includes taxes & fees

29 Sept - 30 Sept

A living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has white walls and a blue carpet.

8. Tasteful two bedroom just minutes to Middlebury!

New Haven

includes taxes & fees

28 Sept - 29 Sept

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

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

Ripton

Linda

includes taxes & fees

8 Oct - 9 Oct

A wooden interior with large windows, a dining table, chairs, and a sofa.

10. 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.

includes taxes & fees

28 Sept - 29 Sept

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

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

Ripton

Steven

includes taxes & fees

15 Oct - 16 Oct

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.

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a fireplace, a sofa, a coffee table, and a white door.

13. Beautiful Lake House with whole house renovation & fresh modern appeal!

Crown Point

Phillip K.

includes taxes & fees

30 Sept - 1 Oct

A wooden deck with blue chairs and a barbecue grill.

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

Ripton

Alex

includes taxes & fees

29 Sept - 30 Sept

A bedroom with a bed, bedside table, lamp, and a ceiling fan.

15. Little City Big Heart

Vergennes

Patsy H.

includes taxes & fees

6 Oct - 7 Oct

A wooden cabin with a snow-covered roof and a lit entrance.

16. Adorable cabin with screened porch and private fire pit

Ripton

Sorin

includes taxes & fees

25 Oct - 26 Oct

17. Immaculate mountain cabin with awe inspiring sunrise and mountain views

Ripton

Sara S.

includes taxes & fees

8 Oct - 9 Oct

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

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

Ripton

Kelly I.

includes taxes & fees

25 Oct - 26 Oct

A wooden staircase leading to a dock by a lake surrounded by trees.

19. Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Leicester

Eric A.

includes taxes & fees

28 Sept - 29 Sept

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Top Middlebury Hotel Reviews

Brandon Inn

8/10 Good

"So much character to the inn, definitely loved it and would return. The location is phenomenal too, very cute town. I gave it a 4 versus a 5 because when we arrived no one at the desk to check us in but there was a sign to go into the dining room for check in. Whelp, not a soul to be found. We walked around the downstairs area for a good 15min asking people if they worked there 🙄. Finally got a yes and the young woman was not immediately attentive nor apologetic. I would definitely stay there again and not let that one issue deter me."

Circle Court Motel

8/10 Good

"Huge thank you; the staff was so helpful with information and guidance on where to eat and how to navigate the town. Just a few items worth mentioning: it's a basic room, no fancy fixtures. The lamp between the two queen-size beds didn't work, which wasn't a problem because of the overhead light. Some items need updating. But overall, our goal was just a place to sleep, and it was comfortable; the sheets were soft, and we had a good night's sleep- nice and quiet! Would recommend and would definitely stay there again."

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

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

Middlebury holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as NZ$249 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday 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 holiday.

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.

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Vermont Folklife Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middlebury has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: This holiday home rental outside of Middlebury is located on a lake, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middlebury?

Expedia has 16 holiday 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 Vermont Folklife Center and UVM Morgan Horse Farm.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Middlebury holiday rentals

1. Downtown Middlebury 3 BR Home - Walk Everywhere!

2. Purple Door Cottage in the heart of Middlebury!