Middlebury Holiday Rentals from NZ$342: 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 large grassy field with a historic building in the background.

1. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

includes taxes & fees

16 Nov - 17 Nov

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

includes taxes & fees

15 Nov - 16 Nov

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

3. Tasteful two bedroom just minutes to Middlebury!

New Haven

includes taxes & fees

16 Nov - 17 Nov

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

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

Ripton

Alex

includes taxes & fees

14 Nov - 15 Nov

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

5. Gracious two bedroom just minutes to Middlebury!

New Haven

includes taxes & fees

16 Nov - 17 Nov

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

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

Leicester

Laura Ann

includes taxes & fees

15 Nov - 16 Nov

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

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

Salisbury

Christopher T.

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

19 Nov - 20 Nov

A red barn in a forested area with mountains in the background.

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

Ripton

Lani C.

includes taxes & fees

28 Nov - 29 Nov

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

10. Cozy and pristine timberframe cabin

Ripton

Karen H.

includes taxes & fees

15 Nov - 16 Nov

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

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

Ripton

Susan

includes taxes & fees

15 Nov - 16 Nov

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

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

Ripton

Steven

includes taxes & fees

18 Nov - 19 Nov

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

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

Warren

Eric W.

includes taxes & fees

16 Nov - 17 Nov

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

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

Warren

includes taxes & fees

14 Nov - 15 Nov

A rustic cabin surrounded by autumn foliage.

15. Beautiful home located in the Mad River Valley

Warren

Sloan S.

includes taxes & fees

18 Nov - 19 Nov

16. Beautiful home located in the Mad River Valley

Warren

Allie T.

includes taxes & fees

18 Nov - 19 Nov

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

17. Beautiful home located in the Mad River Valley

Warren

Lyra F.

includes taxes & fees

2 Dec - 3 Dec

An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and trees.

18. Light-filled Bridges condo overlooking the mountains, by the free shuttle

Warren

Scott H.

includes taxes & fees

14 Nov - 15 Nov

An outdoor seating area with Adirondack chairs, a stone fire pit, and a picnic table.

19. The Bridges condo with balcony, two saunas and free coffee and tea

Warren

"Very cozy and perfect! We enjoyed the stay for the night. We weren’t able to use the facilities but the accommodation was very comfortable, seating and bed. I could hear a stream below in the woods and was nice from the porch. There is an apartment above, so you can hear walking but in was totally fine. The pool, grills and tennis right across the parking. It was very wooded and up in the mountains so the fans and windows were perfect. We would definitely go back!"

katherine l.

includes taxes & fees

14 Nov - 15 Nov

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

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

Warren

Michael L.

includes taxes & fees

16 Nov - 17 Nov

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Find holiday rentals that suit your style

Top Middlebury Hotel Reviews

A row of Adirondack chairs in a lush green field with a backdrop of mist-covered hills and a purple sky.

Mad River Inn

Waitsfield

10/10 Excellent

This is an amazing Inn (Bed and Breakfast) that we stayed at. The two owners, Brandon and Susannah, are amazing and generous hosts, with homemade cookies (yum!), breakfast and many other amenities on site. They also gave excellent recommendations, not just for the local area but also for the rest of our holiday in the USA. My partner and I absolutely recommend this place for anyone looking for a home away from home.

Brett

A white building with green shutters and a sign that reads "Storeham Inn."

Shoreham Inn

Shoreham

10/10 Excellent

Anonymous traveller

A library with leather sofas, bookshelves, and wall-mounted lamps.

Bristol Suites

Bristol

10/10 Excellent

Beautiful boutique hotel with similarities to a B&B. Room we stayed in (South Mountain Suite) was tastefully decorated and very spacious with comfortable bed and all the features you would want for. Easy and convenient parking at the rear of property. The town of Bristol is a beautiful small village with very good quality dining options. The Bobcat cafe is the best rated place in town and does not disappoint, truly fantastic quality.

Steven

A stone fireplace with a sign reading "Lodge" above it, a bear statue, and a wooden table with snacks and drinks.

White Horse Lodge

Waitsfield

10/10 Excellent

Anonymous traveller

A forested area with a river, rocks, and three wooden Adirondack chairs.

The Warren Lodge

Warren

8/10 Good

Good clean room and comfy bed. Communal area with a dining table, microwave and tea/coffe. Firepits and chairs by the river and easy access to the river. But - make sure you get the wifi password out of the guest guidebook before leaving civilisation. The book wouldn't download to our phone and the cell service is patchy so we initially had no internet and had missed the email communications from the manager. This was the first time we had experienced a self check in place. The manager was...

Justine

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$342 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 UVM Morgan Horse Farm and Vermont Folklife Center.

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.

Middlebury Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlebury holiday rentals

1. Purple Door Cottage in the heart of Middlebury!

2. Charming one bedroom just minutes to Middlebury!

3. Tasteful two bedroom just minutes to Middlebury!

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

5. Gracious two bedroom just minutes to Middlebury!

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

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

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. Cozy and pristine timberframe cabin

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

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

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

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

15. Beautiful home located in the Mad River Valley

16. Beautiful home located in the Mad River Valley

17. Beautiful home located in the Mad River Valley

18. Light-filled Bridges condo overlooking the mountains, by the free shuttle

19. The Bridges condo with balcony, two saunas and free coffee and tea

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

Find holiday rentals that suit your style

Top Middlebury Hotel Reviews

Mad River Inn

10/10 Excellent

Find out more about Middlebury

Middlebury holiday rentals: An excellent choice for every season

How to find incredible deals on Middlebury rentals

Frequently Asked Questions

Are there holiday rentals in Middlebury?

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

How many holiday rentals are there in Middlebury?

What’s there to see and do in Middlebury?

What’s a holiday rental in Middlebury like?