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Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2.0 star property
10.0 out of 10, Exceptional, (31)
"Would definitely come back!"
The price is NZ$250
includes taxes & fees
2 Oct - 3 Oct
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

9.8 out of 10, Exceptional, (22)
"House was very clean. Great view of lake. "
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

The Wellington Cottage

3.0 star property
10.0 out of 10, Exceptional, (3)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
The Wellington Cottage

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10.0 out of 10, Exceptional, (5)
"We enjoyed and appreciated our stay at The Cozy Cottage. Griffon was very nice and allowed us an early check in and welcomed us to stay as long as we wanted on the day of check out. Would definitely recommend and stay again! "
Charming 3-bedroom house located on Main Street in Downtown Middlebury

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (60)
"The house and yard are beautiful. Very modern with all the amenities. Easy to find, great location and very serene. The hot tub was great and very relaxing. I enjoyed the use of the washer and dryer and all the different spots to each do our own thing when we wanted. Definitely recommend!! "
The price is NZ$489
includes taxes & fees
5 Oct - 6 Oct
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

10.0 out of 10, Exceptional, (24)
"House was nice & clean, enjoyed our stay!"
The price is NZ$554
includes taxes & fees
30 Sept - 1 Oct
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

The Loft 3BR Apartment with Scenic Deck

6.0 out of 10, (1)
"Okay, we came after it had snow a few days prior and nothing was cleared on the many steps nor ramp path, so 6 of us trudged thru snow then tracked snow up wooden stairs that really need some type of padding. NOT for elderly or anyone with steps problems.The 3 beds were so uncomfortable, squeaky and thin; I was able to can feel the mattress quilting through the sheets.The decorative pillow in my bedroom, smelled happily of someone’s cologne.Not impressed at all. Not terrible, but no screens in...
The price is NZ$816
includes taxes & fees
5 Oct - 6 Oct
The Loft 3BR Apartment with Scenic Deck

Live & Love Life on the Lake at Sunset Cottage!

9.6 out of 10, Exceptional, (54)
"Very relaxing, nice property. "
The price is NZ$451
includes taxes & fees
8 Oct - 9 Oct
Live & Love Life on the Lake at Sunset Cottage!

Little Luxe Retreat - Tiny Home #7

10.0 out of 10, Exceptional, (1)
"Very enjoyable stay."
The price is NZ$401
includes taxes & fees
6 Oct - 7 Oct
Little Luxe Retreat - Tiny Home #7

Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

10.0 out of 10, Exceptional, (8)
"Place is beautiful "
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Carefree Lakefront Cottage/ 11 mins to skiing

10.0 out of 10, Exceptional, (206)
"Such a great little place! I could live there!!!!! Would stay again!!"
Carefree Lakefront Cottage/ 11 mins to skiing

Emma's Place

10.0 out of 10, Exceptional, (54)
"Enjoyed our stay! Would definitely stay here again."
The price is NZ$558
includes taxes & fees
1 Oct - 2 Oct
Emma's Place

Beautiful Waterfront Home on Baugo Bay

9.6 out of 10, Exceptional, (34)
"Great stay and great host!"
The price is NZ$1,138
includes taxes & fees
1 Oct - 2 Oct
Beautiful Waterfront Home on Baugo Bay

Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

2.0 star property
10.0 out of 10, Exceptional, (8)
Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

10.0 out of 10, Exceptional, (118)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

9.2 out of 10, Wonderful, (21)
"House was big enough for the entire family and the amenities were excellent for the kids activities. "
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

Book your Fall Getaway soon! Our Season ends November 22! We offer Breakfast !

10.0 out of 10, Exceptional, (4)
"Absolutely wonderful property and hosts…. Will definitely stay again. "
Book your Fall Getaway soon! Our Season ends November 22! We offer Breakfast !

Lake Retreat With Hot Tub

10.0 out of 10, Exceptional, (23)
"This was perfect for our short getaway!"
The price is NZ$356
includes taxes & fees
30 Oct - 31 Oct
Lake Retreat With Hot Tub

Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

9.6 out of 10, Exceptional, (7)
"So cozy so nice so affordable! Jenna was a dream to work with! We will be back!"
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

Cozy Lake House On The Channel With Access To 5 Lakes!

9.6 out of 10, Exceptional, (39)
"It was a nice and peaceful place. Was a little dirty but we still ejoyed our stay."
The price is NZ$508
includes taxes & fees
27 Oct - 28 Oct
Cozy Lake House On The Channel With Access To 5 Lakes!
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 Middlebury Hotel Reviews

Find out more about Middlebury

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$250 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 Deutsch Kase Haus, 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 shopping and gardens during your trip.

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

Charming 3-bedroom house located on Main Street in Downtown Middlebury: This highly rated holiday home rental in Middlebury has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals will I find in Middlebury?

With 17 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlebury stay.

What can I see and do in Middlebury?

Stone Lake and Hunter Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Meadow Valley Golf Club and Middlebury Public Library are other places worth a visit.

What are holiday rentals like in Middlebury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebury. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.