Middlebury Holiday Rentals

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Find properties with these dates

Tonight
May 1 - May 2
Tomorrow
May 2 - May 3
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Holiday Rentals in Middlebury

Cozy Loft for two with Hot Tub
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (190)
"For a getaway weekend this property and area is amazing."
Cozy Loft for two with Hot Tub
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (443)
"Excellent few nights at the cabin. The kids loved the spiral staircase, movie projector and hot tub. We loved exploring the area and the beauty of Vermont. This cabin has everything you need and I appreciated all the switch labels!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
3-bedroom cabin in welcoming Ticonderoga with WiFi. Clean & Economical
Private kitchen
3-bedroom cabin in welcoming Ticonderoga with WiFi. Clean & Economical
10.0 out of 10, Exceptional, (1)
"Great value, clean, quiet "
The price is AU$370
includes taxes & fees
5 May - 6 May
3-bedroom cabin in welcoming Ticonderoga with WiFi. Clean & Economical
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Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
Exterior
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
10.0 out of 10, Exceptional, (156)
"The house and property were just as advertised and the views from both floors were non-stop beautiful. Our dog loved the lapping of the water right at the end of the hill. It would be even more fun in the summer, I'm sure. The ping pong and pool tables in the basement were a lot of fun on a dreary day. Thank you Barb!"
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
Gorgeous home with amazing lake views, fireplace, firepit, hot tub, & balcony
Fridge, microwave, oven, stovetop
Gorgeous home with amazing lake views, fireplace, firepit, hot tub, & balcony
10.0 out of 10, Exceptional, (2)
Gorgeous home with amazing lake views, fireplace, firepit, hot tub, & balcony
Doc's Lake house 1st floor, 2 bedroom apartment
Exterior
Doc's Lake house 1st floor, 2 bedroom apartment
10.0 out of 10, Exceptional, (55)
"We really enjoyed staying at this cozy, well-equipped lake house. Everything was available to make the stay an enjoyable one. The driveway entrance and property were cleared for our arrival following a significant snowstorm. Communicating with the owner was a pleasure, with every a phone call or text message answered. Who would’ve thought seeing the solar eclipse of 2024 would be so easy and exciting! It was the owner and accommodations that made it all possible for planning the trip. We truly...
The price is AU$427
includes taxes & fees
3 May - 4 May
Doc's Lake house 1st floor, 2 bedroom apartment
Post and Beam Carriage House in the heart of Mad River Valley
Game room
Post and Beam Carriage House in the heart of Mad River Valley
10.0 out of 10, Exceptional, (26)
"Our group was an extended family reunion of sorts, including three adult siblings, each from different NE states, and one elementary aged child. We booked the carriage house for a fun weekend away to experience the 2024 Eclipse in the path of totality. The carriage house ended up being perfect for our needs. Cozy and charming, with great views. The well-stocked kitchen made mealtime a breeze, and the pool table was a huge bonus for our motley crew of kids-at-heart. Will definitely be back the...
Post and Beam Carriage House in the heart of Mad River Valley
Incredible Family Getaway Home With Boat Dock
Aerial view
Incredible Family Getaway Home With Boat Dock
10.0 out of 10, Exceptional, (120)
"Great location! Easy to book! We would love to come back :)"
Incredible Family Getaway Home With Boat Dock
Sugarbush Tiny House/Cabin on 3.2 Acres at the base of Sugarbush-Mount Ellen
Desk, free WiFi, bed sheets
Sugarbush Tiny House/Cabin on 3.2 Acres at the base of Sugarbush-Mount Ellen
10.0 out of 10, Exceptional, (46)
"We loved our stay at the Sugarbush Tiny House! It was the perfect location, close to great coffee, shops, and restaurants. Very close to outdoor recreation as well. The hosts were friendly and helpful. The property is stunning! We had everything we needed. Would definitely stay here again!"
Sugarbush Tiny House/Cabin on 3.2 Acres at the base of Sugarbush-Mount Ellen
Ultimate relaxing vacation
Ultimate relaxing vacation
9.8 out of 10, Exceptional, (151)
"Cozy, quiet, relaxing cabin stay. Home was clean and cozy. View of pond/lake was fantastic. We visited the first weekend of April. There area had snow a couple of days before our arrival. I would have spent a great deal of time on the back deck if the weather had been warmer. Looking forward to visiting again."
The price is AU$269
includes taxes & fees
7 May - 8 May
Ultimate relaxing vacation
Lakeside Cozy Quiet Heaven
Pool
Lakeside Cozy Quiet Heaven
9.8 out of 10, Exceptional, (116)
"Friendly and helpful host. Comfortable small cottage. Beautiful view."
Lakeside Cozy Quiet Heaven
Stetson Hollow Cabin by Stetson Brook
Living area
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (122)
"Stayed here to access the Sugarbush ski area. Easy 10-15 minute drive with on-site parking at cabin. Super cute with fire wood provided for use in both the inside fire place and outside fire pit. Cabin abuts the river which makes a nice coffee spot. Easy access to hiking trails. Only things to consider is that beds require climbing a ladder to access so keep that in mind if people have mobility issues. Also no TV so bring your own device if you have something you would like to watch."
The price is AU$699
includes taxes & fees
7 May - 8 May
Stetson Hollow Cabin by Stetson Brook
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook
Exterior
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook
9.8 out of 10, Exceptional, (37)
"Absolutely amazing trip for my husbands 35th birthday. The house was beautiful. Can’t wait to stay again."
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook
Classic Vermont Cabin on 2.5 acres Lake Frontage
Classic Vermont Cabin on 2.5 acres Lake Frontage
9.8 out of 10, Exceptional, (91)
"We can not say enough wonderful things about our stay. Brian was there to meet us and do a walk though of the property and even helped us out with local places to go. He is a gem! Although it rained it was absolutely perfect. The yard gave our pups a place to run free but there was also cute areas to walk them all around the area. The views of the water are incredible. Just sad it was too cold to jump in... maybe next time. October was the perfect time to see all the leaves changing and breathe...
Classic Vermont Cabin on 2.5 acres Lake Frontage
Private lake-front cabin with walk-in access to water, next to state park.
Smart TV, fireplace
Private lake-front cabin with walk-in access to water, next to state park.
9.8 out of 10, Exceptional, (38)
"This cabin was a cozy mid week get away for my wife and I. It was clean and well maintained. The lake and State park access were very convenient and we really enjoyed our hike through the park nature trail. It was only a short drive to either Castleton or Fair Haven, which had many conveniences. We would highly recommend this cabin to anyone looking for a quiet time away."
Private lake-front cabin with walk-in access to water, next to state park.
Ski home in the woods with a private hot tub, fireplace, & mountain views
Property grounds
Ski home in the woods with a private hot tub, fireplace, & mountain views
9.8 out of 10, Exceptional, (34)
"Super stay, really cool house, fantastic kitchen and big hot tub. Highly recommended"
Ski home in the woods with a private hot tub, fireplace, & mountain views
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK
Aerial view
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK
9.6 out of 10, Exceptional, (30)
"We had a great time in this clean, beautiful home!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK
Cozy Lake Champlain Cottage w/ Beautiful View
Fridge, microwave, stovetop, dishwasher
Cozy Lake Champlain Cottage w/ Beautiful View
9.6 out of 10, Exceptional, (14)
"Very cute lake house. Nicely updated, very clean. Good kitchen. Decent base if you want to see both Northern and Southern VT. We visited in April, when the lakefront was too flooded and the winds too chilly to enjoy the lake. Likely much prettier in the summertime!"
Cozy Lake Champlain Cottage w/ Beautiful View
Cozy Cottage on Beautiful Lake Champlain.
Property grounds
Cozy Cottage on Beautiful Lake Champlain.
9.6 out of 10, Exceptional, (159)
"Lakeside location was amazing! The deck is nice place to enjoy some coffee or a drink. The house is stocked with lots of fun activities like books/dvds/games. Overall great place for a cozy getaway! The space is on the smaller side so good for two people or three at most."
Cozy Cottage on Beautiful Lake Champlain.
Moose lodge near Lake George
Interior
Moose lodge near Lake George
9.6 out of 10, Exceptional, (45)
"We needed a place to stay close to our family and the house was in the perfect location. We loved the cleanliness, moose/lake decor and certainly the view of the lake. Nick was very easy to work with and the house had everything we needed!"
Moose lodge near Lake George
Don't see what you're looking for?
See all available properties in Middlebury
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.

Middlebury Holiday Home Travel Info

Number of holiday homes
9
Popular accommodation
Middlebury private holiday homes
Known landmarks
Lincoln Peak Vineyard, Town Hall Theatre and Otter Creek Brewing
International airport
Burlington, VT (BTV-Burlington Intl.)

Other types of properties in Middlebury you may be interested in

Waybury Inn
Interior
Waybury Inn
3.5 star property
9.4 out of 10, Exceptional, (62)
"What's not to like about a beautiful historic inn in central Vermont that was featured in the Bob Newhart show? It's well kept, and the staff are friendly and personable. I didn't get to try the food, but the restaurant is clearly popular."
The price is AU$240
includes taxes & fees
14 May - 15 May
Waybury Inn
Swift House Inn
Property grounds
Swift House Inn
3.0 star property
9.4 out of 10, Exceptional, (242)
"Fantastic! "
The price is AU$367
includes taxes & fees
2 May - 3 May
Swift House Inn
Middlebury Inn
Exterior
Middlebury Inn
3.0 star property
8.8 out of 10, Excellent, (1001)
"Great central location in town. Charming inn. "
The price is AU$253
includes taxes & fees
6 May - 7 May
Middlebury Inn
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.

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 favourite 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 depend 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 AU$269 per night. Entering your travel dates in the search wizard might find you 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 Danforth Pewter, 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?

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK: This holiday home rental outside of Middlebury is located on a lake, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Middlebury?

Expedia has 15 holiday rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include National Museum of the Morgan Horse and Holy Cow Inc., whereas Danforth Pewter is just one of the family-friendly sights. Other places in town to visit include Otter Creek Brewing 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.

Recent reviews of Middlebury properties
Expedia verified reviews

The Waitsfield Inn

The Waitsfield Inn

5/5 Excellent
"Quaint old Inn. Staff was great. Rooms were clean. Close to Norwich and surrounding towns. "
A verified traveller stayed at The Waitsfield Inn
Posted 2 days ago
The Waitsfield Inn