Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (180)
"Our goal was to unplug a bit, play games, watch movies and explore a new VT town during our 2 night stay. Our expectations were fully met! We enjoyed spending a day in Middlebury and all of our time in the cabin. It was nice to have wifi access as well! We look forward to coming back during the warmer weather! "
The price is AU$292
includes taxes & fees
21 Jan - 22 Jan
Ultimate relaxing vacation

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

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Pristene lakefront property - charming, quiet, and rustic for nature lovers.

8.0 out of 10, Very good, (71)
"Plenty of room for the whole family."
Pristene lakefront property - charming, quiet, and rustic for nature lovers.

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

9.6 out of 10, Exceptional, (41)
"Amazing view from the back deck, very clean home, plenty of room for our family of 6. Will definitely be staying here again next time we're in Lake George!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

10.0 out of 10, Exceptional, (175)
"Absolutely perfect location for what we were looking for! Beautiful view of the Lake Champlain and the house was perfect and comfortable- it had everything we needed! Peaceful and relaxing right before Christmas. "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

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

10.0 out of 10, Exceptional, (60)
"Beautiful area… had everything we needed! Loved the quiet."
The price is AU$350
includes taxes & fees
21 Jan - 22 Jan
Doc's Lake house 1st floor, 2 bedroom apartment

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (139)
"Such a great cozy mountain cabin with a beautiful stone fireplace well stocked with plenty of dry wood and kindling- all that’s needed for the perfect après-ski setting. Add a glass of wine to the host-provided Vermont cheese and crackers and you’re set for the evening. Initially concerned that the cabin was right on Rte 100 but very quiet and peaceful. Never heard any road noise. The two loft bedrooms are comfortable and functional accessed by ladder. Not a place for those with mobility...
The price is AU$754
includes taxes & fees
22 Jan - 23 Jan
Stetson Hollow Cabin by Stetson Brook

Dog-friendly cottage on acreage with nearby creek & wood stove

9.0 out of 10, Wonderful, (55)
"The house was cute, and the location was good. We liked the woods and stream around the house and the quiet road it was on. The views of the woods out the windows were lovely. There were a few old board games for the kids, but not much else for them to do when it was raining. The TV worked well, and we had internet. The bed downstairs was a little hard and the sheets looked old. Some of the furniture was obviously old, but we didn't use a lot of it anyway. The kids stayed in the loft and...
Dog-friendly cottage on acreage with nearby creek & wood stove

Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

9.2 out of 10, Wonderful, (114)
"Amazing "
Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

8.4 out of 10, Very good, (65)
"Tried to plunge the toilet without success. Was quiet peaceful and comfortable "
The price is AU$435
includes taxes & fees
20 Jan - 21 Jan
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony

Moose Lodge - Rustic and Cozy

9.8 out of 10, Exceptional, (48)
"The property was great. The neighbors that we were lucky enough to meet are very nice. The house was clean and very well maintained. I definitely would rent from Nicholas again. "
Moose Lodge - Rustic and Cozy

Ski Lodge Mtn Retreat w/ Fire Pit, Deck & Views!

10.0 out of 10, Exceptional, (25)
"We returned to the same cabin 3 years later. In addition to swimming and hiking right at the property, we took an afternoon trip to Stowe and another to Burlington. Back at the cabin, we enjoyed a family fun night playing pool, air hockey, darts, and cornhole in the basement. We also cooked several meals in the well stocked kitchen. The cabin serves as a comfortable home base to explore Vermont!"
Ski Lodge Mtn Retreat w/ Fire Pit, Deck & Views!

Cozy Lake Champlain Cottage w/ Beautiful View

9.6 out of 10, Exceptional, (24)
"We enjoyed our stay very much!! especially the views of the fall foliage on the mountains across the lake!!! everything was nice and clean and very convenient!! Firewood was also provided!!!"
Cozy Lake Champlain Cottage w/ Beautiful View

Ski getaway near the slopes with private balcony & mountain views

8.8 out of 10, Excellent, (16)
"Beautiful spot "
The price is AU$521
includes taxes & fees
20 Jan - 21 Jan
Ski getaway near the slopes with private balcony & mountain views

Beautiful lodge with furnished deck and views - near skiing

10.0 out of 10, Exceptional, (119)
"Beautiful views, private setting, great location to skiing, well-stocked professional kitchen, gas fireplace, plenty of room to spread out. Very good communication with management company. Would stay here again."
Beautiful lodge with furnished deck and views - near skiing

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (106)
"Beautiful area for short 4 day stay . Cabin was clean and cozy. Well stocked for pretty much anything . Only dislike was the bedroom was in a loft area with narrow steps , and a bit tough to navigate in the middle of the night when the restroom was needed . Loved the quaintness otherwise . "
Classic Vermont Cabin on 2.5 acres Lake Frontage

Sugarbush Tiny House/Cabin on 3.2 Acres at the base of Sugarbush-Mount Ellen

10.0 out of 10, Exceptional, (48)
"Cute house, neat and tidy both inside and out. All the conveniences of home tucked away inside. The sofa bed was comfortable, and the shower area was spacious. The host responded quickly to any questions. Great location within a couple miles of the town itself. We had a great stay!"
Sugarbush Tiny House/Cabin on 3.2 Acres at the base of Sugarbush-Mount Ellen

Picturesque mountain view condo with fireplace, balcony, deck, pool, & kitchen

9.0 out of 10, Wonderful, (13)
"We enjoyed the coziness after a few days on the slopes. Lots of small restaurants and shops to explore. "
Picturesque mountain view condo with fireplace, balcony, deck, pool, & kitchen

Cozy Cottage on Beautiful Lake Champlain.

9.6 out of 10, Exceptional, (169)
"My husband and I really enjoyed staying at this darling cottage, on the bay in Lake Champlain. We brought our lab with us and she loved being outside here. "
Cozy Cottage on Beautiful Lake Champlain.
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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Other types of properties in Middlebury you may be interested in

Middlebury Inn

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Solid, comfortable and walkable to town and campus. "
The price is AU$256
includes taxes & fees
20 Jan - 21 Jan
Middlebury Inn

Courtyard Middlebury

3.0 star property
8.8 out of 10, Excellent, (489)
"Very conveniently located and easy parking. While somewhat understaffed, the staff were friendly and as responsive as they could be. Our fireplace switch didn't work but they came and tried to fix it. When our son decided to stay with us in our room, they easily accommodated us with a rollaway bed. One definite need for improvement: the pillows. They hold no shape and I needed 3 to be comfortable. "
The price is AU$246
includes taxes & fees
26 Jan - 27 Jan
Courtyard Middlebury

Waybury Inn

3.5 star property
9.2 out of 10, Wonderful, (69)
"Online it says it has an EV charging station but it doesn't. But not too much of a setback otherwise the place was very cute and hospitable! Great Vermont charm! "
Waybury 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.

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?

Pristene lakefront property - charming, quiet, and rustic for nature lovers.: This holiday home rental outside of Middlebury is located on a lake, and has a fireplace, a balcony 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 garden.

How many holiday rentals are there in Middlebury?

Expedia has 14 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 Danforth Pewter is just one of the family-friendly sights. Other places in town to visit include UVM Morgan Horse Farm and Halpin Covered Bridge.

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.