A wooden pier extending into a lake, surrounded by lush greenery and a prominent lighthouse on a small island.

Holiday Homes in Middlebury

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middlebury holiday homes

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

1. Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home in a great location. Very comfortable and we had a great stay"
United States
carol m.
The price is AU$609
includes taxes & fees
26 Oct - 27 Oct
Purple Door Cottage in the heart of Middlebury!
A wooden interior with large windows, a dining table, chairs, and a sofa.

2. Beautiful timber frame just minutes to Middlebury!

Beautiful timber frame just minutes to Middlebury!
New Haven
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Suzanne L.
The price is AU$1,282
includes taxes & fees
26 Oct - 27 Oct
Beautiful timber frame just minutes to Middlebury!
A bedroom with a bed, bedside table, lamp, and a ceiling fan.

3. Little City Big Heart

Little City Big Heart
Vergennes
10.0 out of 10, Exceptional, (45 reviews)
"Great house we enjoyed it"
United States
Patsy H.
The price is AU$633
includes taxes & fees
6 Oct - 7 Oct
Little City Big Heart
A rustic cabin surrounded by autumn foliage.

4. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

5. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.0 out of 10, Wonderful, (12 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
Beautiful home located in the Mad River Valley
A room with a large window overlooking a forest in autumn.

6. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (49 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
A modern living room with a fireplace, a sofa, a coffee table, and a white door.

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

Beautiful Lake House with whole house renovation & fresh modern appeal!
Crown Point
9.8 out of 10, Exceptional, (13 reviews)
"Awesome place with incredible lake views! The host was very attentive and thoughtful about our needs. I highly recommend!"
United States
Phillip K.
The price is AU$555
includes taxes & fees
12 Oct - 13 Oct
Beautiful Lake House with whole house renovation & fresh modern appeal!
A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

8. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is AU$375
includes taxes & fees
3 Nov - 4 Nov
Studio in the country w/Hot Tub
A wooden cabin interior with a staircase leading to a balcony, large windows, and a view of a snowy forest.

9. Large multi-family ski home located on the slopes of Sugarbush Resort

Large multi-family ski home located on the slopes of Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (31 reviews)
"The skiing was fantastic. Thanks for a great stay."
United States
James K.
Large multi-family ski home located on the slopes of Sugarbush Resort
A room with a large window overlooking a deck with two chairs and a table.

10. Luxurious Vermont home minutes from Sugarbush Resort

Luxurious Vermont home minutes from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (44 reviews)
"Perfect location for ski vacation. House was clean, close to resort. Quick drive to restaurants, looking forward to staying again! "
United States
Noah S.
Luxurious Vermont home minutes from Sugarbush Resort
A wooden staircase leading to a dock by a lake surrounded by trees.

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

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Leicester
10.0 out of 10, Exceptional, (1 review)
"Everything was spectacular! Fern Lake is peaceful and breathtaking. Lake house was wonderful, and amazing. It was spacious, yet homie."
United States
Eric A.
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
A two-story house with a covered porch, outdoor seating, and a lawn.

12. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.6 out of 10, Exceptional, (57 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
Classic Vermont Farmhouse near Sugarbush Resort
A lakeside setting with a fire pit and a bench near the water.

13. Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets

Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
Bridport
10.0 out of 10, Exceptional, (3 reviews)
"the home was very clean, plenty of space, there were many amenities which may the stay very pleasant."
United States
Robert H.
The price is AU$1,259
includes taxes & fees
4 Oct - 5 Oct
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
A log cabin interior with a stone fireplace, a sofa set, a round table, and a large window offering a view of the outdoors.

14. Ridge House - Modern Log Home Nestled on top of a Private Mountain

Ridge House - Modern Log Home Nestled on top of a Private Mountain
Waitsfield
10.0 out of 10, Exceptional, (17 reviews)
"A gorgeous house, well designed, incredibly comfortable & perfectly appointed. Responsive staff at the mgmt company too. We will be back!"
United States
lauren m.
Ridge House - Modern Log Home Nestled on top of a Private Mountain
A modern living room with a sofa, coffee table, and a flat-screen TV mounted on the wall.

15. The Hinesburg Hideaway Unit 3

The Hinesburg Hideaway Unit 3
Hinesburg
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and spacious, quick communication with host."
United States
Tina C.
The price is AU$268
includes taxes & fees
14 Oct - 15 Oct
The Hinesburg Hideaway Unit 3
A wooden deck with a metal railing, black plastic chairs, and a large window overlooking a forested area.

16. Glamping Escape House - reconnect with nature without giving up comfort.

Glamping Escape House - reconnect with nature without giving up comfort.
Ticonderoga
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed a three night stay with family. The listing is very accurate. This is glamping. If that is what you are expecting you should be delighted. Some nice additional highlights were an ample source of firewood, nice swings, a battery operated fan. Also, the shower was a pleasant surprise. I was not expecting a hot shower. It is a great system. I would say it provides about a one yard reservoir providing heated water. Very nice. Hosts were very helpful and went above and beyond to...
United States
patricia A.
The price is AU$287
includes taxes & fees
15 Oct - 16 Oct
Glamping Escape House - reconnect with nature without giving up comfort.
A deck with chairs overlooking a mountainous landscape.

17. Gorgeous Mountain Home Near Mad River Glen

Gorgeous Mountain Home Near Mad River Glen
Fayston
10.0 out of 10, Exceptional, (18 reviews)
"Stuga was a great find for our extended family. The house was recently renovated and in addition to high-end finishes, everything had been updated, so the place felt clean, comfortable, and well-appointed."
United States
Nerissa B.
The price is AU$1,124
includes taxes & fees
6 Oct - 7 Oct
Gorgeous Mountain Home Near Mad River Glen
An outdoor seating area with wicker chairs and a small table, surrounded by lush greenery and trees.

18. Entire Enchanting, Light-Filled 1830 Farmhouse

Entire Enchanting, Light-Filled 1830 Farmhouse
Waitsfield
9.8 out of 10, Exceptional, (10 reviews)
"We came up to Vermont for a wedding and the "farm house" was just what we needed. Thank you! Much appreciated the easy check in and allowing us to arrive a bit earlier to get ready for the wedding bash. P. Murray"
United States
Patti M.
The price is AU$1,015
includes taxes & fees
8 Oct - 9 Oct
Entire Enchanting, Light-Filled 1830 Farmhouse
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

19. Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Hancock
10.0 out of 10, Exceptional, (1 review)
"The maple castle was awesome! Definitely the most unique house I have ever stayed in. You can sit in the hot tub and watch the river or you can walk down a tiny hill to tie up a tube and float in it. The owners were extremely helpful and responsive. Would definitely recommend. "
United States
Katie H.
The price is AU$2,070
includes taxes & fees
25 Oct - 26 Oct
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
A kitchen with wooden beams, a central island, and a view of a snowy outdoor area.

20. Light-filled retreat in Mad River Valley with internet & deck

Light-filled retreat in Mad River Valley with internet & deck
Fayston
8.8 out of 10, Excellent, (6 reviews)
"Enjoyed the comfortable home. Had just about everything we needed for our stay. Loved the location and the view was great. Close to things we wanted to do and see."
United States
Anonymous traveller
The price is AU$865
includes taxes & fees
26 Oct - 27 Oct
Light-filled retreat in Mad River Valley with internet & deck
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

Brandon Inn

Brandon Inn

8/10 Good
"This lovely inn is a unique experience. I loved the building and furnishings, and my dog and I enjoyed exploring the garden area. The people were helpful and friendly, and breakfast was nice. I did have a little trouble with the electronic lock on the door to my room, but was eventually able to get in each time. Also, I couldn’t find a remote for the TV in the room, and when I called the phone number for assistance, the voice mailbox was full so I couldn’t leave a message. I didn’t care that much about watching TV so I didn’t bother to follow up."
Aleta 1-night trip
Posted 3 hours ago
Brandon Inn

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews
337
Accommodation
301 Holiday Homes
Lowest Price
AU$268
Highest Price
AU$2,070