Middlebury Vacation Homes

A lakeside scene with a wooden dock, a blue canoe, and a rocky shoreline.

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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!

Middlebury

carol m.

HK$3,462 total

includes taxes & fees

16 Sept - 17 Sept

A modern kitchen with a central island, stainless steel appliances, and a large window.

2. Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

Middlebury

Page E.

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

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

Ripton

Lani C.

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

4. Beautiful home located in the Mad River Valley

Warren

Melissa P.

5. Little City Big Heart

Vergennes

Patsy H.

HK$2,414 total

includes taxes & fees

21 Sept - 22 Sept

A rustic cabin surrounded by autumn foliage.

6. Beautiful home located in the Mad River Valley

Warren

Allie T.

7. Beautiful home located in the Mad River Valley

Warren

Sloan S.

A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

8. Studio in the country w/Hot Tub

Monkton

HK$2,024 total

includes taxes & fees

23 Sept - 24 Sept

A room with a large window overlooking a deck with two chairs and a table.

9. Luxurious Vermont home minutes from Sugarbush Resort

Warren

Noah S.

A wooden interior with large windows, a dining table, chairs, and a sofa.

10. Beautiful timber frame just minutes to Middlebury!

New Haven

"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...

Suzanne L.

HK$7,657 total

includes taxes & fees

22 Sept - 23 Sept

A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

11. Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

East Warren

Daniel B.

A two-story house with a covered porch, outdoor seating, and a lawn.

12. Classic Vermont Farmhouse near Sugarbush Resort

Warren

Peggy V.

A modern living room with a fireplace, a sofa, a coffee table, and a white door.

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

Crown Point

Phillip K.

HK$3,129 total

includes taxes & fees

13 Sept - 14 Sept

A deck with chairs overlooking a mountainous landscape.

14. Gorgeous Mountain Home Near Mad River Glen

Fayston

Nerissa B.

A wooden staircase leading to a dock by a lake surrounded by trees.

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

Leicester

Eric A.

A modern living room with a sofa, coffee table, and a flat-screen TV mounted on the wall.

16. The Hinesburg Hideaway Unit 3

Hinesburg

HK$1,497 total

includes taxes & fees

30 Sept - 1 Oct

A wooden deck leading to a cabin with a stone foundation, surrounded by a forest with autumn foliage.

17. Large Vermont ski home on private scenic lot centrally located in the Mad River Valley

Waitsfield

Heather Bello T.

A log cabin interior with a stone fireplace, a sofa set, a round table, and a large window offering a view of the outdoors.

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

Waitsfield

lauren m.

A kitchen with wooden beams, a central island, and a view of a snowy outdoor area.

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

Fayston

Anonymous traveller

HK$4,752 total

includes taxes & fees

23 Sept - 24 Sept

A wooden deck with a metal railing, black plastic chairs, and a large window overlooking a forested area.

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

Ticonderoga

"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...

patricia A.

HK$1,577 total

includes taxes & fees

17 Sept - 18 Sept

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Top Middlebury Hotel Reviews

Middlebury Inn

8/10 Good

"Thank you!"

Super 8 by Wyndham Ticonderoga

8/10 Good

"I di not rate the amenities because there really were none. The staff were very helpful and prompt when we called. The TV and remote did not work when we first went to the room. I called the front desk, and the gentleman was there immediately. There had been a full power outage the night before and just had to make an adjustment on the TV. He was apologetic and friendly. The coffee was readily available located by the front desk. Clean room, Made the 2 nights stay comfortable, close to town and Fort Ticonderoga. Parking is located right out the front entrance"

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