A multi-tiered waterfall surrounded by dense forest.

Vacation Rentals in Addison County

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Our top choices for Addison County vacation rentals

A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (96 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is ￥22,434
￥34,296 total
includes taxes & fees
Oct 18 - Oct 19
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A wooden deck with blue chairs and a barbecue grill.

2. Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.4 out of 10, Exceptional, (9 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is ￥14,011
￥35,969 total
includes taxes & fees
Oct 11 - Oct 12
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A wooden cabin with a snow-covered roof, surrounded by trees and snow.

3. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (43 reviews)
"Very nice place great owner"
United States
Joe
The price is ￥55,489
￥60,483 total
includes taxes & fees
Oct 8 - Oct 9
Robert Frost Mountain Cabins
A large grassy field with a historic building in the background.

4. 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 ￥32,089
￥69,356 total
includes taxes & fees
Oct 27 - Oct 28
Purple Door Cottage in the heart of Middlebury!
A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a living room with a sofa.

5. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is ￥34,106
￥67,751 total
includes taxes & fees
Nov 2 - Nov 3
Gracious two bedroom just minutes to Middlebury!
A living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has white walls and a blue carpet.

6. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is ￥31,350
￥62,717 total
includes taxes & fees
Nov 2 - Nov 3
Tasteful two bedroom just minutes to Middlebury!
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

7. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is ￥47,437
￥63,755 total
includes taxes & fees
Oct 8 - Oct 9
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
A wooden table with a bottle of wine, glasses, and grapes.

8. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (13 reviews)
"It is a beautiful location in a fully equipped cabin off the beaten path."
United States
Steven
The price is ￥40,449
￥55,299 total
includes taxes & fees
Nov 2 - Nov 3
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A bedroom with a bed, bedside table, lamp, and a ceiling fan.

9. 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 ￥37,714
￥70,692 total
includes taxes & fees
Oct 6 - Oct 7
Little City Big Heart
A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

10. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is ￥23,378
￥40,467 total
includes taxes & fees
Oct 12 - Oct 13
Studio in the country w/Hot Tub
A wooden staircase leading to a covered outdoor area with a view of a green lawn and trees.

11. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is ￥29,613
￥77,070 total
includes taxes & fees
Oct 7 - Oct 8
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

12. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is ￥40,449
￥55,299 total
includes taxes & fees
Nov 2 - Nov 3
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

13. Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is ￥40,449
￥55,299 total
includes taxes & fees
Nov 2 - Nov 3
Cozy and pristine timberframe cabin
A wooden interior with large windows, a dining table, chairs, and a sofa.

14. 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 ￥72,586
￥149,220 total
includes taxes & fees
Oct 26 - Oct 27
Beautiful timber frame just minutes to Middlebury!
A wooden staircase leading to a dock by a lake surrounded by trees.

15. 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.
The price is ￥53,496
￥113,903 total
includes taxes & fees
Oct 5 - Oct 6
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
A lakeside setting with a fire pit and a bench near the water.

16. 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 ￥68,860
￥140,952 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

17. Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, charming, and very clean cabin with excellent communication with team and fun access to trails, hot tub and game room."
United States
Kelly I.
The price is ￥40,449
￥55,299 total
includes taxes & fees
Nov 2 - Nov 3
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

18. Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views
Ripton
10.0 out of 10, Exceptional, (3 reviews)
"Our cabin was lovely—artfully built, well-stocked, perfectly clean, and very comfortable. We awoke to silence and a beautiful view of the mountains from our screened porch. We are already planning our return!"
United States
Sara S.
The price is ￥40,449
￥55,299 total
includes taxes & fees
Nov 2 - Nov 3
Immaculate mountain cabin with awe inspiring sunrise and mountain views
A wooden cabin with a snow-covered roof and a lit entrance.

19. Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is ￥50,837
￥67,107 total
includes taxes & fees
Oct 25 - Oct 26
Adorable cabin with screened porch and private fire pit
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

20. 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 ￥75,944
￥147,652 total
includes taxes & fees
Oct 4 - Oct 5
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
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 Addison County Hotel Reviews

Middlebury Inn

Middlebury Inn

10/10 Excellent
"Amazing!"
Fred 1-night trip
Posted 1 hour ago
Middlebury Inn

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