A multi-tiered waterfall surrounded by dense forest.

Holiday Rentals in Addison County

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Our top choices for Addison County holiday rentals

A modern kitchen with white cabinets, a coffee machine, and a wooden accent wall.

1. Charming one bedroom just minutes to Middlebury!

Charming one bedroom just minutes to Middlebury!
New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Lovely unit, clean, well equipped, quiet location"
United States
Jane
The price is €197
includes taxes & fees
8 Nov - 9 Nov
Charming one bedroom just minutes to Middlebury!
A snow-covered house with a lit entrance and a small outdoor light feature.

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, (10 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is €196
includes taxes & fees
7 Nov - 8 Nov
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

3. 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, (97 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 €179
includes taxes & fees
22 Nov - 23 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A modern kitchen with stainless steel appliances, a granite countertop, and pendant lighting.

4. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is €327
includes taxes & fees
2 Dec - 3 Dec
Gracious two bedroom just minutes to Middlebury!
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

5. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is €357
includes taxes & fees
20 Nov - 21 Nov
Tasteful two bedroom just minutes to Middlebury!
A large grassy field with a historic building in the background.

6. 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 €307
includes taxes & fees
9 Nov - 10 Nov
Purple Door Cottage in the heart of Middlebury!
A wooden table with a bottle of wine, glasses, and grapes.

7. 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 €302
includes taxes & fees
8 Nov - 9 Nov
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A red barn in a forested area with mountains in the background.

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

Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
Ripton
9.8 out of 10, Exceptional, (7 reviews)
"The property was very generously provisioned, pet friendly, clean and comfortable."
United States
Lani C.
The price is €247
includes taxes & fees
28 Nov - 29 Nov
Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

9. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is €230
includes taxes & fees
8 Nov - 9 Nov
Studio in the country w/Hot Tub
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

10. 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 €287
includes taxes & fees
15 Nov - 16 Nov
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

11. 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 €302
includes taxes & fees
8 Nov - 9 Nov
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A wooden staircase leading to a covered outdoor area with a view of a green lawn and trees.

12. 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)
"A wonderful property in a great location especially if you are leisurely driving the VT 100 scenic byway."
United States
Kevin J.
The price is €431
includes taxes & fees
9 Nov - 10 Nov
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
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 €302
includes taxes & fees
8 Nov - 9 Nov
Cozy and pristine timberframe cabin
A building with a sign for 'SQUARES Café' offering breakfast, lunch, and dinner.

14. Little City Big Heart

Little City Big Heart
Vergennes
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful home,very family friendly. The host is very welcoming and easy to get in contact with. Would recommend this property to family and friends."
United States
Craig S.
Little City Big Heart
A balcony with a view of a green landscape and mountains.

15. Mountain View Cottage

Mountain View Cottage
Bristol
The price is €333
includes taxes & fees
10 Nov - 11 Nov
Mountain View Cottage
A bedroom with a large window, a bed with a white duvet, a blue pillow, and a framed picture on the wall.

16. 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.
Beautiful timber frame just minutes to Middlebury!
A lakeside house with a dock, surrounded by dense trees.

17. 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.
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
A wooden staircase leading to a dock by a lake surrounded by trees.

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

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Leicester
8.0 out of 10, Very good, (2 reviews)
"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 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 €932
includes taxes & fees
3 Dec - 4 Dec
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

Green Mountain Inn

Green Mountain Inn

10/10 Excellent
"Very cozy and warm. Beds were amazing and the food was great. Highly recommend this cute little hotel."
Kimberly 1-night trip
Posted 12 hours ago
Green Mountain Inn

Find out more about Addison County

Holiday Homes in Addison County

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