A multi-tiered waterfall surrounded by dense forest.

Vacation Rentals in Addison County

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Top Cities in Addison County

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

Middlebury

Middlebury

Our top choices for Addison County vacation 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
$199 nightly
The price is $210
Nov 8 - Nov 9
Total with taxes and fees
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
$186 nightly
The price is $208
Nov 8 - Nov 9
Total with taxes and fees
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
$176 nightly
The price is $197
Nov 22 - Nov 23
Total with taxes and fees
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
$268 nightly
The price is $284
Nov 9 - Nov 10
Total with taxes and fees
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
$268 nightly
The price is $284
Nov 9 - Nov 10
Total with taxes and fees
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.
$315 nightly
The price is $335
Nov 9 - Nov 10
Total with taxes and fees
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
$297 nightly
The price is $324
Nov 8 - Nov 9
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A hammock tied between trees with a view of a grassy field and 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.
$247 nightly
The price is $277
Nov 28 - Nov 29
Total with taxes and fees
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
$220 nightly
The price is $246
Nov 8 - Nov 9
Total with taxes and fees
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
$297 nightly
The price is $324
Nov 8 - Nov 9
Total with taxes and fees
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
$297 nightly
The price is $324
Nov 8 - Nov 9
Total with taxes and fees
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.
$422 nightly
The price is $473
Nov 9 - Nov 10
Total with taxes and fees
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.
$297 nightly
The price is $324
Nov 8 - Nov 9
Total with taxes and fees
Cozy and pristine timberframe cabin
A covered porch with outdoor furniture, a ceiling fan, and a wooden deck.

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.
$414 nightly
The price is $463
Nov 16 - Nov 17
Total with taxes and fees
Little City Big Heart
A balcony with a view of a green landscape and mountains.

15. Mountain View Cottage

Mountain View Cottage
Bristol
$331 nightly
The price is $371
Nov 10 - Nov 11
Total with taxes and fees
Mountain View Cottage
A spacious dining area with a long table set for six, large windows offering a view of the outdoors, and a wooden ceiling structure.

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.
$695 nightly
The price is $741
Nov 9 - Nov 10
Total with taxes and fees
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.
$695 nightly
The price is $778
Dec 1 - Dec 2
Total with taxes and fees
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.
$661 nightly
The price is $740
Nov 9 - Nov 10
Total with taxes and fees
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.
$922 nightly
The price is $1,033
Dec 3 - Dec 4
Total with taxes and fees
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
"The location was ideal - right in the center of the town area. The staff was very helpful to tell me what to do and where to eat - even had a list of restaurant options already printed1 I loved the "old timey" feel of my room, with a 4-poster bed, an electric fireplace, and Delft pottery accents around the room. If I'm ever back in Stowe, this is going to be my "go-to" place!"
Eliza 1-night trip
Posted 2 hours ago
Green Mountain Inn

Find out more about Addison County

Discover your perfect Addison County vacation rental with Expedia

How many vacation rentals are available in Addison County?


Expedia has plenty of vacation rentals to choose from in and around  Addison County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Addison County?


The selection of Addison County vacation rentals we have selected for you start as low as $187 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Addison County?


Vacation rentals in Addison County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Addison County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Addison County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Addison County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Addison County?


Find vacation rentals in Addison County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Addison County.  


What amenities are available in a vacation rental in Addison County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Addison County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Addison County?   


Everytime is a great time to head to Addison County! Staying in a Addison County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Addison County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Addison County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Addison County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Addison County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.