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Addison County Vacation Rentals

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Top cities in Addison County

A river with a waterfall, a stone bridge, and buildings in the background.
Vacation Rentals

Middlebury

Middlebury

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
The price is CA $115
CA $305 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $125
CA $292 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $186
CA $270 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $170
CA $411 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $159
CA $399 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $196
CA $484 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $362
CA $472 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $321
CA $391 total
includes taxes & fees
Nov 28 - Nov 29
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 CA $217
CA $357 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $362
CA $472 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $362
CA $472 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $272
CA $671 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $362
CA $472 total
includes taxes & fees
Nov 8 - Nov 9
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.
The price is CA $379
CA $642 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $433
CA $512 total
includes taxes & fees
Nov 11 - Nov 12
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.
The price is CA $464
CA $1,035 total
includes taxes & fees
Nov 9 - Nov 10
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.
The price is CA $573
CA $1,091 total
includes taxes & fees
Dec 1 - Dec 2
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.
The price is CA $476
CA $1,036 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $840
CA $1,443 total
includes taxes & fees
Dec 3 - Dec 4
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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Find vacation rentals that suit your style

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Apartments

Top Addison County Hotel Reviews

A two-story house with a porch, a fountain, and a flag.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast
Poultney

10/10 Excellent

Beautiful old building, well-maintained, filled with vintage furniture and collectable items. Like staying in a museum. Owners are very friendly and helpful. Breakfast was great.
Canada
Lloyd
Reviewed July 26, 2026
Bentley House Bed and Breakfast

Find out more about Addison County

Everything you need to know about Addison County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Addison County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Addison County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Addison County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Addison County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Addison County vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Addison County rentals

At Expedia, we put the best Addison County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Addison County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Addison County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Addison County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.