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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 historic town with a river, buildings with traditional architecture, and a waterfall.

1. *Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
9.6 out of 10, Exceptional, (11 reviews)
"fantastic!"
United States
Diana L.
*Downtown Middlebury Waterfall Studio Apartment*
A modern kitchen with white cabinets, a coffee machine, and a wooden accent wall.

2. 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 $116
CA $308 total
includes taxes & fees
Nov 9 - Nov 10
Charming one bedroom just minutes to Middlebury!
A modern kitchen with stainless steel appliances, a granite countertop, and pendant lighting.

3. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is CA $165
CA $408 total
includes taxes & fees
Nov 9 - Nov 10
Gracious two bedroom just minutes to Middlebury!
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

4. 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 $188
CA $280 total
includes taxes & fees
Nov 22 - Nov 23
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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 $154
CA $394 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 $192
CA $483 total
includes taxes & fees
Nov 9 - Nov 10
Purple Door Cottage in the heart of Middlebury!
A snow-covered house with a lit entrance and a small outdoor light feature.

7. 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 $126
CA $307 total
includes taxes & fees
Nov 9 - Nov 10
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A lakeside view with a fire pit and chairs, surrounded by mountains and trees.

8. Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (82 reviews)
"Awesome place. We will be back!"
United States
Christopher T.
The price is CA $254
CA $353 total
includes taxes & fees
Nov 9 - Nov 10
Doc's Lake house 1st floor, 2 bedroom apartment
A red barn in a forested area with mountains in the background.

9. 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 $324
CA $394 total
includes taxes & fees
Nov 28 - Nov 29
Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
A wooden table with a bottle of wine, glasses, and grapes.

10. 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 $365
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

11. 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 CA $365
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Inviting timber frame cabin in Vermont's Green Mountains
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 CA $365
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $365
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Cozy and pristine timberframe cabin
A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

14. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is CA $218
CA $360 total
includes taxes & fees
Nov 9 - Nov 10
Studio in the country w/Hot Tub
A building with a sign for 'SQUARES Café' offering breakfast, lunch, and dinner.

15. 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 $382
CA $647 total
includes taxes & fees
Nov 16 - Nov 17
Little City Big Heart
A wooden staircase leading to a covered outdoor area with a view of a green lawn and trees.

16. 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 $264
CA $663 total
includes taxes & fees
Nov 16 - Nov 17
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
A spacious dining area with a long table set for six, large windows offering a view of the outdoors, and a wooden ceiling structure.

17. 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 $542
CA $1,133 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful timber frame just minutes to Middlebury!
A balcony with a view of a green landscape and mountains.

18. Mountain View Cottage

Mountain View Cottage
Bristol
The price is CA $437
CA $516 total
includes taxes & fees
Nov 10 - Nov 11
Mountain View Cottage
A lakeside house with a dock, surrounded by dense trees.

19. 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 $578
CA $1,099 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.

20. 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 $480
CA $1,044 total
includes taxes & fees
Nov 10 - Nov 11
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
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

A white building with green shutters and a sign that reads "Storeham Inn."
Shoreham Inn

Shoreham Inn

Shoreham Inn
Shoreham

10/10 Excellent

The owners were incredibly hospitable, the place is charming and cozy, it felt extremely welcoming
Canada
Shelley
Reviewed August 5, 2026
Shoreham Inn

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 $115 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.