Holiday Rentals in Addison County

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Our top choices for Addison County holiday rentals

Outdoor dining

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

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is €150
includes taxes & fees
23 Jul - 24 Jul
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Interior

Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes

Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes
Bristol
9.8 out of 10, Exceptional, (23 reviews)
"Host and tiny house were fantastic!"
United States
Peter D.
The price is €161
includes taxes & fees
20 Jul - 21 Jul
Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes
Fridge, microwave, oven, stovetop

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, (79 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is €179
includes taxes & fees
28 Jun - 29 Jun
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Exterior detail

Charming one bedroom just minutes to Middlebury!

Charming one bedroom just minutes to Middlebury!
New Haven
The price is €200
includes taxes & fees
24 Jun - 25 Jun
Charming one bedroom just minutes to Middlebury!
Exterior

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
The price is €265
includes taxes & fees
25 Jun - 26 Jun
Robert Frost Mountain Cabins
Interior

Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is €283
includes taxes & fees
24 Jun - 25 Jun
Tasteful two bedroom just minutes to Middlebury!
Property grounds

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, (4 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 €443
includes taxes & fees
24 Jul - 25 Jul
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Golf

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
The price is €352
includes taxes & fees
30 Jun - 1 Jul
Purple Door Cottage in the heart of Middlebury!
Exterior detail

Downtown Middlebury 3 BR Home - Walk Everywhere!

Downtown Middlebury 3 BR Home - Walk Everywhere!
Middlebury
9.6 out of 10, Exceptional, (32 reviews)
"Great location, very clean"
United States
Karyn M.
The price is €326
includes taxes & fees
8 Jul - 9 Jul
Downtown Middlebury 3 BR Home - Walk Everywhere!
Shower, hair dryer, towels, soap

Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is €229
includes taxes & fees
7 Jul - 8 Jul
Studio in the country w/Hot Tub
Exterior

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 €374
includes taxes & fees
24 Jun - 25 Jun
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Interior

Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is €313
includes taxes & fees
29 Jun - 30 Jun
Gracious two bedroom just minutes to Middlebury!
Exterior

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 €351
includes taxes & fees
24 Jun - 25 Jun
Cozy and pristine timberframe cabin
Smart TV, fireplace, DVD player, books

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 €374
includes taxes & fees
9 Jul - 10 Jul
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Interior

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, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Fridge, microwave, oven, stovetop

Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
Middlebury
10.0 out of 10, Exceptional, (78 reviews)
"Lovely property. Will stay again."
United States
Patricia Y.
The price is €660
includes taxes & fees
15 Jul - 16 Jul
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
Interior

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 €837
includes taxes & fees
24 Jun - 25 Jun
Beautiful timber frame just minutes to Middlebury!
Outdoor dining

The Tacklebox on Lake Champlain, Sauna & Hot Tub, near Middlebury

The Tacklebox on Lake Champlain, Sauna & Hot Tub, near Middlebury
Bridport
10.0 out of 10, Exceptional, (11 reviews)
"We had an amazing time staying at the Tacklebox! The main cabin and bunkhouse were very cozy to sleep in, and we had an incredible view of Lake Champlain. We’ll definitely have to come back in the summer when the lake has thawed. The sauna and hot tub were also very relaxing, would highly recommend for anyone looking for a fun place to vacation in Vermont!"
United States
Luke T.
The price is €929
includes taxes & fees
22 Jul - 23 Jul
The Tacklebox on Lake Champlain, Sauna & Hot Tub, near Middlebury
Terrace/patio

Modern Waterfront Lakehouse sleeps 8, Dock, Mountain Views & Close to Middlebury

Modern Waterfront Lakehouse sleeps 8, Dock, Mountain Views & Close to Middlebury
Salisbury
9.8 out of 10, Exceptional, (26 reviews)
"Great house and great host!"
United States
Joe N.
Modern Waterfront Lakehouse sleeps 8, Dock, Mountain Views & Close to Middlebury
Terrace/patio

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, (1 review)
"This house has literally everything you would ever need. Even had a pack n play, kids towels, baby wipes, and a kids play mat. Would be nice to stay in warmer months to enjoy the lake."
United States
Nicholas A.
The price is €816
includes taxes & fees
12 Jul - 13 Jul
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
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
"What a great place to stay. Helpful staff and the inn is well maintained and clean. Love to come back next year for your 200th birthday"
Belinda 5-night trip
Posted less than an hour ago
Middlebury Inn

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Holiday Homes in Addison County

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