Middlebury Vacation Rentals

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Vacation Rentals in Middlebury

Beautiful 4-Bedroom Home beside Middlebury College

Beautiful 4-Bedroom Home beside Middlebury College

Middlebury, VT
Situated in Middlebury, this vacation home is within 1 mi (2 km) of Kevin P. Mahaney '84 Center for the Arts and Middlebury College. Vermont Folklife Center ...
Beautiful 4-Bedroom Home beside Middlebury College
Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Middlebury, VT
Located in the heart of Middlebury, this apartment building is within a 10-minute walk of National Museum of the Morgan Horse and Middlebury College. Town Hall ...
4.8/5 Exceptional! (8 reviews)
Great location!
"Great location and perfect place for relaxing a few days—or more—in this beautiful town."

Reviewed on Aug. 30, 2020

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!
Middlebury Home with Sunset views!

Middlebury Home with Sunset views!

Middlebury, VT
Situated in Middlebury, this apartment building is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse and ...
Middlebury Home with Sunset views!
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River House in Downtown Middlebury

River House in Downtown Middlebury

Middlebury, VT
The price is CA $315 per night from Nov 29 to Nov 29
This family-friendly Middlebury vacation home is located on a river, within 1 mi (2 km) of Henry Sheldon Museum of Vermont History and Middlebury College. National ...
River House in Downtown Middlebury
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

3.5 out of 5
2430 North Branch Road, Ripton, VT
The price is CA $348 per night from Nov 30 to Nov 30
Situated in Ripton, this cabin is within 9 mi (15 km) of Robert Frost Wayside Trail, Green Mountain National Forest, and Rikert Nordic Center. Middlebury College ...
5/5 Exceptional! (25 reviews)
"Wonderful cabin in the woods. The cabin was perfectly outfitted and so comfortable. The beds were cozy and the fireplace and candles made it so warm and inviting in the evenings. The easy and more adventurous trails added to the perfect outdoor experience. Nothing like it anywhere else! You will ..."

Reviewed on Sep. 19, 2020

Robert Frost Mountain Cabins
SPECIAL THIS WEEK SUGARBUSH SKI IN OUT 1963 CHALET COMPLETELY REMODELED 2021

SPECIAL THIS WEEK SUGARBUSH SKI IN OUT 1963 CHALET COMPLETELY REMODELED 2021

Warren, VT
Offering ski-in/ski-out access, this chalet in Warren is in the mountains, 1 mi (1.6 km) from Sugarbush Ski Resort, and close to winter activities such as cross-country ...
4.8/5 Exceptional! (97 reviews)
Nice place to stay
"The house is nice"

Reviewed on Oct. 25, 2021

SPECIAL THIS WEEK SUGARBUSH SKI IN OUT 1963 CHALET COMPLETELY REMODELED 2021
NEW! Heart of Sugarbush Village walk to Resort

NEW! Heart of Sugarbush Village walk to Resort

Warren, VT
Situated in the mountains, this condo building is 0.2 mi (0.3 km) from Sugarbush Ski Resort and within 6 mi (10 km) of Ole's Cross Country Center and Blueberry ...
4/5 Very Good! (2 reviews)
Warren getaway
"Very comfortable and spacious. Well equipped."

Reviewed on Nov. 11, 2021

NEW! Heart of Sugarbush Village walk to Resort
Stetson Hollow Cabin By Stetson Brook

Stetson Hollow Cabin By Stetson Brook

Warren, VT
The price is CA $288 per night from Dec 3 to Dec 3
Located in the mountains, this family-friendly cabin is within 6 mi (10 km) of Ole's Cross Country Center, Sugarbush Ski Resort, and Granville Gulf Reservation. ...
4.8/5 Exceptional! (57 reviews)
Great Cabin Getaway
"The cabin was lovely, and the property was beautiful, our host was great to work with and very informative of the surrounding area."

Reviewed on Nov. 24, 2021

Stetson Hollow Cabin By Stetson Brook
Ultimate Relaxing Vacation

Ultimate Relaxing Vacation

Fair Haven, VT
The price is CA $179 per night from Nov 29 to Nov 29
Located on the waterfront, this family-friendly cabin is within 12 mi (20 km) of Lake Hortonia, Mount Independence State Historic Site, and Halfmoon Pond State ...
4.9/5 Exceptional! (87 reviews)
Amazing Space
"This place can accommodate so many people. It's nice and remote on an absolutely beautiful lake. Contact with the owner through text made the check-in process incredibly easy. Would definitely stay again."

Reviewed on Nov. 22, 2021

Ultimate Relaxing Vacation
Brand New! Ski-in Sugarbush/Mount Ellen Cabin/Tiny House on 3.2 Acres

Brand New! Ski-in Sugarbush/Mount Ellen Cabin/Tiny House on 3.2 Acres

Waitsfield, VT
Located in the mountains, this Waitsfield cabin offers ski-in/ski-out access within 6 mi (10 km) of Mad River Glass Gallery, Sugarbush Ski Resort, and Mad River ...
5/5 Exceptional! (24 reviews)
Cozy and peaceful!
"Incredibly cozy and clean tiny home with all the amenities you could ask for! My husband enjoyed this kid free oasis for 2 nights, highly recommended!"

Reviewed on Nov. 15, 2021

Brand New! Ski-in Sugarbush/Mount Ellen Cabin/Tiny House on 3.2 Acres
Cozy Mountain Yurt on Organic Farm

Cozy Mountain Yurt on Organic Farm

Bristol, VT
Situated in the mountains, this romantic apartment building is 5.5 mi (8.8 km) from Cedar Lake and within 12 mi (20 km) of Halpin Covered Bridge and Lincoln ...
4.8/5 Exceptional! (4 reviews)
romantic, much needed getaway!
"What a sweet little spot! We walked the farm the last weekend of the summer, things were still in full bloom- flowers and veggies alike! It was a little bit of a drive to Burlington, but nice to be out of range of the city. We had more fun just hanging at the yurt than we expected, we could have ..."

Reviewed on Nov. 11, 2021

Cozy Mountain Yurt on Organic Farm
Lovely ski condo boasts great location, shared hot tub, pools, & tennis courts!

Lovely ski condo boasts great location, shared hot tub, pools, & tennis courts!

Warren, VT
The price is CA $128 per night from Dec 1 to Dec 1
Located in Warren, this family-friendly condo building is 0.7 mi (1.1 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery and Artisans' ...
4.5/5 Wonderful! (13 reviews)
Great place
"Place was great, just as advertised Only issue was we couldn’t find sheets for pull out bed, but figured out a solution. Very clean, beautiful area Will stay there again if back in area."

Reviewed on Nov. 8, 2021

Lovely ski condo boasts great location, shared hot tub, pools, & tennis courts!
 Authentic Log Cabin! & Hot Tub, Near Lake w/mountain Views-Campfires

Authentic Log Cabin! & Hot Tub, Near Lake w/mountain Views-Campfires

North Ferrisburgh, VT
This family-friendly North Ferrisburgh cabin is located on a lake, within 3 mi (5 km) of Rokeby Museum and Lake Champlain. Vergennes Falls Park and Mt. Philo ...
4.8/5 Exceptional! (84 reviews)
Relaxing Vermont getaway
"This is the second time we have come to this property. It is the perfect place to come for a relaxing Vermont getaway. The privacy of the property and beautiful views are an additional bonus."

Reviewed on Nov. 10, 2021

Authentic Log Cabin! & Hot Tub, Near Lake w/mountain Views-Campfires
Cozy condo w/3 shared pools, sauna, hot tubs, tennis - walk to Sugarbush Resort!

Cozy condo w/3 shared pools, sauna, hot tubs, tennis - walk to Sugarbush Resort!

Warren, VT
The price is CA $63 per night from Nov 30 to Nov 30
Located in Warren, this family-friendly condo building is 0.7 mi (1.1 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery and Artisans' ...
4.8/5 Exceptional! (19 reviews)
Perfect spot for 2!
"This property was so lovely and perfect for me and my partner. The check-in process was extremely easy, and everything was as expected in the unit. An amazing view off the back porch was great for morning coffee, the fire place was the perfect addition to curl up next to on the couch and read at ..."

Reviewed on Nov. 9, 2021

Cozy condo w/3 shared pools, sauna, hot tubs, tennis - walk to Sugarbush Resort!
Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ

Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ

Fair Haven, VT
This family-friendly Fair Haven cabin is located on the waterfront, 6 mi (9.7 km) from Lake Hortonia, and within 12 mi (20 km) of Halfmoon Pond State Park and ...
4.2/5 Very Good! (6 reviews)
Great time
"The property is a beautiful setting on a lake. Kayaks and dock area was great for the kids. Fire pit, grill and deck with a lot of seating available. However, the indoor and outdoor seating is very small scale and not comfortable for lounging. Additionally, the beds are set very low to the ground ..."

Reviewed on Sep. 13, 2021

Orwell Cabin on Sunrise Lake w/ Private Dock & BBQ
Mad River Valley Post and Beam 4 BR in Waitsfield Vt

Mad River Valley Post and Beam 4 BR in Waitsfield Vt

Waitsfield, VT
Situated in a rural location, this vacation home is within 6 mi (10 km) of Blueberry Lake Cross Country and Snowshoeing Center, Skinner Barn, and Ole's Cross ...
5/5 Exceptional! (28 reviews)
Great weekend getaway
"My wife and I had a wedding in the area. This was a perfect place to turn the wedding into a weekend getaway for our family."

Reviewed on Oct. 21, 2021

Mad River Valley Post and Beam 4 BR in Waitsfield Vt
Romantic Retreat:  10 acres, Hot Tub, Movie Theater

Romantic Retreat: 10 acres, Hot Tub, Movie Theater

Granville, VT
Located in the mountains, this family-friendly cabin is within 9 mi (15 km) of Cushman State Forest, Granville Gulf Reservation, and Texas Falls Recreation Area. ...
5/5 Exceptional! (268 reviews)
Girls Weekend Fun!
"My friends and I wanted a nice, relaxing weekend away from the boys and we got it! Everything was perfect. The Hot tub was AMAZING. Didnt need much communication with Jeff because he had everything labeled and clear directions for anything in the cabin but he was prompt to respond when we did talk ..."

Reviewed on Nov. 22, 2021

Romantic Retreat: 10 acres, Hot Tub, Movie Theater
Mountain condo with three shared pools, hot tub, tennis courts, game room, & gym

Mountain condo with three shared pools, hot tub, tennis courts, game room, & gym

Warren, VT
The price is CA $153 per night from Nov 30 to Nov 30
Located in Warren, this family-friendly condo building is 0.5 mi (0.8 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery and Artisans' ...
4.6/5 Wonderful! (7 reviews)
Clean and comfortable condo near Sugarbush mountain.
"Convenient location and comfortable accommodations. Kitchen could use some better pots & pans. We would book this condo again."

Reviewed on Apr. 7, 2021

Mountain condo with three shared pools, hot tub, tennis courts, game room, & gym
Inviting & secluded ski shuttle condo w/ a balcony - short hike to Mad River!

Inviting & secluded ski shuttle condo w/ a balcony - short hike to Mad River!

Warren, VT
The price is CA $96 per night from Nov 30 to Nov 30
Situated in Warren, this romantic condo building is 2.9 mi (4.6 km) from Sugarbush Ski Resort and 3 mi (4.8 km) from Ole's Cross Country Center. Blueberry Lake ...
4.7/5 Exceptional! (3 reviews)
Winter Ski Vacation
"Comfortable, well equipped and cozy home base for our ski week at Sugarbush ski resort, which is right down the road -- perfect location!"

Reviewed on Mar. 29, 2021

Inviting & secluded ski shuttle condo w/ a balcony - short hike to Mad River!
Moose lodge near Lake George

Moose lodge near Lake George

Ticonderoga, NY
This family-friendly Ticonderoga vacation home is located on a lake, within 3 mi (5 km) of Lake George, Star Trek: Original Series Set Tour and Ticonderoga Historical ...
4.7/5 Exceptional! (29 reviews)
Very comfortable, quiet neighborhood and friendly
"Relaxing atmosphere, accommodation excellent, would stay again."

Reviewed on Sep. 30, 2021

Moose lodge near Lake George
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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.

Other types of properties in Middlebury you may be interested in

Swift House Inn

Swift House Inn

3 out of 5
25 Stewart Ln, Middlebury, VT
The price is CA $229 per night from Dec 1 to Dec 1
Swift House Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Nov 29 to Nov 29
Courtyard Middlebury
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlebury. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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