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Middlebury Vacation Rentals

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Vacation Rentals in Middlebury

Walk Everywhere in Middlebury

Walk Everywhere in Middlebury

60 Monroe Street, Middlebury, VT

Situated in Middlebury, this historic holiday home is within 1 mile (2 km) of Town Hall Theater and Middlebury College. Vermont Folklife Center and National ...

5/5Exceptional! (23 reviews)
Fabulous House

"This house was extremely comfortable with its open floor plan for our family of 7 who were in Middlebury for an intimate wedding. We are close to downtown and all the wedding events. The large deck and fire pit were an added bonus each evening. This property was perfect for us."…"

Reviewed on Sep. 27, 2020

Walk Everywhere in Middlebury
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 15-minute walk of National Museum of the Morgan Horse and Middlebury College. Town Hall ...

4.8/5Exceptional! (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!
Premier Ski in Ski out Mountainside Condo - Pet Friendly

Premier Ski in Ski out Mountainside Condo - Pet Friendly

205 Mountainside Drive, Warren, VT

Situated in Warren, this romantic condo is 0.3 mi (0.5 km) from Sugarbush Ski Resort and within 6 miles (10 km) of Blueberry Lake Cross Country and Snowshoeing ...

4.6/5Exceptional! (53 reviews)
Fall visit

"Info from owner provided super easy check-in to this conveniently located condo. Walking distance to several restaurants in the Village (recent pandemic has them functioning at limited or no hours, call first 🙄). Good for 3 adults...Clean, comfortable and allowed our older dog to join us on the ..."…"

Reviewed on Oct. 20, 2020

Premier Ski in Ski out Mountainside Condo - Pet Friendly
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Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!

Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!

202 Bridges Circle, Warren, VT

Located in Warren, this family-friendly condo is 0.6 mi (0.9 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery and Artisans' ...

4.8/5Exceptional! (5 reviews)
Sugarbush rental

"Overall a great property with tremendous views of the mountains. Pool was well-maintained. Buildings could use a paint job which I'm sure they have scheduled."…"

Reviewed on Jul. 26, 2019

Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

3.5 out of 5
2430 North Branch Road, Ripton, VT

Situated in Ripton, this cabin is within 9 miles (15 km) of Robert Frost Wayside Trail, Green Mountain National Forest and Rikert Nordic Center. Middlebury College ...

5/5Exceptional! (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
Ultimate Relaxing Vacation

Ultimate Relaxing Vacation

1900 Perch Pond Rd, Fair Haven, VT

Situated on the waterfront, this historic cabin is within 12 miles (20 km) of Lake Hortonia, Mount Independence State Historic Site and Halfmoon Pond State Park. ...

4.9/5Exceptional! (55 reviews)
Amazing cabin

"Even more than we expected for the price. Amazing property. Everything we needed was provided"…"

Reviewed on Nov. 23, 2020

Ultimate Relaxing Vacation
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 in the mountains, within 3 mi (5 km) of Rokeby Museum and Lake Champlain. Thompsons Point is 3 mi (4.8 ...

4.8/5Exceptional! (55 reviews)
Gorgeous, warm, fun... Perfect

"The home is lovely, a modern log cabin on the edge of a giant field with grand mountain views. It's also a ton of fun - games galore, a big hot tub with a great view and plenty of space for sitting and chatting. The best part is definitely the sunset over the mountains from the hot tub. Hope to come ..."…"

Reviewed on Nov. 3, 2020

Authentic Log Cabin! & Hot Tub, Near Lake W/mountain Views-campfires
Kamp Koby - Lake Front Camp on Lake Hortonia

Kamp Koby - Lake Front Camp on Lake Hortonia

96 Lhcs Rd, Fair Haven, VT

Situated on the waterfront, this historic cabin is 0.1 mi (0.1 km) from Lake Hortonia and within 6 miles (10 km) of Halfmoon Pond State Park and Beebe Pond. ...

2/5 (2 reviews)
Awful Atrocious Disgusting Hideous Grossly over priced

"We are not sure if we saw Rat hair or cat hair. A shower with a stream weaker than your garden hose. Tiny cramped bed so small you better be under 5'5 in that bed, No privacy curtains, right out of the shower you have to try and dry off in the bedroom. The refrigerator is loud enough to wake up everyone ..."…"

Reviewed on Sep. 11, 2019

Kamp Koby - Lake Front Camp on Lake Hortonia
NOW Open !! Sugarbush SKI IN OUT Remodled 1963 Trailside SKI Chalet Free Wifi

NOW Open !! Sugarbush SKI IN OUT Remodled 1963 Trailside SKI Chalet Free Wifi

122 East Road, Warren, VT
The price is CA $318 per night from Dec 3 to Dec 4

This family-friendly Warren chalet is located on the riverfront, 1 mi (1.6 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery ...

4.8/5Exceptional! (81 reviews)
Perfect weekend

"Just the perfect spot for a long Columbus Day weekend. Can’t beat the foliage and it’s less than an hour to Burlington or Stowe. The house was very clean and the owner was very helpful before we checked in with recommendations and information about the area."…"

Reviewed on Oct. 13, 2020

NOW Open !! Sugarbush SKI IN OUT Remodled 1963 Trailside SKI Chalet Free Wifi
Stetson Hollow Cabin By Stetson Brook

Stetson Hollow Cabin By Stetson Brook

23 Stetson Hollow, Warren, VT
The price is CA $325 per night from Dec 1 to Dec 2

Situated in Warren, this romantic cabin is within 6 miles (10 km) of Ole's Cross Country Center, Sugarbush Ski Resort and Granville Gulf Reservation. Blueberry ...

4.7/5Exceptional! (34 reviews)
Family time

"We enjoyed our weekend getaway to just spend time together - puzzles and games. And the walk in the woods right from the cabin was exactly what we were looking for. Jill was very kind with treats and helpful suggestions. Can’t wait for our next cabin getaway!"…"

Reviewed on Nov. 25, 2020

Stetson Hollow Cabin By Stetson Brook
Incredible Family Getaway Home With Boat Dock

Incredible Family Getaway Home With Boat Dock

55 Sagamore Drive, Ticonderoga, NY

Situated on the waterfront, this holiday home is within 3 miles (5 km) of Ticonderoga Historical Society, Star Trek: Original Series Set Tour and Ticonderoga ...

5/5Exceptional! (43 reviews)
Relaxing Lake Getaway

"If you’re looking for a quiet, relaxing lake getaway, this is your spot! My family and I needed to get out of town and we came upon this little gem. We were met by Shauna, the housekeeper, while checking in. The house was spotless, and very well maintained. She was able to direct us to a local grocer ..."…"

Reviewed on Oct. 25, 2020

Incredible Family Getaway Home With Boat Dock
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

267 High Rd, Waitsfield, VT

Situated in Waitsfield, this romantic cabin is within 6 miles (10 km) of Mad River Glass Gallery, Sugarbush Ski Resort and Mad River Glen Cooperative. Artisans' ...

5/5Exceptional! (15 reviews)
Tiny House in Fayston

"Amazing stay! Mike was super kind and very helpful. House is beautiful and immaculately maintained. The surrounding area has scenery you can't beat. Overall an amazing time!"…"

Reviewed on Oct. 21, 2020

Brand New! Ski-in Sugarbush/mount Ellen Cabin/tiny House on 3.2 Acres
14 Snowside 2 Bedroom Condo

14 Snowside 2 Bedroom Condo

3.5 out of 5
14 Snowside, Unit 14, Waitsfield, VT

Situated in Waitsfield, this golf condo is within 6 miles (10 km) of Mad River Glass Gallery, Sugarbush Ski Resort and Mad River Glen Cooperative. Artisans' ...

14 Snowside 2 Bedroom Condo
Immaculate Mountain Cabin With Sunrise and Mountain Views

Immaculate Mountain Cabin With Sunrise and Mountain Views

2430 North Branch Rd, Ripton, VT

Set in Ripton, this family-friendly cabin is within 9 mi (15 km) of Robert Frost Wayside Trail, Rikert Nordic Center and Middlebury College Snow Bowl Ski Area. ...

Immaculate Mountain Cabin With Sunrise and Mountain Views
Orwell Cabin on Sunrise Lake W/pvt Dock & BBQ

Orwell Cabin on Sunrise Lake W/pvt Dock & BBQ

205 Sunrise Lake Road, Fair Haven, VT

Situated on the waterfront, this cabin is within 12 miles (20 km) of Lake Hortonia, Halfmoon Pond State Park and Half Moon State Park. Bomoseen State Park and ...

4.3/5Excellent! (4 reviews)
Excellent location

"Great place to relax. Private lake. Really had a great time at this property. House looks even better in person. Me and my family enjoyed our stay."…"

Reviewed on Sep. 8, 2020

Orwell Cabin on Sunrise Lake W/pvt Dock & BBQ
Moose Lodge Near Lake George

Moose Lodge Near Lake George

27cottage road, Ticonderoga, NY

Located in North Lake George, this holiday home is within 3 miles (5 km) of Ticonderoga Historical Society, Star Trek: Original Series Set Tour and Ticonderoga ...

4.7/5Exceptional! (20 reviews)
Great Location!

"Everything was great! The house was just as described and we had no issues. We had a great weekend hiking and loved the proximity to the lake."…"

Reviewed on Oct. 12, 2020

Moose Lodge Near Lake George
Unique Luxury Church Near Killington! Sleeps 10! Amazing Great Room!

Unique Luxury Church Near Killington! Sleeps 10! Amazing Great Room!

3325 US Rte 7, Pittsford, VT

Situated in Pittsford, this holiday home is 1.3 mi (2 km) from New England Maple Museum and 1.9 mi (3.1 km) from Proctor-Pittsford Country Club. Dorset Quarry ...

5/5Exceptional! (2 reviews)
Great place!

"We really enjoyed our stay and loved staying in the church! It was so spacious and comfortable. I hope we can go back again someday!"…"

Reviewed on Aug. 28, 2020

Unique Luxury Church Near Killington! Sleeps 10! Amazing Great Room!
Romantic Retreat: 10 Acres, Hot Tub, Movie Theater

Romantic Retreat: 10 Acres, Hot Tub, Movie Theater

1718 Butz Rd, Granville, VT

Situated in the mountains, this romantic cabin is within 9 miles (15 km) of Cushman State Forest, Granville Gulf Reservation and Texas Falls Recreation Area. ...

5/5Exceptional! (202 reviews)
Lovely spot for a getaway!

"My family of four needed a getaway and we found the perfect spot in Jeff’s cabin! It’s beautifully designed, comfortable and fun. Our two kids ages 7 and 10 loved every minute including the outside tetherball and the nightly movies projected on the large screen. The small sleeping loft, the window ..."…"

Reviewed on Nov. 28, 2020

Romantic Retreat: 10 Acres, Hot Tub, Movie Theater
Cozy Cabin With Firepit and Screened Porch

Cozy Cabin With Firepit and Screened Porch

2430 North Branch Rd, Ripton, VT

Set in Ripton, this family-friendly cabin is within 9 mi (15 km) of Robert Frost Wayside Trail, Rikert Nordic Center and Middlebury College Snow Bowl Ski Area. ...

5/5Exceptional! (1 review)
Romantic Bliss on the Mountain

"We loved our stay in this lovely peaceful Cabin #6! We loved the comfy bed, the hot tub, privacy, everything we needed was in our cabin!!! The screened in porch is such a perfect addition, no bugs to worry. So glad we were able find you on VRBO.. Thank you so much for offering your home as a vacation ..."…"

Reviewed on Jul. 20, 2019

Cozy Cabin With Firepit and Screened Porch
Inviting Timber Frame Cabin in Vermont's Green Mountains

Inviting Timber Frame Cabin in Vermont's Green Mountains

2430 North Branch Rd, Ripton, VT

Set in Ripton, this family-friendly cabin is within 9 mi (15 km) of Robert Frost Wayside Trail, Rikert Nordic Center and Middlebury College Snow Bowl Ski Area. ...

Inviting Timber Frame Cabin in Vermont's Green Mountains
Don't see what you're looking for?
See all available properties in Middlebury
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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.

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.

Frequently asked questions

Are there vacation rentals in Middlebury?
Yes, we offer vacation rentals close to the most popular attractions in Middlebury, or you can go with a more remote option if you want a relaxing place to stay. Our travelers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.
What are some of the best vacation home rentals that Middlebury has to offer?
Walk Everywhere in Middlebury: This highly rated vacation home rental in Middlebury offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.
How many vacation rentals are there in Middlebury?
Expedia has 7 vacation rentals for your stay in Middlebury.
What’s there to see and do in Middlebury?
Cultural attractions to visit include Town Hall Theater and National Museum of the Morgan Horse. In the larger area, you’ll find popular places like Sugarbush Ski Resort and Green Mountain National Forest.
What’s a vacation rental in Middlebury like?
Vacation rentals are private properties you can stay in for a couple of days or more in Middlebury. Vacation rentals feature amenities like WiFi and washers and dryers so you’ll have everything you need. If you’re concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You’ll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.

Other types of properties in Middlebury you may be interested in

Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Free cancellationReserve now, pay when you stay
The price is CA $144 per night from Dec 20 to Dec 21
Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
25 Stewart Ln, Middlebury, VT
Free cancellation
The price is CA $181 per night from Dec 20 to Dec 21
Swift House Inn
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.