Holiday Homes in Middlebury

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Middlebury

Fridge, microwave, oven, stovetop
Gorgeous home with amazing lake views, fireplace, firepit, hot tub, & balcony
10.0 out of 10, Exceptional, (2)
Gorgeous home with amazing lake views, fireplace, firepit, hot tub, & balcony
Property grounds
Lake Bomoseen Luxury Waterfront, Family Friendly Getaway!
10.0 out of 10, Exceptional, (8)
"We came as a family to visit with family in the area. The home was very well maintained and clean. All appliances, bedding and towels were great quality. The house was spacious and had plenty of room to spread out. The location was great with an amazing view. Would highly recommend."
Lake Bomoseen Luxury Waterfront, Family Friendly Getaway!
Pool
Private 5BR home, pool, new hot tub, mt views, & fireplace!
10.0 out of 10, Exceptional, (39)
"We loved it! Great location, close to the quaint town of Waitsfield. If you’re lucky with the weather and you have kids- amazing sledding hill! (We did insist the kids wear their ski helmets as it was long and FAST). Kitchen well supplied. The hosts were always helpful and responsive."
Private 5BR home, pool, new hot tub, mt views, & fireplace!
Save an average of 15% on thousands of hotels when you're signed in
Interior
The Groovy Lake House
10.0 out of 10, Exceptional, (1)
"We had a large-ish group for my son's graduation from Middlebury College and could not have asked for a nicer host or place. The upstairs/main floor is really so much cooler even than the photos portray. You feel like you are out in the field with huge windows in every room. The basement is dark and cool and very flexible bed and roomwise. Everyone felt very comfortable and well cared for. Kara is a fantastic and responsive host and we are so grateful for the soft landing."
The Groovy Lake House
Fridge, microwave, oven, stovetop
Remodeled Barn in Champlain Valley, Essex, NY
10.0 out of 10, Exceptional, (40)
"Always a great stay!"
Remodeled Barn in Champlain Valley, Essex, NY
Sun-loungers, beach towels
Lake George Waterfront with Dock Space, fire pit and game room!
10.0 out of 10, Exceptional, (12)
"We had a great time at this property. We loved the location, had a great time in the game room and were overall thrilled w our vacation. We had everything we needed to cook at home and we slept great on the comfy mattresses. We could not get the fireplace to work, but that had no impact on our stay. Thank you!"
Lake George Waterfront with Dock Space, fire pit and game room!
Fridge, microwave, oven, stovetop
Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
10.0 out of 10, Exceptional, (2)
"Very nice stay, a couple of minor settling in issues such as one toilet not working but this was sorted out quickly. A minor point was that there were no curtains anywhere in the house. Not bothered about people seeing in as the property is not overlooked but meant we woke up when the sun came up."
Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
Fridge, microwave, oven, stovetop
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
10.0 out of 10, Exceptional, (46)
"The house is par excellence.....the host is amazing. Brandon is a beautiful town....with beautiful people....and food!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Fridge, microwave, oven, stovetop
Stunning Modern Retreat in Warren Village
10.0 out of 10, Exceptional, (2)
"This is an amazing home. You will be immersed in the surroundings both in and outside the home. The entire house is a work of art, not to mention the actual art in the home. The ideas and execution of how this house was done is just excellent. A+"
The price is AU$1,297
per night
18 June - 19 June
Stunning Modern Retreat in Warren Village
Smart TV, fireplace, offices
Secluded Vermont Home with Stunning Private View! Prime Location!
10.0 out of 10, Exceptional, (9)
"Perfect spot for a bunch of couples to use as a base for skiing Sugarbush. Lawsons a 5 minute drive. Excellent stock of board games. Kitchen is well stocked for cooking (bring your own spices). Rental management company is really responsive. Definitely be prepared for a tough Vermont dirt road up to the house when it is mud season!"
Secluded Vermont Home with Stunning Private View! Prime Location!
Sugarbush Resort; Spectacular Town Home! Discounts available at the Après Chalet
9.8 out of 10, Exceptional, (33)
"Location and amenities were great. Hope to book again for the next class reunion."
Sugarbush Resort; Spectacular Town Home! Discounts available at the Après Chalet
Property grounds
Ski home in the woods with a private hot tub & mountain views
9.8 out of 10, Exceptional, (34)
"Super stay, really cool house, fantastic kitchen and big hot tub. Highly recommended"
Ski home in the woods with a private hot tub & mountain views
Property grounds
Beautiful home located in the Mad River Valley
9.8 out of 10, Exceptional, (31)
"We had a nice stay. The house was clean and had everything we needed. Easy drive to Sugarbush and Mt Ellen."
Beautiful home located in the Mad River Valley
Property grounds
Beautiful 4-Bedroom Home beside Middlebury College
9.6 out of 10, Exceptional, (29)
"We were adult family members in town to visit our mother. Really comfortable house with a lot of space. Centrally located. Would highly recommend."
Beautiful 4-Bedroom Home beside Middlebury College
A heated pool
Contemporary home with pool and tennis court, 3 mins from Sugarbush
9.6 out of 10, Exceptional, (4)
"Good setting for a large family group. Beautiful views. The mountain and weather were good."
Contemporary home with pool and tennis court, 3 mins from Sugarbush
Property grounds
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK
9.6 out of 10, Exceptional, (30)
"We had a great time in this clean, beautiful home!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK
Fridge, microwave, oven, stovetop
Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer
9.6 out of 10, Exceptional, (26)
"Absolutely perfect for our early 20s children on a ski weekend with us. Proximity to Mad River Glen cannot be beat. Great set up with bedrooms and kitchen is perfect and we loved the great room set up."
Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer
Beach
Cozy Cottage Overlooking Lake Champlain
9.6 out of 10, Exceptional, (15)
"What a wonderful place. The cottage ‘Margot’ was a great place to call home during our visit to Westport. The pictures of this place convey an accurate image. Margot is the my definition of a rustic cottage on the lake. The cottage has simple but efficient furnishings and well functioning infrastructure. The shower had great water pressure and plenty of hot water. Though we didn’t cook, the kitchen has all the necessities. We made good use of the refrigerator and the laundry. The Wi-Fi worked...
Cozy Cottage Overlooking Lake Champlain
Property grounds
Beautiful lake house on Lake Champlain!
9.6 out of 10, Exceptional, (78)
"We very much enjoyed our five-day stay at this house on Lake Champlain -- at one of the narrowest parts of the lake (NY is a kayak away). There's a high-ceiling living room, well-stocked kitchen, comfortable beds, and it's a great area for runs/biking/walks. We very much recommend it."
Beautiful lake house on Lake Champlain!
On the beach, sun-loungers
Lakefront Isolated Bliss
9.4 out of 10, Exceptional, (93)
"Lovely home that has everything you need , located on a very secluded street . you can feel that this home is loved : has lots of great books and beautiful paintings ( home is owned by the artist ) Very cozy with a lot of character and overlooking Lake Champlain . Beautiful terrace . Local stores sell very good produce from nearby farms its organic and very tasty . great hiking at the Green Mountains for people who like forest ; trails are empty ( but about an hour away by car) Or you can walk...
Lakefront Isolated Bliss
Don't see what you're looking for?
See all available properties in 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.

Other property types in Middlebury

Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ultimate relaxing vacation
9.8 out of 10, Exceptional, (152)
"Very quiet, very spacious, huge outside deck. "
The price is AU$265
per night
23 May - 24 May
Ultimate relaxing vacation
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.

Middlebury Holiday Homes information

Number of reviews
322
Accommodation
220 Holiday Homes
Lowest Price
Highest Price

Recent Reviews in Middlebury
Expedia verified reviews