Search Cottages 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

Compare 50 Cottages in Middlebury with updated reviews, rates, and availability.

Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

8.6 out of 10, Excellent, (11)
"Nice waterfront location "
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Camp Roosevelt on Lake Champlain

2.0 star property
Camp Roosevelt on Lake Champlain

A cottage in the mountains minutes from skiing & hiking

9.0 out of 10, Wonderful, (6)
"Wife and I will probably book this amazing little cottage for all trips to Vermont. Cottage in country with Amazing Views, that’s what my wife and I wanted, and we couldn’t have imagined finding a better place."
A cottage in the mountains minutes from skiing & hiking

Dog-friendly cottage on acreage with nearby creek & wood stove

9.0 out of 10, Wonderful, (55)
"The house was cute, and the location was good. We liked the woods and stream around the house and the quiet road it was on. The views of the woods out the windows were lovely. There were a few old board games for the kids, but not much else for them to do when it was raining. The TV worked well, and we had internet. The bed downstairs was a little hard and the sheets looked old. Some of the furniture was obviously old, but we didn't use a lot of it anyway. The kids stayed in the loft and...
Dog-friendly cottage on acreage with nearby creek & wood stove

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (48)
"Our stay at Camp Tiger Ted was so wonderful. The amount of detail and care David put into building and now maintaining the property is second to none. The house was meticulously clean and had so many charming details. David also gave us both massages in his in home studio which waA the most relaxing way to end our stay!"
The price is SAR 469
SAR 736 total
includes taxes & fees
1 Dec - 2 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Rustic Lakeside Camp in Essex, NY on Lake Champlain

9.6 out of 10, Exceptional, (42)
"The property is in a prime location on Lake Champlain. We brought our own kayaks and access to the lake was easy. The house was stocked with everything we would need and the hosts were very attentive. Helpful Info was provided on activities and shopping in the area. One suggestion for future guests is to bring reading lights, since lighting in common areas was rather dim. "
Rustic Lakeside Camp in Essex, NY on Lake Champlain

Cozy Cottage on Beautiful Lake Champlain.

9.6 out of 10, Exceptional, (167)
"Place is simple and clean, could benefit from a comfy couch in the living area opposite the TV for more comfortable lounging. We really enjoyed the location--right on beautiful Lake Champlain. Host was very accommodating. We recommend this cozy little cottage."
Cozy Cottage on Beautiful Lake Champlain.

Cozy Lake Champlain Cottage w/ Beautiful View

9.6 out of 10, Exceptional, (24)
"We enjoyed our stay very much!! especially the views of the fall foliage on the mountains across the lake!!! everything was nice and clean and very convenient!! Firewood was also provided!!!"
Cozy Lake Champlain Cottage w/ Beautiful View

Dog-Friendly Lakefront cabin w/Free WiFi, Patio, Deck, Dock, & Water Views

5.8 out of 10, (6)
"If you are good with an authentic rustic environment- complete with small rodent catch and release trap under the stairs, a little water coming in the bedroom ceiling when it rains, bugs galore, and supplying your own drinking water— then OK. Everyone else consider yourselves forewarned. There has been absolutely no maintenance done on this property in decades. The local staff are wonderful."
Dog-Friendly Lakefront cabin w/Free WiFi, Patio, Deck, Dock, & Water Views

Warren Vacation Rental ~ 3 Mi to Sugarbush Resort!

9.8 out of 10, Exceptional, (7)
"My wife and I really enjoyed our stay. The home was lovingly restored and attention to detail was evident both in the house and the grounds. The stonework and outdoor spaces are spectacular."
Warren Vacation Rental ~ 3 Mi to Sugarbush Resort!

Quaint Cottage On The Lake! CURRENTLY RENOVATING!!

9.2 out of 10, Wonderful, (24)
"Relaxed by the lake, paddle board, visit family"
Quaint Cottage On The Lake! CURRENTLY RENOVATING!!

Quaint 2 Bedroom Cottage on Lake George

9.6 out of 10, Exceptional, (9)
"Good experience. We enjoyed the beach and playground. Cottage is described accurately in the listing. "
Quaint 2 Bedroom Cottage on Lake George

Lake Champlain Charming Cottage

Lake Champlain Charming Cottage

4 Bedroom, 1.5 bath- Air-Conditioned House on Lake Champlain - Seasonal May- Oct

10.0 out of 10, Exceptional, (14)
"The view of the lake is gorgeous, and the house felt like a home in every way. The beds were comfortable and the living room spacious. It was a great setting to visit with our family. "
4 Bedroom, 1.5 bath- Air-Conditioned House on Lake Champlain - Seasonal May- Oct

Classic lakefront cabin with screened-in porch & great views - dogs welcome

9.4 out of 10, Exceptional, (8)
"The property itself, along with the staff were fantastic! The island has great trails, and our dog had a blast. Getting to and from the island is pretty smooth - ferry drivers were usually ready in a couple minutes time. Couple things to note - the check-in information we received was a little sparse relative to other stays via VRBO. If you're used to getting an access code, you won't for this property. And teh driving directions, while good once you've got your bearings, are not great for...
Classic lakefront cabin with screened-in porch & great views - dogs welcome

Ski Lodge Mtn Retreat w/ Fire Pit, Deck & Views!

3.0 star property
Ski Lodge Mtn Retreat w/ Fire Pit, Deck & Views!

Hague Vacation Rental ~ 2 Mi to Lake George!

2.0 star property
6.0 out of 10, (1)
"Place was great but owner should state upfront that there is no WIFI and NO cell service. Kind of needed the WiFi to plan out my vacation plans and not having ANY cell service whatsoever made that impossible. Place was In Great shape , VERY private , driveway was extremely steep making towing my trailer up it a little sketchy. But other than those two issues place was great! "
Hague Vacation Rental ~ 2 Mi to Lake George!

Dog-friendly retreat with porch, kayaks, & amazing views - right on the water

8.6 out of 10, Excellent, (7)
"We were very excited to arrive at this beautiful location, however, the listing doesn't accurately describe this rental. Be aware that the windows don't close properly (or at all), there is a lot of noise during the night, properly critters. This unit is above someone and the neighbors are quite close. Very nice ferry driver! If you are into a glamping experience, it is worth it, but the price should reflect this."
Dog-friendly retreat with porch, kayaks, & amazing views - right on the water

Dog-friendly bay-front cabin with screened porch & great views - next to trails

9.4 out of 10, Exceptional, (9)
"An incredible Lakeside cottage, easy access to the water, boats to play with and very very friendly staff"
Dog-friendly bay-front cabin with screened porch & great views - next to trails

Charming Waitsfield Escape: 10 Mi to Sugarbush!

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Waitsfield Escape: 10 Mi to Sugarbush!
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.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlebury

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (41)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
Cozy Loft for two with Hot Tub
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.

Frequently asked questions

Why book your cottage in Middlebury with Expedia?
Booking a cottage in Middlebury is as simple as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From chic retreats to low-cost stays and cottages that have perks like free WiFi, Expedia has something for all styles. As for epic deals? We’ve got them too!
How can I find cheap cottages in Middlebury?
A great way to locate cheap cottages in Middlebury is with Expedia’s handy filter tool. Narrow down your search results by amenities, star rating and budget to land unbeatable bargains in a couple of clicks.