Search Holiday Rentals in Middlebury

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Middlebury

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is £479
includes taxes & fees
8 Jul - 9 Jul
Korean Gourmet Stay at Swiss Farm Inn - 1 night

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is £611
includes taxes & fees
10 Jul - 11 Jul
Serene Architect-designed Vermont Chalet 4 Bedroom Home

Secluded Mountain Getaway with Hot tub and Views!

The price is £453
includes taxes & fees
8 Jul - 9 Jul
Secluded Mountain Getaway with Hot tub and Views!

Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views

10.0 out of 10, Exceptional, (8)
"Beautiful home, large inviting rooms. The views are gorgeous. "
Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views

Beautiful Country Home with Hot Tub & Pool Table

10.0 out of 10, Exceptional, (1)
"It was really lovely. Very comfortable, easy to keep clean. Everyone loved the hot tub."
The price is £585
includes taxes & fees
20 Jul - 21 Jul
Beautiful Country Home with Hot Tub & Pool Table

Mad Mountain Meadows - Stunning Mountain Views!

The price is £486
includes taxes & fees
15 Jul - 16 Jul
Mad Mountain Meadows - Stunning Mountain Views!

Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

10.0 out of 10, Exceptional, (12)
"We had a wonderful time and the place was great. We found everything we needed easily and loved the charm of the place. Perfect spot for a ski vacation just a few min from sugarbush and mad river."
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

Top of the Hill Modern Retreat

9.6 out of 10, Exceptional, (5)
"All super but it needs more cozy, sheepskin rugs because of the cement floor. Maybe offer slippers too. "
The price is £488
includes taxes & fees
23 Jul - 24 Jul
Top of the Hill Modern Retreat

Entire Enchanting, Light-Filled 1830 Farmhouse

9.8 out of 10, Exceptional, (9)
"We came up to Vermont for a wedding and the "farm house" was just what we needed. Thank you! Much appreciated the easy check in and allowing us to arrive a bit earlier to get ready for the wedding bash. P. Murray"
The price is £481
includes taxes & fees
8 Jul - 9 Jul
Entire Enchanting, Light-Filled 1830 Farmhouse

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (37)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

10.0 out of 10, Exceptional, (4)
"Good area"
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (19)
"We enjoyed our stay here. The property was 10 minutes from the Sugarbush resort, making it easy to catch the first lift of the day. It's also about a 5-minute drive from the historic Warran Village, which is worth walking around for a bit. Checking in and checking out was super easy. I would recommend to anyone looking for a no-frills stay that is super close to the mountain! "
Beautiful home located in the Mad River Valley

Beautiful Home with views and a hot tub 10 minutes from Sugarbush Resort

10.0 out of 10, Exceptional, (14)
"We loved the house and the location. Would definitely stay again."
Beautiful Home with views and a hot tub 10 minutes from Sugarbush Resort

Large Vermont ski home on private scenic lot centrally located in the Mad River Valley

10.0 out of 10, Exceptional, (14)
"Wonderful ski house close to the mountain and a great house layout for young children / families!"
Large Vermont ski home on private scenic lot centrally located in the Mad River Valley

Ski, Hike & Relax. Warm 1BR Spot.

The price is £101
includes taxes & fees
8 Jul - 9 Jul
Ski, Hike & Relax. Warm 1BR Spot.

Stunning Modern Retreat Overlooking The Mad River

10.0 out of 10, Exceptional, (9)
"Great location! House was very nice and spacious. Definitely would book again! "
The price is £541
includes taxes & fees
30 Jul - 31 Jul
Stunning Modern Retreat Overlooking The Mad River

Ridge House - Modern Log Home Nestled on top of a Private Mountain

10.0 out of 10, Exceptional, (13)
"Great property, would rent again in the future! "
Ridge House - Modern Log Home Nestled on top of a Private Mountain

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (37)
"A perfect location for family weekend at Norwich University! We fit a family of 7 and all slept comfortably, lounged in the living room, or gathered in the spacious kitchen where I cooked and baked all weekend. We will definitely stay again!"
Classic Vermont Farmhouse near Sugarbush Resort

Beautiful Farmhouse Close to Warren Village and Sugarbush Resort

10.0 out of 10, Exceptional, (10)
"Very nice place. Thank you"
Beautiful Farmhouse Close to Warren Village and Sugarbush Resort
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Danforth Pewter, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middlebury has to offer?

Beautiful 4-Bedroom Home beside Middlebury College: This highly rated holiday home rental in Middlebury is located near skiing, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Middlebury?

Expedia has 13 holiday rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include National Museum of the Morgan Horse and Town Hall Theater, whereas Green Mountain National Forest and Middlebury Dog Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Pulp Mill Covered Bridge and Otter Creek Brewing.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.