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A Dutch County building with a covered walkway and red wagon wheels.

Photo by Ann Sair

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    Check prices for these dates, 12 – 13 December 2026

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    Our top choices for Middlebury holiday rentals

    1. Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

    A gravel path leading to a white house with a garage, surrounded by grassy fields and trees.

    2. | Hot Tub | Amish Farm Country | Pergola | Deck |

    A hot tub with a view of a grassy field and a cloudy sky.

    3. Farm Country Amish Country Newly Renovated

    A modern bathroom with a large mirror, a sink, and a towel rack.

    4. The Wellington Cottage

    A deck with a table and chairs, overlooking a lake with boats and a dock.

    5. The Back Porch Haven Stay in Amish Country yet close to Notre Dame

    A spacious living room with a high ceiling, exposed wooden beams, a brick wall, a staircase, and a large television.

    6. Hearthstone Hideaway #5 | Shewana Tiny Home Village

    A building with a number '5' on the front, a wooden facade, and a black roof.

    7. Lake Front Cottage Kayaks Game Table Fun

    A sunset view of a lake with boats docked at a pier.

    8. Sunset Oasis | Kayaks | Pedal Boat | Pier | Relax

    An outdoor patio with a table and chairs, a white fence, and a view of a lake.

    9. Millie's Cottage

    A house with a porch, a window with a flower box, and a chair outside.

    10. Relax and Unwind at the Cozy Cabin on Heaton Lake.

    A wooden deck with a hammock and a kayak, overlooking a lake with boats and a dock.

    11. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

    A covered porch with two chairs and a table, a brick wall, and string lights.

    12. Natural Nook | Tiny Home #2 in Amish Country!

    A small, single-story building with a dark roof and a welcoming entrance.

    13. Whispering Cottage #3 | Shewana Tiny Home Village

    A modern house with a dark exterior, a large front door, and a covered patio area with two wooden chairs and a small table.

    14. Arrowhead Riverfront! Beautiful, Peaceful, Private

    A two-story house with a balcony, surrounded by a well-maintained lawn and a body of water in the foreground.

    15. Little Luxe Retreat #7 | Tiny Home + Fire Table

    A house with a dark exterior, a front door, and a small patio area with two Adirondack chairs and a table.

    16. Serene Sanctuary | Tiny Home #1 in Amish Country!

    A modern building with a wooden facade, a covered entrance, and a clear sky.

    17. Designer Apartment-Walkable Downtown Goshen

    A residential building with a snow-covered porch and a sign for Shalma Interiors.

    18. The Gemini

    A pathway leading through a wooded area with a gated entrance.

    19. Riverhaven! Glamorous A-Frame on St Joe River!

    A riverside patio with outdoor seating, a fire pit, and a wooden deck overlooking the water.

    20. Simple Serenity Loft | Tiny Home #6 in Amish Country!

    A small, single-story building with a dark roof and wooden siding, featuring a front porch with two chairs and a small table.

    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.

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    Top Middlebury Hotel Reviews

    Farmstead Inn & Conference Center

    A porch with a gray bench and chair, a hanging fern, and a white column.

    Van Buren Hotel

    A covered patio with brick flooring, green cushioned seating, and a stone planter.

    Hotel Elkhart, Tapestry Collection by Hilton

    An outdoor seating area with tables and chairs, a building with a 'Hotel Elkhart' sign, and a 'Relish Cafe' across the street.

    Oakwood Resort

    A waterfront property with a large building featuring multiple levels and a dock extending into the water.

    Best Western Plus Howe Inn

    An indoor swimming pool with clear water, surrounded by wooden walls and large windows.

    Travelodge by Wyndham Elkhart

    A modern interior with a wooden staircase, a large open space, and multiple doors leading outside.

    Find out more about Middlebury

    Everything you need to know about Middlebury holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Middlebury holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Middlebury holiday rentals we have selected for you start as low as £47 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Middlebury rentals

    At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Are there holiday rentals in Middlebury?

    Yes, there are holiday rentals in Middlebury close to Deutsch Kase Haus, 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 shopping and gardens during your trip.

    What are some of the best holiday rentals that Middlebury has to offer?

    Millie's Cottage: This holiday home rental outside of Middlebury is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

    How many holiday rentals will I find in Middlebury?

    With 17 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlebury stay.

    What can I see and do in Middlebury?

    Stone Lake and Brokesha Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deutsch Kase Haus. While here, Meadow Valley Golf Club and Middlebury Public Library are other places worth a visit.

    What are holiday rentals like in Middlebury?

    Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlebury. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.