Best Vacation Homes in Middlebury
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $465/Night
For 7 Nights US $3,254
243.53 ft²
18 Guests
8 Bedrooms
8 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
US $266/Night
For 7 Nights US $1,860
1500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $422/Night
For 7 Nights US $2,952
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $786/Night
For 7 Nights US $5,504
180.3 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Bed & Breakfast
- Balcony/Terrace
- Breakfast
- Parking
US $175/Night
For 7 Nights US $1,225
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $181/Night
For 7 Nights US $1,269
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $357/Night
For 7 Nights US $2,497
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $171/Night
For 7 Nights US $1,200
Middlebury Luxury Rentals
3500 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,323/Night
For 7 Nights US $9,258
13 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,198/Night
For 7 Nights US $8,389
2000 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $780/Night
For 7 Nights US $5,457
5000 ft²
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $758/Night
For 7 Nights US $5,305
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $736/Night
For 7 Nights US $5,150
2101 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $522/Night
For 7 Nights US $3,653
US $519/Night
For 7 Nights US $3,633
3000 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $515/Night
For 7 Nights US $3,606
Middlebury Pet Friendly Vacation Rentals
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $345/Night
For 7 Nights US $2,413
US $173/Night
For 7 Nights US $1,212
7 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $313/Night
For 7 Nights US $2,189
220.66 ft²
2 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
US $172/Night
For 7 Nights US $1,206
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $638/Night
For 7 Nights US $4,469
2700 ft²
7 Guests
4 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $551/Night
For 7 Nights US $3,857
11 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $2,240/Night
For 7 Nights US $15,680
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Air Conditioner
- Child Friendly
US $156/Night
For 7 Nights US $1,092
Middlebury Large Vacation Homes
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Kitchen
- Parking
US $443/Night
For 7 Nights US $3,100
Why Choose Rent By Owner for your Middlebury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middlebury
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this charming destination can enhance your experience, as seasonal changes in the area offer unique opportunities for relaxation and exploration throughout the year.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences lively outdoor activities and a vibrant atmosphere, making it an ideal time to enjoy your stay in the region.
Average Temperature Daytime: Approximately 75-85°F - Nighttime: About 55-65°F
Fall (September to November)
Autumn brings stunning foliage and crisp air, attracting visitors seeking picturesque views and outdoor exploration in this area.
Average Temperature Daytime: Around 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Late Winter (January to February)
The quieter winter months offer a peaceful retreat with fewer crowds, perfect for those looking to experience the region’s serene beauty.
Average Temperature Daytime: Approximately 20-30°F - Nighttime: 10-20°F
Early Spring (March to April)
As the region transitions from winter, early spring provides a subtle awakening with fewer travelers and blooming natural scenery.
Average Temperature Daytime: Around 40-55°F - Nighttime: 25-35°F
Weekly Weather Forecast for Middlebury
How to Book Your Middlebury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlebury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck for relaxing and dining outdoors amidst scenic views.
- Take advantage of private gardens or landscaped yards perfect for leisurely strolls or picnics.
- Make the most of outdoor grilling facilities to cook up local flavors during your stay.
- Explore nearby hiking trails or nature paths accessible directly from the property.
- Benefit from access to outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
- Utilize outdoor recreational equipment such as bikes, kayaks, or paddleboards available for guest use.
- Relax in a private outdoor hot tub or spa, offering a soothing retreat after outdoor adventures.
Top Attractions Around Middlebury
What attractions are nearby?
Within this charming region, you can explore a variety of outdoor activities such as hiking, skiing, and scenic drives, ensuring an engaging experience just moments from your vacation rental in Middlebury.
Family Activities
- Middlebury College Museum of Art: Explore engaging exhibitions and family-friendly programs that make art accessible and enjoyable for visitors of all ages.
- Otter Creek Path: Enjoy scenic walks or bike rides along this peaceful trail, perfect for outdoor family adventures in the region.
- MiddSummer Festival: Experience lively local events throughout the summer, offering entertainment and activities suitable for children and adults alike.
- Boyden Valley Winery & Distillery: Participate in family-friendly tours and tastings that introduce you to the area's unique regional flavors in a welcoming setting.
Adult Activities
- Explore the Middlebury College Campus: Discover historic architecture and vibrant cultural events at this renowned liberal arts college, a hub of activity in the area.
- Visit the Middlebury Farmers' Market: Enjoy browsing local produce, artisanal goods, and handcrafted items, perfect for experiencing the region's community spirit.
- Tour the Lake Champlain Maritime Museum: Dive into regional maritime history with engaging exhibits and boat tours that highlight the area's rich waterways.
- Embark on a Scenic Drive along the Vermont Byways: Experience breathtaking views of rolling hills and lush landscapes as you explore scenic routes around here.
Other Places to Stay in Middlebury, VT
Middlebury - Warren
Addison County
Halpin Covered Bridge
Cornwall
Middlebury College
Kevin P. Mahaney '84 Center for the Arts
Porter Medical Center
UVM Health Network - Porter Medical Center
Porter Hospital
Holy Cow Inc.
National Museum of the Morgan Horse
Town Hall Theater
Middlebury Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take advantage of the region's farm-to-table restaurants and cozy cafés to enjoy authentic Vermont flavors during your stay.
- Visit Seasonal Events: Check out the local calendar for seasonal festivals and outdoor activities that showcase the area's vibrant community spirit.
- Discover Scenic Outdoors: Make time to hike or bike through nearby trails and parks, immersing yourself in the natural beauty that makes this destination unique.
- Choose a Prime Location: Select vacation rentals in convenient areas to easily access the region’s cultural sites, outdoor adventures, and local shops for a well-rounded experience.
Transportation Options
- Middlebury Transit Services: This local bus service provides convenient transportation within the area, making it easy to explore without a car.
- Amtrak Train Station: The nearby train station offers reliable rail connections for travelers wishing to access the region by train.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are available for flexible, door-to-door travel around Middlebury and beyond.
- Car Rentals: Several rental agencies operate in the area, allowing you to explore Vermont's scenic landscapes at your own pace.
Local Customs Options
- Downhill Skiing and Snowboarding Etiquette: When visiting the area during winter, it’s customary to adhere to local skiing and snowboarding customs that emphasize safety and courtesy on the slopes.
- Local Farm-to-Table Dining Traditions: Embrace the region’s farm-to-table dining culture by supporting local eateries that highlight Vermont’s fresh, seasonal ingredients.
- Community Holiday Celebrations: Participating in community-driven holiday events and parades reflects the region’s warm, welcoming spirit during festive seasons.
- Respect for Natural Landscapes: Maintaining environmental awareness and respectful outdoor practices is a valued custom here, ensuring the scenic beauty remains pristine for future visitors.
Frequently Asked Questions About Middlebury?
1. What are the top vacation rentals in Middlebury?
There are a lot of options in Middlebury. If you plan on staying in the Middlebury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlebury:
- Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
- Custom Home just minutes from Middlebury
- Experience Vermont charm! Up to 5 bedrooms available Please inquire for rates
- Large And Luxurious Farmhouse - Close To Town And College!
- Mountain-view House ~ Mins To Middlebury, Flex Cancellation Policy
- Middlebury, VT Newly renovated four bedroom Luxury Home (sleeps 8)
- Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury
- Upscale 4BR Cottage Walk to Middlebury College & Town Hot Tub Pet-Friendly
- Downtown Middlebury River House
- Charming, updated 3-bedroom farmhouse minutes from Middlebury with Wi-Fi & AC
2. Which vacation homes in Middlebury are best for families?
If you are looking for a family-friendly vacation home in Middlebury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlebury:
3. How many Rentbyowner vacation rentals are available in Middlebury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 46 in the Middlebury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middlebury.
4. What is the cancellation policy for vacation rentals here?
The cancellation policy varies depending on the specific property listing. It is recommended to review the terms provided during your booking process or contact the owner directly for detailed information regarding cancellations and potential refunds.
5. How do I confirm my reservation at a vacation rental in this area?
Once you select your preferred rental, you can complete the booking through the online platform. Confirmation details are typically sent via email, but it’s a good idea to verify with the property owner if you have any special requests or concerns.
6. Are there any specific check-in or check-out times I should be aware of?
Check-in and check-out times are determined by each property listing. Be sure to review these details before booking, and contact the host if you need to arrange early check-in or late check-out.
7. What amenities can I expect in vacation rentals around this destination?
Amenities vary by property but often include essentials such as Wi-Fi, kitchen facilities, parking, and outdoor spaces. For specific amenities, consult the individual listing details or reach out to the owner before booking.
8. Is there a secure way to pay when booking a vacation rental in the region?
Payments are generally handled securely through the booking platform, which supports various trusted payment methods. Always ensure that your transaction is completed through official channels to protect your personal and financial information.
Middlebury Top Rated Vacation Rentals
US $177/Night
For 7 Nights US $1,239
