Montgomery Cottages - Vacation Rentals in Middlebury
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Luxury Places to Stay in Middlebury
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Top-Rated Vacation Rentals with a Pool in Middlebury
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Pet-Friendly Vacation Rentals in Middlebury
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Large Vacation Homes & Villas in Middlebury
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Wheelchair Accessible Vacation Homes in Middlebury
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Middlebury Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Middlebury
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About Middlebury Vacation Rentals
With more than 1010 Middlebury vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Middlebury.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Middlebury, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Middlebury. Places to stay near Middlebury are 1119.59 ft² on average, with prices averaging US $429 a night.
Montgomerycottages makes it easy and safe to find and compare vacation rentals in Middlebury with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Middlebury
| Type | Count |
|---|---|
| Vacation Homes | 437 |
| Holiday Apartments | 111 |
| Cabin Rentals | 81 |
| Cottages | 56 |
| Hotels | 44 |
| Ski Chalet Rentals | 27 |
| B&B | 15 |
| Others | 8 |
| Resorts | 2 |
| Hostels | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Middlebury
★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Middlebury.
Weather in Middlebury
View the weather forecast for Middlebury before booking your Middlebury Vacation Rentals to confirm your best time to go.
Top Attractions Around Middlebury, VT
Montgomerycottages offers a large selection of top attractions around Middlebury. Research things to do on your vacation before you visit Middlebury.
Other Places to Stay Near Middlebury, VT
Middlebury Vacation Rental Frequently Asked Questions
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:
- Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
- Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
- Cozy Cottage, Private Lake with Picnic Area & Firepit
- Absolutely Fantastic Family Vacation Spot - Fox Meadow Lakefront
- Waterfront Ponds, Beautiful , 51 Acre Property Retreat
- Snowcreek Condo at Sugarbush Resort-2 beds/2 baths, slopeside
- Ski-on/Off, Slope Views, Mountainside Top Floor, Vaulted Ceilings, Gas Fireplace
- Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
- RECENTLY RENOVATED Private Chic Modern Mountain Home
- Doc's Lake house 1st floor, 2 bedroom apartment
How many vacation rentals have private pools in Middlebury?
There are 9 vacation rentals with private pools near Middlebury. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Middlebury?
Currently, the total number of properties listed in 2026 is over 1010 in the Middlebury area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Middlebury.
