We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Middlebury Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    £180 Average
    |||
    |||
    £0£1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Middlebury area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Middlebury
    Sort by:
    Default
    Middlebury
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Middlebury VT - gorgeous home1 / 10
    (2)Excellent
    Middlebury
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Middlebury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Charming Cottage within walking distance of Middlebury College / Sleeps 41 / 13
    (12)Excellent
    Middlebury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Middlebury, Vermont 05753
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Remodeled Farmhouse close to Middlebury College1 / 20
    (7)Excellent
    Middlebury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Grill
    • Satellite TV
    • Patio
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Middlebury, Vermont 05753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    The following rentals are within 25 kilometres of Middlebury.
    The Swallow's Nest1 / 13
    (10)Excellent
    Brandon
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    • Parking
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Idyllically situated just south of Brandon, even the torrential rain one morning didn’t dampen the view or our enthusiasm. The property is as described, the photos accurate and...
    Reviewed 15 August 2017
    The highest compliment you can give a vacation-rental owner is returning, and that's exactly what we're doing. We've already reserved The Swallow's Nest for five days next July...
    See all reviews
    About this property
    Romantic spot, totally secluded, exceptional water and mountain views Situated on our organic farm, our lovely guest house is the perfect place for a weekend getaway, or extended vacation. 'The Nest' is surrounded by 50 acres of meadows and offers exceptional views of the Green Mountains and...
    View all property information
    Location Information
    Brandon, Vermont 05733
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    The Little House Vermont1 / 28
    (5)Excellent
    Brandon
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Satellite TV
    • Wi-Fi
    • Parking
    • Mountain Views
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Brandon, VT stay was a great base for visiting Killington, Woodstock and the southern scenic drive of 100. Be sure to visit the Cafe Provence when in Brandon. It was one of...
    Reviewed 18 June 2016
    Staying here for a few nights lifted our spirits from the moment we arrived. Kerrie and Russ made us feel like welcome friends at the outset, then quietly left us alone to...
    See all reviews
    About this property
    This is a special little hideaway just a five minute walk to our lovely downtown. Located in a quiet residential area, create your own retreat in this newly built art filled cottage. The bedroom is separated from the open concept living space by sliding barn doors. The en suite bathroom has a tub/...
    View all property information
    Location Information
    Brandon, Vermont 05733
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, Family Fun1 / 54
    (3)Excellent
    Ripton
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    River Stone Lodge a wonderful place to stay! Come and enjoy a Vermont vacation in a beautiful area in a fun and fabulous home! Sleeps 2-15. Great for 2-3 families wanting to spend time together or just for 2 for that Very special getaway. Fully Equipped home with everything you could need for a...
    View all property information
    Location Information
    Ripton, Vermont 05766
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
    Make Enquiry
    Panton
    4 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Waterfront
    • Parking
    • Washer
    • DVD Player
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A peaceful Vermont getaway awaits you at this 4-bedroom, 4-bathroom vacation rental house in Panton. Boasting over 3,800 square feet of well-appointed living space, this spacious home features an open floor plan and everything you need to feel at home! With stunning views of Lake Champlain and...
    View all property information
    Location Information
    Panton, Vermont 05491
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 13
    Make Enquiry
    Spectacular Log Cabin w/ Mountain Views near Lake1 / 28
    (13)Excellent
    Ferrisburg
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    • Hot Tub
    • Mountain Views
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winter Wonderland! 2 weekends left!!Beautiful log cabin home located on 56 acres with fabulous mountain and meadow views! 3 bedrooms, 2 1/2 baths, fully equipped kitchen, full size oven, microwave, fridge, stove, basic spices, ect. Washer & dryer,1 king, 2 queen beds, 2 twins beds and 1 queen pull...
    View all property information
    Location Information
    Ferrisburg, Vermont 05473
    Cabin Holiday Rental - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Middlebury rentals sent straight to your email!
    Get the List
    Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Housekeeping Included
    • DVD Player
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This expanded 2 story federal style cape cod has large living areas downstairs and all three bedrooms upstairs. The first floor includes a fully equipped open beam gourmet kitchen with eating area. Cabinets are fully stocked with everything you will need to serve a gourmet meal. A half bath is...
    View all property information
    Location Information
    Cornwall, Vermont 05753
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Incredible Mountain Views, Acreage to Roam & Play1 / 8
    (1)Excellent
    New Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2014
    The house is a unique design, all clean lines and modern comforts. There is plenty of natural light as the windows are large to show off the beautiful views. The location is...
    See all reviews
    About this property
    3500 Sq.Ft, 4 Bedrooms, 2 Bathrooms, Sleeps 9 The Red Studio House is a 3500 square-feet industrial modern home with 4 bedrooms and 2 baths. It was designed as an artist studio by a renowned VT architect and was the winner of the 2002 AIA Vermont Excellence in Architecture Award/Red...
    View all property information
    Location Information
    New Haven, Vermont 05491
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Ripton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Central Heating
    • Private Garden
    • Washer
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private get-away in the heart of the Green Mountains. Perfect for lovers of the outdoors, hikers, skiers, snowboarders, photographers, artists or for anyone who wants to disconnect from the routine and discover this peaceful place. 10 minutes drive to Snow Bowl and 15 minutes to Middlebury. The...
    View all property information
    Location Information
    Ripton, Vermont 05766
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Brandon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Parking
    • Waterfront
    • Porch
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy spectacular water views from every room in the house. There are 2 balcony openings from the upstairs bedrooms and wrap around deck on main level. You can feed the fish directly from the deck.! The house has 3 bedrooms - master has king bed and the other 2 bedrooms have queen beds. The...
    View all property information
    Location Information
    Brandon, Vermont 05735
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Mountain Views
    • Terrace
    • Balcony
    • Patio
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newer house directly on Lake Dunmore, back door is 50 feet from the water on a flat lot. Home has 2 bedrooms and a pull out sofa in the living room. Beautiful views galore. Home is located in a desirable cove with a private beach. We also have a dock that can accommodate a boat up to approx 23'....
    View all property information
    Location Information
    Salisbury, Vermont 05733
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Brandon
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the most interesting vacation rentals in Killington, VT, this converted 1955 motor home set on Lake Hortonia in the Vermont Lake Region has 2 bedrooms and will sleep 4. One bedroom has a full size bed the other bedroom is a bunk room, with 2 single beds. (These beds are best for someone...
    View all property information
    Location Information
    Brandon, Vermont 05732
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Addison
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Mountain Views
    • Central Heating
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Elmtucket, where you can come and get away from it all. Elmtucket is a beautiful 6 bedroom, 4 bathroom cape nestled on the shores of picturesque Lake Champlain. This home has something for everyone. With it's sprawling two acre open lot, 239 feet of level lake frontage, a dock for you to...
    View all property information
    Location Information
    Addison, Vermont 05491
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Salisbury
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished house and fully equipped kitchen. Large sun deck with grill and outdoor furniture. Close to Middlebury College and Bread Loaf Campus. Great Hiking up Moosalamoo and Lake Dunmore's Branbury beach is only half a mile down the road. Special rate for Bread Loaf School of English term....
    View all property information
    Location Information
    Salisbury, Vermont 05769
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Cornwall Carriage House1 / 6
    (3)Excellent
    Cornwall
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2017
    We had a fantastic stay at the Cornwall Carriage House. The hosts were always available and provided a spacious and well stocked home for our one week stay. The location is...
    Reviewed 12 August 2017
    I booked this carriage house for an anniversary weekend with my boyfriend. The views from the carriage doors frame the mountains perfectly, and we enjoyed having our morning...
    See all reviews
    About this property
    Located just 7 miles outside of Middlebury, offering privacy and expansive views of the Green Mountains. Newly built and furnished with quality and luxury in mind. A queen bed is located in the bedroom upstairs. There is also a futon couch upstairs as well as two day beds located on the first...
    View all property information
    Location Information
    Cornwall, Vermont 05753
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Monkton
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, eco-friendly lakefront cottage on a quiet little lake, halfway between Burlington & Middlebury Vermont. 1 bedroom (double bed), a queen-sized futon in the living room and a loft with two twin beds – sleeps 5-6. Indoor bath, hot shower and electric composting toilet. Private dock with...
    View all property information
    Location Information
    Monkton, Vermont 05673
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Monkton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quiet two bedroom on the outskirts of Monkton, Vermont features a large, private screen in back deck. It is 30 minutes from both Burlington (UVM) and Middlebury. Nestled in trees, secluded from the road, Hummingbird Lane winds off Rotax Road. This comfortable space offers a quiet retreat from...
    View all property information
    Location Information
    Monkton, Vermont 05473
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Monkton
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three (2) bedroom apartments in a big beautiful Vermont country home that can be rented together and connected together with common doors. The house sits well off the road -- can't be seen from the road -- surrounded by mature trees. All three apartments are completely updated with new appliances,...
    View all property information
    Location Information
    Monkton, Vermont 05473
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Enquiry
    Monkton
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: Beginning December 1, 2016, this property is only available for reservations of one week or longer. There are substantial discounts for weekly and monthly stays. It's a little like a very large treehouse -- big open windows and when you look out all you can see is the huge trees that...
    View all property information
    Location Information
    Monkton, Vermont 05473
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Monkton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two (2) bedroom apartments in a big beautiful Vermont country home that can be rented together and connected together with common doors. Both are completely updated with new appliances, newly refinished (or completely new hardwood) floors, quality furniture and quality beds, big open rooms with...
    View all property information
    Location Information
    Monkton, Vermont 05473
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    List your property
    Owner log in