
House vacation rentals in Middlebury
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Top-rated house rentals in Middlebury
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Lake Dunmore Retreat 15 min to Middlebury College
Directly on the shore of Lake Dunmore, our lakefront getaway is a peaceful escape 15 minutes from Middlebury College. Whether you're visiting campus, celebrating graduation, or simply looking for a quiet retreat in nature, this home offers the perfect balance of lakefront relaxation and easy access to town. Spring is a beautiful time on Lake Dunmore. Enjoy mornings with coffee overlooking the water, take a walk along nearby trails, or explore the food scene and shops in downtown Middlebury.

Purple Door Cottage in the heart of Middlebury!
Purple Door Cottage is located in the heart of Middlebury on a peaceful side street. Completely renovated, AC & heat everywhere, lots of comfy beds, great deck with grill and fire ring, fast WiFi, king bedroom for the parents, fun guest room with 1 queen, 1 full & 1 twin, full bath & 1/2 bath. Walk to restaurants, shops, grocery stores, and even the College! Incredibly well designed home can comfortably accommodate a couple or a crowd! Brand new 55" Smart TV, new beds, linens, sofas, etc.

The Little House
You will be close to everything the village of Middlebury has to offer when you stay at this centrally-located, light-filled home. A short walk to Middlebury's coffee shops, retail stores, and restaurants. Very close to Middlebury College and just minutes from hiking, biking, skiing, and many other outdoor activities in the mountains and on the shores of Lake Dunmore or Lake Champlain. Perfect for a quiet stay in town or as an adventure home base. Off-street parking for two cars.

Middlebury Gem open concept, 5 minutes from town
This home is in the middle of Middlebury and within walking distance to everything. It is perfect for just two or a large group or family. This open concept was completely remodeled in 2020, it has an amazing fully equipped commercial kitchen, just installed A/C on all floors and 3 large bedrooms, 2.5 baths and a great gathering and living space and great front porch and back deck. The living area, kitchen and dining are downstairs and all three bedrooms upstairs.

Sunny Waitsfield Retreat, Views on 4 Private Acres
Incredible views from this fantastic house set on 4 acres central to all activities in the Valley - hiking, biking, skiing, fun at the river. A mile to downtown Waitsfield for groceries, shopping, etc. The house gets tremendous sun and all rooms have an exceptional view of the mountains, which are spectacular year round. The kitchen has everything you need for cooking, and there’s also a gas grill. Spend the day out exploring and then relax on the deck!

Dramatic Views at the Above the Clouds Guesthouse
As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Walk Everywhere and Enjoy a Historic Vermont Home
This historic 1860's home has been uniquely renovated to feature it's history combined with modern comfort. The kitchen is the focal place in the home which opens into the dining room. Watch the sunset from the back deck or while soaking in the hot tub! Original wood floors, tin ceilings, doors/door handles, etc. will take you back in time. This oasis in town provides back yard gardens and walking distance to downtown shops/restaurants.

Entire House in Middlebury - Walk Everywhere
An entire, charming, turn-of-the-century Victorian in the heart of downtown Middlebury, Vermont all to yourself! A short distance from Main Street, you are within walking distance to downtown boutiques, restaurants, art galleries, and Middlebury college. A fully outfitted, newly remodeled kitchen gives you the freedom to prepare your own meals. Two king size beds and all the beds are new, ensuring a comfortable sleep!

Lincoln house cottage
This is a charming home with butlers kitchen King suite sleep number bed large walk in shower Open floor plan living dining area very charming to the views Powder room off the living area Beautiful large covered porch overlooking the private yard and gardens fenced in yard great for dogs WiFi perfect for remote working Close to amazing skiing mad river Sugarbush Across from new haven river much more

Pristine Cottage, Grand Piano, Massage Studio
Meticulously clean, custom built cottage with grand piano & massage studio on property. Beam ceilings, wood floors, oriental carpets, & lots of art. Complete Kitchen Shower with shampoo, conditioners & body wash provided. New private deck, tables & chairs... outside art work. Swedish Massage with steamed towels & hot stones available in log cabin on site discounted to $70 for visiting guests

cozy home for a relaxing fall getaway
This newly Renovated Home has everything you will need to enjoy your stay with us. It’s a private home with 2 bedrooms, 2 bathrooms, full size washer and dryer, sitting area, cozy living room, spacious screen porch which is a great place to read or enjoy a meal, also a modern kitchen open to the dining room with a beautiful fireplace and sitting area.

In the heart of Middlebury, a modern farmhouse
This beautifully RENOVATED 3BR, 1.5 bath home merges its FARMHOUSE HERITAGE with MODERN décor and comforts. It is perfectly located on SOUTH STREET, perhaps the most sought-after address in Middlebury because it is nestled right between the heart of campus and this quintessential New England town. Both are just under a 5 min walk away.
Popular amenities for Middlebury house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Trail Creek - ski home!

TheGrizz! Shuttle on/off!

Ranch at Mendon Mt Orchards

Charming Sugarbush Standalone Condo

Dana Road House Sunlit VT Country Home w/HotTub

Stunning Mountain Top Cabin

EPIC Stowe Getaway - Great For Families & Friends
Weekly house rentals

3 story contemporary log cabin

Renovated East Middlebury House

The Looking Glass, a modernistic escape

Boutique Vermont Friends Farmhouse Fully Remodeled

Cornwall 1820 Farmhouse

Golden Hour on Lake Dunmore; Near Middlebury

Comfortable, sunny artist home

Home in Middlebury - Meadow Ranch at Fenn Farm
Private house rentals

Unique Serenity - 10 mins from Middlebury College

Vermont Country Guest Cottage

Sky Zen - Ridgeline Retreat

Lakefront Retreat 20 minutes from Middlebury

Upscale 4BR Cottage | Walk Downtown | Hot Tub

Modernist Cabin with mountain views, Bauschaus VT

Quiet Contemporary Farmhouse

Scotch Hill Cabin
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Lake George
- Okemo Mountain Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Fox Run Golf Club
- Stowe Mountain Resort
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Dartmouth College
- University of Vermont
- Adirondack Extreme Adventure Course
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Adirondak Loj
- Shelburne Museum
- Middlebury College
- Boyden Valley Winery & Spirits
- Warren Falls
- Shelburne Vineyard
- Trout Lake
- Lake Champlain Chocolates




