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Featured Cottages in Winhall

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Winhall VT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Dorset VT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington VT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Lake life at Woodford Cottage

Lake life at Woodford Cottage

Bennington VT
Guests of this cottage enjoy access to ski-in/ski-out access, laundry facilities, and barbecue grills. This ski cottage also has a garden.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester VT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)

Londonderry VT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Woodford VT
At this cottage, guests have access to barbecue grills.
Near Hiking & Skiing: Home in Wilmington!

Near Hiking & Skiing: Home in Wilmington!

3 out of 5
Wilmington VT
This cottage offers an outdoor pool, a sauna, and free WiFi in public areas. You can put free parking to good use if you drive. This smoke-free cottage also has barbecue grills.
Home with a spring-fed pond and mountain view.

Home with a spring-fed pond and mountain view.

Manchester VT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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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.

Hotel Options in Winhall

    Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

    Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

    Jamaica VT
    $1,176 nightly
    The price is $1,329 total per night from Jan 19 to Jan 20
    $1,329 total
    Jan 19 - Jan 20, 2026
    Total with taxes and fees
    9.6/10 Exceptional! (21 reviews)
    Pointe at Castle Hill Resort

    Pointe at Castle Hill Resort

    2940 State Route 103 Cavendish VT
    $142 nightly
    The price is $154 total per night from Jan 12 to Jan 13
    $154 total
    Jan 12 - Jan 13, 2026
    Total with taxes and fees
    8.6/10 Excellent! (927 reviews)
    Mount Snow Grand Summit Resort

    Mount Snow Grand Summit Resort

    89 Grand Summit Way West Dover VT
    $333 nightly
    The price is $366 total per night from Dec 23 to Dec 24
    $366 total
    Dec 23 - Dec 24
    Total with taxes and fees
    8.6/10 Excellent! (243 reviews)

Cottages

Book a cottage in Winhall
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winhall. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winhall better.

Cottage apartments in Winhall range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winhall
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winhall and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winhall cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winhall. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winhall Cottages essential information

Accommodation
149 Cottages
Lowest Price
$154
Highest Price
$1,329
Popular accommodation
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}, Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!, Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Lake life at Woodford Cottage, The Cairn, 1840s Cozy Stone Cottage, Pet Friendly, Vermont Country Cottage (Near Village), Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access, Near Hiking & Skiing: Home in Wilmington!, Home with a spring-fed pond and mountain view.