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Wilderness Trails Vacation Packages

Wilderness Trails Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $694, price is now $562 per person
$562
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,718, price is now $1,352 per person
$1,352
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $867, price is now $689 per person
$689
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,549, price is now $1,236 per person
$1,236
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $906, price is now $818 per person
$818
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and a conference center. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Price was $1,163, price is now $1,052 per person
$1,052
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $647, price is now $586 per person
$586
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $856, price is now $777 per person
$777
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $942, price is now $858 per person
$858
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $858, price is now $782 per person
$782
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $742, price is now $678 per person
$678
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,196, price is now $1,092 per person
$1,092
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.

3-4 Night Vacations in Wilderness Trails

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $694, price is now $562 per person
$562
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,718, price is now $1,352 per person
$1,352
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $867, price is now $689 per person
$689
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,549, price is now $1,236 per person
$1,236
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)

5-7 Night Vacations in Wilderness Trails

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $1,077, price is now $996 per person
$996
per person
Dec 1 - Dec 8
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,614, price is now $1,472 per person
$1,472
per person
Dec 1 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,326, price is now $1,213 per person
$1,213
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,288, price is now $1,187 per person
$1,187
per person
Dec 1 - Dec 8
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)

Wilderness Trails Last Minute Hotel Deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Align Inn Vermont
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
1119 Quechee Main Street Quechee VT
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. ...
The Quechee Inn at Marshland Farm
See all 422 properties in Wilderness Trails
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.

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