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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 $799, price is now $735 per person
$735
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,088, price is now $902 per person
$902
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 3-star 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.
The Vesper

The Vesper

3 out of 5
Price was $1,003, price is now $901 per person
$901
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 3-star B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Price was $987, price is now $906 per person
$906
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $799, price is now $737 per person
$737
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 Fire Tower are located nearby.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Price was $909, price is now $840 per person
$840
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $900, price is now $834 per person
$834
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Price was $862, price is now $801 per person
$801
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Price was $839, price is now $781 per person
$781
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $812, price is now $758 per person
$758
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Stay at this 3.5-star beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $848, price is now $795 per person
$795
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,023, price is now $961 per person
$961
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and 8 hot tubs. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.

3-4 Night Vacations in Wilderness Trails

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $434, price is now $352 per person
$352
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,210, price is now $1,064 per person
$1,064
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
Price was $1,003, price is now $901 per person
$901
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $600, price is now $477 per person
$477
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)

5-7 Night Vacations in Wilderness Trails

Price found within the past 48 hours. Click for updated prices.
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 $644, price is now $534 per person
$534
per person
Nov 13 - Nov 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,259, price is now $1,135 per person
$1,135
per person
Nov 2 - Nov 7
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Wilderness Trails Last Minute Hotel Deals

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
White River Inn and Suites
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
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Super 8 by Wyndham White River Junction
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road, West Lebanon, NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in ...
Fireside Inn & Suites West Lebanon
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
1119 Quechee Main Street, Quechee, VT
Stay at this 3-star 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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Woodstock Inn & Resort
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr, White River Junction, VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Holiday Inn Express Hotel & Suites White River Junction by IHG
See all 2,995 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.