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Overlook Mountain Trailhead Vacation Packages

Overlook Mountain Trailhead Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $1,127, price is now $939 per person
$939
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,510, price is now $1,243 per person
$1,243
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2 out of 5
Save 100% on your flight
Price was $4,789, price is now $3,960 per person
$3,960
per person
Dec 28 - Jan 2
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Book a stay at this family-friendly vacation home in Maplecrest. Enjoy free parking and a garden. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,962, price is now $1,643 per person
$1,643
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Amazing Hiking Cozy Home Close to Mountns Fireplace

Amazing Hiking Cozy Home Close to Mountns Fireplace

2 out of 5
Price was $1,947, price is now $1,646 per person
$1,646
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Stay at this vacation home in Prattsville. Enjoy free parking and a garden. Popular attractions Pratt Museum and Zadock Pratt Museum are located nearby.

5-7 Night Vacations in Overlook Mountain Trailhead

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $1,127, price is now $939 per person
$939
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,510, price is now $1,243 per person
$1,243
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2 out of 5
Save 100% on your flight
Price was $4,789, price is now $3,960 per person
$3,960
per person
Dec 28 - Jan 2
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,962, price is now $1,643 per person
$1,643
per person
Jan 2 - Jan 8
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)

Overlook Mountain Trailhead Last Minute Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions ...
Woodstock Way Hotel
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
Stay at this hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodstock Public Library and SweetHeart Gallery are located ...
Twin Gables of Woodstock
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St Woodstock NY
Book a stay at this luxury guesthouse in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions The Comeau Property and Woodstock ...
The Herwood Inn
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street Woodstock NY
Stay at this B&B in Woodstock. Enjoy free breakfast, free parking, and a garden. Popular attractions The Comeau Property and Woodstock Public Library are located ...
Morning Glory B n B Woodstock NY
The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

3 out of 5
48 Tannery Brook Rd Woodstock NY
Stay at this hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions SweetHeart Gallery and Woodstock Artists Association ...
The Woodstock Inn on the Millstream
The 212 Escape

The 212 Escape

3.5 out of 5
1659 NY-212 Woodstock NY
Book a stay at this family-friendly country house in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Bethel Woods Museum ...
The 212 Escape
See all 1,086 properties in Overlook Mountain Trailhead
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.