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Skyline Trail Vacation Packages

Skyline Trail Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $748, price is now $550 per person
$550
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,645, price is now $1,308 per person
$1,308
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 3.5-star golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $1,167, price is now $997 per person
$997
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Scene One Movieland are located nearby.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,341, price is now $787 per person
$787
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,730, price is now $1,202 per person
$1,202
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,912, price is now $1,332 per person
$1,332
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $819, price is now $584 per person
$584
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was $1,178, price is now $847 per person
$847
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 3.5-star hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
Price was $1,075, price is now $776 per person
$776
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,013, price is now $736 per person
$736
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3 out of 5
Save 100% on your flight
Price was $1,470, price is now $1,140 per person
$1,140
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly cottage in Ghent. Enjoy free parking, in-room washers/dryers, and in-room fireplaces. Popular attractions High Falls Trail and Hudson Chatham Winery are located nearby.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $791, price is now $614 per person
$614
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.

3-4 Night Vacations in Skyline Trail

Price found within the past 48 hours. Click for updated prices.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $819, price is now $584 per person
$584
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,341, price is now $787 per person
$787
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
Price was $1,075, price is now $776 per person
$776
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,013, price is now $736 per person
$736
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)

5-7 Night Vacations in Skyline Trail

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $1,167, price is now $997 per person
$997
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,645, price is now $1,308 per person
$1,308
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,730, price is now $1,202 per person
$1,202
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,912, price is now $1,332 per person
$1,332
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)

Skyline Trail Last Minute Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
FairBridge Inn Express
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Quality Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Berkshires Untold
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street, Pittsfield, MA
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are ...
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
See all 1,730 properties in Skyline Trail
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.