Search Deals onSkyline Trail Vacation Packages
Skyline Trail Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Hotel Brookmere & Arbor Spa
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4-star spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.
Lodges At Cresthaven
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4-star beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Million Dollar Beach and Hearthstone Point Campground are located nearby.
The Dewey
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Hasbrouck House
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Stone Ridge. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Prospect Berkshires
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 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 Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located nearby.
Battenkill Glamping Resort
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 5-star luxury lodge in Cambridge. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Eldridge Swamp State Forest and The Georgi Museum are located nearby.
Hampton Inn & Suites Albany Airport
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Kingston Carriage House
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4-star B&B in Kingston. Enjoy free breakfast, free WiFi, and in-room massages. Popular attractions Hudson River Maritime Museum and Trolley Museum of New York are located nearby.
Gideon Putnam Resort And Spa
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 4-star spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Saratoga Performing Arts Center and Saratoga Race Course are located nearby.
Homewood Suites By Hilton Schenectady
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rivers Casino & Resort and Museum of Innovation and Science are located nearby.
3-4 Night Vacations in Skyline Trail
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Skyline Trail
Price found within the past 48 hours. Click for updated prices.
Skyline Trail Last Minute Hotel Deals
FairBridge Inn Express
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 ...
Berkshire Mountain Lodge
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 ...
Quality Inn
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 ...
Berkshires Untold
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 ...
The Yankee, Trademark Collection by Wyndham
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 Black Swan Lee - Lenox, Ascend Hotel Collection
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 ...
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hampton Inn & Suites Berkshires-Lenox
445 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 helpful staff ...
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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Hotels Near Points of Interest in Skyline Trail
- Hotels near Lee Premium Outlets
- Hotels near Jacob's Pillow
- Hotels near Housatonic River
- Hotels near Berkshire Mountain Country Store
- Hotels near Goose Pond Reservation
- Hotels near Pyramid Lake
- Hotels near Wyndhurst Golf & Club
- Hotels near Glendale Falls
- Hotels near Wood's Pond
- Hotels near Herman Melville's Arrowhead
- Hotels near Otis Ridge
- Hotels near Chester Town Hall
- Hotels near Lee Library
- Hotels near Westfield River
- Hotels near Wahconah Falls State Park
- Hotels near Swift River
Car Rentals in Skyline Trail
- Car rentals in Upstate New York
- Car rentals in Lenox
- Car rentals in The Berkshires
- Car rentals in Williamstown
- Car rentals in Pittsfield
- Car rentals in Northampton
- Car rentals in Great Barrington
- Car rentals in Stockbridge
- Car rentals in Lee
- Car rentals in Westfield
- Car rentals in Appalachian Mountains
- Car rentals in Hancock
- Car rentals in Western Massachusetts
- Car rentals in Becket
- Car rentals in Otis
- Car rentals in Adams