Exclusive Skyline Trail Vacation Deals

Skyline Trail vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Dewey

The Dewey

3.5 out of 5
Price was $855, price is now $681 per person
$681
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,183, price is now $839 per person
$839
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,012, price is now $783 per person
$783
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $1,235, price is now $969 per person
$969
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $859, price is now $684 per person
$684
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $847, price is now $683 per person
$683
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.

Frequently asked questions

How much are vacation packages to Skyline Trail?
Check out Travelocity's awesome $681 Skyline Trail package deal. With all the cash you save on your hotel stay and flights, you can splash out on some unforgettable luxury experiences. Watch out Skyline Trail, here you come!
Where can I get the best vacation package deals for Skyline Trail?
With as many as 400 air carriers and 1,000,000 properties around the world, it's hard to top Travelocity. Make the most of our extensive range and score an incredible package deal to Skyline Trail. Don't you love it when travel is that easy?
Why should I purchase my Skyline Trail vacation bundle via Travelocity?
We make traveling the world easy. Whether you're seeking a new destination to roam around or want to make sure you get the best price on offer, we're here to assist. Our 24/7 support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.

Top Skyline Trail hotel deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Feb 12 - Feb 13
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $129 total per night
$129 total
Jan 15 - Jan 16
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Skyline Trail
View all properties
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.