Deals on vacations and trips to Ashland

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Ashland flight + hotel vacation packages

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

Hotel Vienna

2.5 out of 5
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Hudson (HCC)
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Hudson (HCC)
A restaurant and an outdoor pool are featured at this hotel. Enjoy the sauna and perks like free WiFi. A lobby fireplace, a picnic area, and luggage storage are also on offer.
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and barbecue grills are also provided.

Top Ashland hotels deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
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A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A lobby fireplace, a communal living room, and a library are also on offer.
Breakfast included
Pet friendly
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
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This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.
Pool
Breakfast included
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
37 Alpine Rd, Big Indian, NY
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This lodge features a restaurant, a sauna, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, a lobby fireplace, and a communal living room are also on offer.
Spa
Pet friendly
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR, Hunter, NY
Free Cancellation
Reserve now, pay when you stay
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A restaurant and an outdoor pool are featured at this hotel. Enjoy the sauna and perks like free WiFi. A lobby fireplace, a picnic area, and luggage storage are also on offer.
Pool
Free WiFi
The Roxbury at Stratton Falls

The Roxbury at Stratton Falls

2 out of 5
48 Co Rd 41, Roxbury, NY
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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A seasonal outdoor pool is also provided.
Pool
Breakfast included
Hotel Mountain Brook

Hotel Mountain Brook

4 out of 5
57 Route 23c, Tannersville, NY
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This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A bar/lounge and a library are also provided.
Breakfast included
Pet friendly
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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.

Popular places to visit

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?

Ashland Town Hall

Frequently asked questions

How much are vacation packages to Ashland?
Your travel daydreams can come true in Ashland for only $687. Our affordable package deals include flights and hotels, so they're bound to make booking nice and easy. The only thing you'll need to concentrate on is having a good time.
Where can I get the best vacation package deals for Ashland?
No matter how you like to travel, Travelocity can help you snap up the best Ashland package deal. All you need to do is select a combination from our 400 air carriers and 1,000,000 properties worldwide.
Why should I purchase my Ashland vacation package with Travelocity?
Because you'll never roam on your own if you book through us, and we offer 24/7 customer support and excellent service to boot. Add to that our Price Match Guarantee and tons of experiences and destinations to pick from. We're here to help you jet off on the vacation of a lifetime.
Can I save on my Ashland car rental if I combine it with hotels and flights?
You most certainly can --- combine your car, hotel and flight into an Ashland vacation package and you can save plenty. With so much to uncover in and around Ashland, that rental vehicle will make exploring a breeze. Once you're in the driver's seat, get out on the wide open road and make tracks to Times Square, a famous attraction approximately 110 mi from Ashland.
Which airport is best for Ashland?
Albany Intl. Airport (ALB) is where many vacationers touch down. It's located around 40 mi northeast from downtown Ashland. You can also check out the deals to Stewart Intl. Airport (SWF), which is 55 mi away from central Ashland.
Where should I stay when visiting Ashland?
Many people opt to hit the hay at the Ashland · Home Theatre, Game Room, Private Driving Range. It's a terrific base for your Ashland escape.

Photos of local treasures

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