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.
Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $1,348, price is now $1,202 per person
$1,202
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,482, price is now $1,282 per person
$1,282
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A 24-hour gym and barbecue grills are also provided.
Windham NY Escape

Windham NY Escape

3 out of 5
Price was $1,922, price is now $1,725 per person
$1,725
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
Luggage storage is available at this cabin. Take advantage of the free self parking.

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
$139 nightly
The price is $150 total per night
$150 total
Aug 18 - Aug 19
Total with taxes and fees
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
Emerson Resort & Spa

Emerson Resort & Spa

3.5 out of 5
5340 NY-28 Mount Tremper NY
$215 nightly
The price is $240 total per night
$240 total
Aug 2 - Aug 3
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. You'll appreciate the seasonal outdoor pool, bar/lounge, and coffee shop.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
$303 nightly
The price is $327 total per night
$327 total
Aug 5 - Aug 6
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Pool
Pet friendly
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
37 Alpine Rd Big Indian NY
$263 nightly
The price is $295 total per night
$295 total
Aug 2 - Aug 3
Total with taxes and fees
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 & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

2 out of 5
61 LIFTSIDE DR Hunter NY
$228 nightly
The price is $246 total per night
$246 total
Aug 27 - Aug 28
Total with taxes and fees
This smoke-free hotel features 2 hot tubs, an outdoor pool, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. You'll appreciate the sauna, bar/lounge, and laundry facilities.
Pool
Hot Tub
Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
$150 nightly
The price is $162 total per night
$162 total
Aug 9 - Aug 10
Total with taxes and fees
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.
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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.

Stay near popular Ashland attractions

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?
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Frequently asked questions

How much are vacation packages to Ashland?
Your travel daydreams can come true in Ashland for only $1,202. 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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