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Pawling Vacations

Pack those stellar shades. We have Pawling vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Pawling – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pawling vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Pawling

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Pawling vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Pawling well.

Top Hotel Deals

See all 108 Hotels in Pawling
Station Inn Pawling

Station Inn Pawling

7 Memorial Avenue, Pawling
3.5 out of 5.0

Situated in Pawling, this guesthouse is close to John Kane House. Area attractions also include Whaley Lake and Thunder Ridge Ski Resort.

$149

$149
Hawthorn Suites by Wyndham Fishkill/Poughkeepsie Area

Hawthorn Suites by Wyndham Fishkill/Poughkeepsie Area

14 Schuyler Blvd, Fishkill
3.5 out of 5.0

Situated in the business district, this hotel is 4.4 mi (7.1 km) from Hudson Valley Research Park and within 16 mi (25 km) of Vassar College and Marist College. ...

$81

$81
Crowne Plaza Danbury

Crowne Plaza Danbury

18 Old Ridgebury Road, Danbury
4.0 out of 5.0

Situated near the airport, this hotel is 1.1 mi (1.8 km) from Matrix Conference and Banquet Center and within 3 mi (5 km) of Ives Concert Park and Richter Park ...

$88

$88
Residence Inn by Marriott Poughkeepsie

Residence Inn by Marriott Poughkeepsie

2525 South Rd, Poughkeepsie
3.5 out of 5.0

Situated in Poughkeepsie, this aparthotel is within 1 mi (2 km) of Locust Grove and Casperkill Golf Club. McCann Golf Course and Poughkeepsie Galleria are also ...

$110

$110
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

15 Milestone Road, Danbury
4.5 out of 5.0

Situated in Danbury, this hotel is 1 mi (1.5 km) from Matrix Conference and Banquet Center and within 3 mi (5 km) of Ives Concert Park and Richter Park Golf ...

$129

$129
Ramada Fishkill

Ramada Fishkill

542 Route 9, Fishkill
3.5 out of 5.0

Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Fishkill Golf Course, and Blodgett Memorial Library. SplashDown Beach is ...

$79

$79
La Quinta Inn & Suites Danbury

La Quinta Inn & Suites Danbury

116 Newtown Road, Danbury
3.0 out of 5.0

Situated in Danbury, this hotel is within 1 mi (2 km) of Berkshire Shopping Center and Still River Greenway. Danbury Railway Museum and Candlewood Plaza Shopping ...

$76

$76
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2361 South Rd, Poughkeepsie
3.0 out of 5.0

Situated in the suburbs, this hotel is 0.2 mi (0.3 km) from Casperkill Golf Club and within 3 mi (5 km) of Locust Grove and McCann Golf Course. Poughkeepsie ...

$109

$109
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

100 Westage Business Center Dr., Fishkill
3.5 out of 5.0

Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum and Blodgett Memorial Library. Fishkill Golf Course and SplashDown Beach ...

$99

$99
Buttermilk Falls Inn

Buttermilk Falls Inn

220 North Road, Milton
4.5 out of 5.0

Situated in the mountains, this spa hotel is within 6 mi (10 km) of Walkway Over the Hudson State Historic Park, Mid-Hudson Bridge, and Marlboro Free Library. ...

$250

$250

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.