Top Chalets in Town of Wappinger in 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Town of Wappinger chalets

1. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Gardiner

Heather G.

HK$2,460 total

includes taxes & fees

26 Aug - 27 Aug

2. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Carmel Hamlet

Brian S.

3. Architect-Designed Dome on Private 7-Acre Retreat

Dover Plains

4. Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

New Paltz

Christine D.

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Town of Wappinger Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Good breakfast. Good coffee. No carpet in rooms is a nice touch."

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good

"First-class hotel, except for the breakfast. My spouse and child waited for 40 minutes to be fed until they gave up and left. They observed other patrons not getting any breakfast, either. Probably just as well, as the prices were outrageously high (even if the service had been even remotely competent). The drive-thru window at Dunkin' Donuts provided better service and at much more reasonable prices. I would stay at the Doubletree again, but I would plan to avoid their restaurant at all costs."

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Everything was great...fun bar, very nice rooms with kitchen small living room area. But the reason we stayed was the Culinary Institute. The staff told us it was a 5 min walk, Please be advised it is not 5 min more like 10-15 min. The hill from the hotel is step and it's also steep to go up to the Culinary Institute. If your young its fine. But people who don't walk to well should expect to take and Uber maybe 7-10.00$ We took and Uber home because it was dark out after we had our dinner. You can pick up and Uber very easy by the students dorms."