A large, historic building with a symmetrical facade, green shutters, and a central entrance with steps leading up to it.

Chalets in Dutchess County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Dutchess County chalets

Exterior

1. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (31 reviews)
The price is SAR 488
SAR 835 total
includes taxes & fees
3 Sep - 4 Sep
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Exterior

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

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (22 reviews)
"One of the best cabins I have been to with family, kids had great time and wife also loved the vibe. So clean and it feels like a home away from home 😊 highly recommend it for everyone, worth it! I am going go visit again with friend's for sure!! I would say everything u can think about is ten on ten ⭐️"
United States
Rahul
The price is SAR 824
SAR 1,282 total
includes taxes & fees
3 Sep - 4 Sep
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Exterior

3. Cozy Silo with Sunset Mountain Views near Woodstock

Cozy Silo with Sunset Mountain Views near Woodstock
Willow
10.0 out of 10, Exceptional, (21 reviews)
"Spectacular location, great place to stay, and a wonderful host"
United States
Dennis T.
Cozy Silo with Sunset Mountain Views near Woodstock
Outdoor dining

4. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is SAR 443
SAR 764 total
includes taxes & fees
17 Sep - 18 Sep
Jessie's Harvest House
Outdoor dining

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

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Outdoor dining

6. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
The price is SAR 353
SAR 654 total
includes taxes & fees
2 Sep - 3 Sep
Jessie's Harvest House Suite
Property grounds

7. Rustic Log with Pool Game room Amazing koi pound just mins from Hunter Mountain

Rustic Log with Pool Game room Amazing koi pound just mins from Hunter Mountain
Elka Park
9.4 out of 10, Exceptional, (8 reviews)
"Great place for a big crowd, we loved the pool table and how close it was to hunter mountain!"
United States
Ryan H.
Rustic Log with Pool Game room Amazing koi pound just mins from Hunter Mountain
Exterior

8. CHALET with INDOOR POOLHOUSE base of HUNTER mountain

CHALET with INDOOR POOLHOUSE base of HUNTER mountain
Lanesville
9.6 out of 10, Exceptional, (8 reviews)
"We had 45 birthday with 6 couples and it was perfect.It is a great place for a large group. "
United States
Chris B.
CHALET with INDOOR POOLHOUSE base of HUNTER mountain
Exterior

9. The Hunter Chalet

The Hunter Chalet
Hunter
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful home looking forward to more future stays."
United States
Ruben L.
The Hunter Chalet
Exterior

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

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
Architect-Designed Dome on Private 7-Acre Retreat
Outdoor dining

11. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is SAR 443
SAR 764 total
includes taxes & fees
17 Sep - 18 Sep
Jessie's Harvest House
Exterior

12. Private Chalet less than 1 mile to Ski Resort

Private Chalet less than 1 mile to Ski Resort
Lanesville
9.8 out of 10, Exceptional, (10 reviews)
Private Chalet less than 1 mile to Ski Resort
Exterior

13. Never Lonesome Hunter: Smart 4bd Getaway near Mtn

Never Lonesome Hunter: Smart 4bd Getaway near Mtn
Hunter
10.0 out of 10, Exceptional, (5 reviews)
"We loved our stay!"
United States
Georgie P.
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
Outdoor dining

14. Lakefront Chalet with Private Dock

Lakefront Chalet with Private Dock
Athens
9.8 out of 10, Exceptional, (78 reviews)
"We had a wonderful time. Weather was great (really hot and humid some days) so the grandkids enjoyed the lake very much.."
United States
Karen O.
Lakefront Chalet with Private Dock
Exterior

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

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
New Paltz
10.0 out of 10, Exceptional, (17 reviews)
"Fabulous! Would definitely go back."
United States
Christine D.
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Outdoor dining

16. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is SAR 443
SAR 764 total
includes taxes & fees
15 Sep - 16 Sep
Jessie's Harvest House
Exterior

17. Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach

Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach
Monterey
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful house my friends and I loved it there perfect cozy cabin vibes :) "
United States
Kamille N.
Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach
Exterior

18. 5 Star Gorgeous Cliffside Chalet w Panoramic Views

5 Star Gorgeous Cliffside Chalet w Panoramic Views
Tannersville
10.0 out of 10, Exceptional, (2 reviews)
"We thoroughly enjoyed our time at the Cliffside Chalet! The home is so thoughtfully curated and beautifully maintained. It is clearly well loved!The view is spectacular, easily enjoyed from the hot tub. The home is well situated nearby many hiking trails and hunter Mountain. It’s also right across from Deer Mountain Inn, a fabulous restaurant and bar!We cannot wait to plan another visit!"
United States
Harry K.
5 Star Gorgeous Cliffside Chalet w Panoramic Views
Terrace/patio

19. Catskill Chalet: Hunter Mtn Ski Chalet w/Spa

Catskill Chalet: Hunter Mtn Ski Chalet w/Spa
Tannersville
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay at this lovely cozy home in the Catskills during our visit to the Rhinebeck sheep and wool festival (about an hour away). The views in this area were superb during the peak autumn season. The home was clean and had every amenity one could think of. The hot tub was clean and relaxing. Catherine was easy to get in contact with and very responsive. Although, all information about our stay was very thorough and organized we didn't have many questions. Will definitely consider...
United States
Katie K.
Catskill Chalet: Hunter Mtn Ski Chalet w/Spa
Exterior detail

20. Luxury 30-Day+ Hunter Mountain 3BR Condo—Bright, Quiet, Spacious

Luxury 30-Day+ Hunter Mountain 3BR Condo—Bright, Quiet, Spacious
Hunter Highlands
Luxury 30-Day+ Hunter Mountain 3BR Condo—Bright, Quiet, Spacious
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.
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Top Dutchess County Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

8/10 Good
"Rooms were clean and the beds were comfy. Even though the hotel seemed busy, didn’t hear a lot of commotion once inside the room. The rooms were in need of some renovations and could def use a refresh, but completely livable. The bathroom was much smaller than expected. Really disliked that when taking a shower, large amounts of water gushed from the faucet and not out of the shower head (such a waste of water!). Even so, there was plenty of water coming out of the shower head itself. Also, the water never got hot from the sink - the best I could do was a luke warm to wash my face even after running the water for several mins. The breakfast buffet was a welcome meal in the morning. It was hot and well stocked with limited options that were tasty. They have two, single cup, coffee machines that grind a fresh cup every time and are avail for use all day. You may have to wait a min to brew a cup, but worth the extra time."
Penny 3-night trip
Posted 1 hour ago
Holiday Inn Express Poughkeepsie by IHG