A mountainous landscape with autumn foliage.

Chalets in Town of Olive

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Town of Olive chalets

A log cabin with a porch, a staircase, and a garage.

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

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.2 out of 10, Wonderful, (35 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
The price is AED 477
AED 817 total
includes taxes & fees
14 Oct - 15 Oct
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

2. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is AED 433
AED 739 total
includes taxes & fees
20 Oct - 21 Oct
Jessie's Harvest House
A rustic cabin with a green awning, surrounded by autumn foliage.

3. 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
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful stay!"
United States
Bernice
The price is AED 794
AED 1,185 total
includes taxes & fees
3 Nov - 4 Nov
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
A cabin with a deck, a fire pit, and a flag.

4. 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)
"Cozy stay for our family of four!"
United States
Kasey S.
Private Chalet less than 1 mile to Ski Resort
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

5. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is AED 433
AED 739 total
includes taxes & fees
19 Oct - 20 Oct
Jessie's Harvest House
A two-story white house with a porch, a small front yard, and a clear blue sky.

6. Catskill getaway near Woodstock, Hunter, Hudson

Catskill getaway near Woodstock, Hunter, Hudson
Palenville
10.0 out of 10, Exceptional, (1 review)
"The house is very large and the bedrooms are generous in size and easily accommodated our party of 8. We appreciated the garage parking for two cars, the welcome note and the bottle of wine from the host. Stanley was very responsive to my questions and was very accommodating to ensuring that the driveway was plowed and the garbage from the previous tenants was picked up despite the snowstorm. The Keurig coffee was a welcome addition to our stay. Please note that purchasing your own drinking...
United States
Teodora M.
Catskill getaway near Woodstock, Hunter, Hudson
A two-story building with a flat roof and a small tower-like structure on the roof.

7. 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
A deck with outdoor furniture overlooking a lake and hills.

8. The Hunter Chalet

The Hunter Chalet
Hunter
10.0 out of 10, Exceptional, (10 reviews)
The Hunter Chalet
A rustic cabin with a porch, surrounded by dense forest.

9. 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
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

10. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is AED 345
AED 636 total
includes taxes & fees
21 Oct - 22 Oct
Jessie's Harvest House Suite
A modern house with a sloped roof, large windows, and a stone foundation.

11. 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
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

12. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is AED 433
AED 739 total
includes taxes & fees
19 Oct - 20 Oct
Jessie's Harvest House
A large, two-story house with a steeply pitched roof, a wooden deck, and a stone foundation.

13. Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Big Indian
9.8 out of 10, Exceptional, (28 reviews)
"Room was spotless and amenities were great."
United States
Richard
The price is AED 1,517
AED 3,119 total
includes taxes & fees
19 Oct - 20 Oct
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
A snow-covered deck with a table and chairs, surrounded by trees and string lights.

14. Luxe Party Retreat: Ski Pool Karaoke Game Movie

Luxe Party Retreat: Ski Pool Karaoke Game Movie
Jewett
10.0 out of 10, Exceptional, (2 reviews)
"Super fun home with a lot of bells and whistles!"
United States
Bennett Z.
Luxe Party Retreat: Ski Pool Karaoke Game Movie
A wooden cabin with a red door and multiple windows, surrounded by trees and snow.

15. Cozy Silo with Sunset Mountain Views near Woodstock

Cozy Silo with Sunset Mountain Views near Woodstock
Willow
10.0 out of 10, Exceptional, (22 reviews)
Cozy Silo with Sunset Mountain Views near Woodstock
A snow-covered deck with a fire pit, a chair, and a table with drinks and a game box.

16. Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace

Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
Lexington
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed a week here with our two daughters and their husbands. The chalet was fantastic, as was the scenery. highly recommend this location."
Canada
Steven K.
The price is AED 1,917
AED 3,229 total
includes taxes & fees
8 Nov - 9 Nov
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
A hot tub in a backyard with a view of trees and a mountain.

17. Le View Chalet- HotTub, Sauna, Fire Pit, Geodome

Le View Chalet- HotTub, Sauna, Fire Pit, Geodome
Maplecrest
10.0 out of 10, Exceptional, (1 review)
"We had a great stay at Le View Chalet. The house was spotless when we arrived, and checking in with the smart lock was easy. It's well appointed with everything a family needs, and the house guide explained clearly how to use the appliances and amenities and what the house rules were, which saved us a lot of guesswork.Our kids loved running around the grounds, the geodome, and making smores around the campfire and spent plenty of time in the game room. We made good use of the hot tub and the...
United States
Sheng C.
Le View Chalet- HotTub, Sauna, Fire Pit, Geodome
A wooden sauna with a bench and a towel rack, leading to a view of a snowy landscape and mountains.

18. Le Chalet: Modern Design, Mountain views, Chef's Kitchen, Sauna & Hot Tub

Le Chalet: Modern Design, Mountain views, Chef's Kitchen, Sauna & Hot Tub
Prattsville
10.0 out of 10, Exceptional, (11 reviews)
"Our time at the Chalet was perfect from start to finish. The home was beautiful, and all the welcoming touches were lovely. My husband and I and our four boys enjoyed our stay tremendously, and we were so happy to have a chance to relax and reconnect as a family."
United States
Meghan F.
Le Chalet: Modern Design, Mountain views, Chef's Kitchen, Sauna & Hot Tub
A two-story stone house with a green exterior, a chimney, and a mailbox.

19. Never Lonesome Woodland Valley: Cozy 2bd Cottage!

Never Lonesome Woodland Valley: Cozy 2bd Cottage!
Phoenicia
9.4 out of 10, Exceptional, (12 reviews)
"The place was beautiful, spacious and cozy. Highly recommend it if you are looking for a quiet and relaxing time. "
United States
Gabriel
Never Lonesome Woodland Valley: Cozy 2bd Cottage!
A person sitting on a deck chair with a dog, overlooking a forested area with a fire feature.

20. Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit

Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit
Arkville
10.0 out of 10, Exceptional, (1 review)
"Clean, calming, everything functioning, nice new woodwork and good kitchen set up. AC is effective, superb lightening choices.. Great location, access to many places, in a quiet neighborhood. Would return here. infoor and outdoor."
United States
Gabor K.
Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit
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 Town of Olive Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Everything we needed for our stay, clean room and friendly staff, easy to park was a plus!! Idk how hotels are ranked but this is definitely better than a 2star in my opinion. I have been all over the place staying in hotels and this was a great experience!! Especially if all you need is a place to clean up and lay your head, that’s all we usually use hotels for because we are always on the go doing activities when needing a hotel!"
Richard 2-night trip
Posted 6 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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