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Compare 2,148 hotels in Town of Olive with room rates, reviews, and availability. Most hotels are fully refundable.

3 bedrooms, WiFi, bed sheets
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Boiceville
9.6 out of 10, Exceptional, (5)
"The cabin was private, cozy, and had enough room for all our 6 guests to sleep comfortably. Fire pit in the backyard was a nice touch & the stars were amazing out there! Arton communicated promptly & we really enjoyed the cabin! Thanks again. "
United States
Bryan M.
$476 nightly
The price is $533
Nov 16 - Nov 17
Total with taxes and fees
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Exterior
West Wing - a unique private space w/patio

West Wing - a unique private space w/patio

Shokan
9.8 out of 10, Exceptional, (20)
"What a wonderful find! It was cozy, clean, beautiful, and the owner so kind and welcoming. I am only sorry we were staying for one night...next time we will definitely make a few day visit out of it. Perfect! "
United States
maureen
$158 nightly
The price is $177
Nov 17 - Nov 18
Total with taxes and fees
West Wing - a unique private space w/patio
Fridge, microwave, oven, stovetop
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Olivebridge
10.0 out of 10, Exceptional, (45)
"Very cute and cozy cottage! The hosts were very kind and responsive to messages. Very convenient place to stay to check out Woodstock!"
United States
Grace R.
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan
10.0 out of 10, Exceptional, (52)
"Nice place. Beautiful seroundings"
United States
Pierre B.
Relaxing Catskill Mountain Cottage.
Terrace/patio
High Point Mtn House ~ Celebrate Spring on the Mtn! Privacy! Gorgeous VIEWS!

High Point Mtn House ~ Celebrate Spring on the Mtn! Privacy! Gorgeous VIEWS!

Olivebridge
9.8 out of 10, Exceptional, (24)
"My friends and I were looking for a place for 8 of us to enjoy the weekend and it was awesome. The house location has one of the most beautiful sights of any VRBO house I've stayed at. Between the incredible audio systems, furniture layout, overall living room aesthetics, and living room windows designed to take advantage of the beautiful view, the interior was ideal for our group. The host was in constant communication with us and gave clear directions for entering and leaving the house. Highly...
United States
John K.
High Point Mtn House ~ Celebrate Spring on the Mtn! Privacy! Gorgeous VIEWS!
Exterior
Catskills Retreat on 10 Acres w/ Private Creek

Catskills Retreat on 10 Acres w/ Private Creek

Olivebridge
10.0 out of 10, Exceptional, (3)
"Loved our visit, would definitely stay again! "
United States
Marci R.
Catskills Retreat on 10 Acres w/ Private Creek
Fridge, microwave, oven, stovetop
Charming 2-bedroom cottage on private 4 acres with modern amenities

Charming 2-bedroom cottage on private 4 acres with modern amenities

Olivebridge
Charming 2-bedroom cottage on private 4 acres with modern amenities
Fridge, microwave, oven, stovetop
Atomic Ranch - MCM One Level in Olivebridge. Great Outdoor Space!

Atomic Ranch - MCM One Level in Olivebridge. Great Outdoor Space!

Olivebridge
10.0 out of 10, Exceptional, (1)
$537 nightly
The price is $601
Nov 17 - Nov 18
Total with taxes and fees
Atomic Ranch - MCM One Level in Olivebridge. Great Outdoor Space!
Terrace/patio
Cozy Cabin in the Woods By Ashokan Reservoir

Cozy Cabin in the Woods By Ashokan Reservoir

3.0 star property
Olivebridge
2.0 out of 10, (1)
Cozy Cabin in the Woods By Ashokan Reservoir
Terrace/patio
Rose Meadow: Quiet 1800s Farm House

Rose Meadow: Quiet 1800s Farm House

2.0 star property
Olivebridge
9.0 out of 10, Wonderful, (2)
"Us: 6 men in the 60s looking for a nice home for our annual summer getaway weekend. Home (inside): Very nice! Excellent flow throughout the house. Nice size kitchen, dining area and family room. Well appointed and furnished nicely. Bedrooms: Excellent variety of bedrooms and sleeping locations. Master bedroom/bathroom is very nice and large. Stairs: Not good. Sturdy but not up-to-code and difficult for tall people. Home (outside): Needs quite a bit of weed-whacking and cleanup. Needs better...
United States
Mitchell B.
Rose Meadow: Quiet 1800s Farm House
Private kitchen
Fully Furnished 1BR Apt – Ideal for Traveling Professionals

Fully Furnished 1BR Apt – Ideal for Traveling Professionals

2.0 star property
Shokan
Fully Furnished 1BR Apt – Ideal for Traveling Professionals
Smart TV, fireplace, books, music library
Catskills Family Hideaway

Catskills Family Hideaway

Olivebridge
10.0 out of 10, Exceptional, (14)
"Welcoming house in a beautiful setting. We will return!"
United States
Katherine T.
Catskills Family Hideaway
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3.0 star property
Hunter
9.2 out of 10, Wonderful, (807)
"We had great time room was very clean and staff was very friendly and helpful definitely recommend "
United States
Muhammad
$188 nightly
The price is $203
Nov 23 - Nov 24
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Premium bedding, down comforters, Tempur-Pedic beds, in-room safe
AutoCamp Catskills

AutoCamp Catskills

5.0 star property
Saugerties
9.0 out of 10, Wonderful, (432)
"Clean room & pet friendly hotel"
United States
Leslie
$169 nightly
The price is $190
Dec 8 - Dec 9
Total with taxes and fees
AutoCamp Catskills
Exterior
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2.0 star property
Hunter
9.2 out of 10, Wonderful, (314)
"Wonderful resort, clean , great facilities friendly staff "
United States
Tracy
$218 nightly
The price is $235
Nov 18 - Nov 19
Total with taxes and fees
Kaatskill Mountain Club at Hunter Mountain
Terrace/patio
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
Kingston
7.6 out of 10, Good, (1001)
"The room was great—clean. The restaurant was great—the food was tasty. The staff was exemplary. I would definitely stay here again."
United States
Youland
$106 nightly
The price is $118
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Kingston Hotel And Conference Center
Superior Room, Fireplace, River View | Egyptian cotton sheets, premium bedding, down comforters, minibar
Woodstock Way Hotel

Woodstock Way Hotel

4.0 star property
Woodstock
9.6 out of 10, Exceptional, (205)
"Room was great, highly recommend staying here! "
United States
Jared E
$277 nightly
The price is $305
Nov 17 - Nov 18
Total with taxes and fees
Woodstock Way Hotel
View from property
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 star property
Kingston
8.8 out of 10, Excellent, (93)
"The rooms were clean and the view was great. "
United States
Cristino
$237 nightly
The price is $266
Nov 20 - Nov 21
Total with taxes and fees
Hutton Brickyards Riverfront Hotel + Venue
Front of property
Beekman Arms Hotel

Beekman Arms Hotel

3.5 star property
Rhinebeck
8.4 out of 10, Very Good, (785)
"Great place to stay in town with a historic atmosphere."
United States
Lisa
$154 nightly
The price is $175
Dec 12 - Dec 13
Total with taxes and fees
Beekman Arms Hotel
View from property
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3.0 star property
Kingston
8.8 out of 10, Excellent, (772)
"Nice big room and friendly staff "
United States
Marvin
$111 nightly
The price is $124
Nov 23 - Nov 24
Total with taxes and fees
Residence Inn by Marriott Kingston
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
"Very clean and modern hotel for the price. Safe area, very comfortable beds, large rooms. Stayed here before and forgot, when we pulled up we were excited. We remembered how great it was! Definitely would stay again. Not far from New Paltz so a great choice if closer hotels are booked. Worth the extra 7 min drive. "
Kristen 1-night trip
Posted 1 day ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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