A mountainous landscape with autumn foliage.

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Our top choices for Town of Olive holiday rentals

A wooden deck with a bench, surrounded by a forested area.

1. West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (36 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
The price is £154
includes taxes & fees
19 Oct - 20 Oct
West Wing - a unique private space w/patio
A living room with a sofa, television, and plants.

2. Mid-Century Ranch * One-Level Living * Quiet Garden

Mid-Century Ranch * One-Level Living * Quiet Garden
Olivebridge
The price is £479
includes taxes & fees
27 Oct - 28 Oct
Mid-Century Ranch * One-Level Living * Quiet Garden
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

3. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (316 reviews)
"Everything was great"
United States
Danielle
The price is £106
includes taxes & fees
12 Oct - 13 Oct
Starlite Motel
A natural setting with a stream, red chairs, and a forested area.

4. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is £260
includes taxes & fees
4 Nov - 5 Nov
Streamside Cottage Half Mile to Town of Woodstock
A wooden vanity with a mirror, two pendant lights, and a folded towel.

5. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Stone Ridge
9.4 out of 10, Exceptional, (30 reviews)
"Great location close to town. Cute and clean. Great little spot."
United States
Stephen
The price is £129
includes taxes & fees
28 Oct - 29 Oct
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

6. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (5 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is £193
includes taxes & fees
28 Oct - 29 Oct
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is £205
includes taxes & fees
15 Oct - 16 Oct
Gatherwild Ranch
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

8. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (45 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is £156
includes taxes & fees
5 Nov - 6 Nov
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

9. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is £219
includes taxes & fees
3 Nov - 4 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

10. The Loft At The Inn At High Falls

The Loft At The Inn At High Falls
High Falls
8.8 out of 10, Excellent, (24 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
The price is £265
includes taxes & fees
14 Oct - 15 Oct
The Loft At The Inn At High Falls
A cozy living room with a stone fireplace, a sofa, and a coffee table.

11. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is £207
includes taxes & fees
20 Oct - 21 Oct
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

12. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is £203
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

13. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (37 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is £240
includes taxes & fees
3 Nov - 4 Nov
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

14. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
The price is £206
includes taxes & fees
28 Oct - 29 Oct
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

15. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country!
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Very nice property that met our needs perfectly. Clean and very well maintained rooms. Lots of wildlife, beautiful wooded area. Peter, the host, was lovely and helpful."
United States
Barbara A.
The price is £365
includes taxes & fees
14 Oct - 15 Oct
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A rustic cabin with a wooden barrel entrance, stone fire pit, and outdoor seating area surrounded by a forest.

16. 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, (27 reviews)
"Perfect for a short get away"
United States
Darryl
The price is £243
includes taxes & fees
7 Oct - 8 Oct
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
A wooden cabin with a deck, a hot tub, and a chimney.

17. Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake

Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
East Jewett
10.0 out of 10, Exceptional, (16 reviews)
"The space was exactly as it is pictured. We really enjoyed our time. The host was extremely responsive."
United States
Jennifer C.
The price is £477
includes taxes & fees
29 Oct - 30 Oct
Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
Private kitchen

18. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (13 reviews)
"The Woods Cabin was exactly what it said it was; a teeny tiny, relatively new cabin pretty deep in the scrubby woods of rural NY. It was clean and fully functional, but it was very basic—it was much more than a tent, but the experience was not at all “glamping.” The owner was exceptionally responsive and helpful…no complaints there, or anywhere! As I said, the Woods Cabin is/was exactly what it said it was. Nothing more; nothing less."
United States
Nora Tracy
The price is £156
includes taxes & fees
21 Oct - 22 Oct
Woods Cabin-Kingston/Woodstock, NY.
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

19. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is £207
includes taxes & fees
8 Oct - 9 Oct
Stunning and Cozy loft apartment in kingston .
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

20. Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
The price is £419
includes taxes & fees
29 Oct - 30 Oct
Hot Tub - Hammock- Games - Grill - Large Colonial
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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"Clean and nicely smelling place. Good breakfast. Friendly staff."
Alexander 1-night trip
Posted 15 hours ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Town of Olive

Holiday Apartments in Town of Olive

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