Town of Olive Vacation Rentals

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Top cities in Town of Olive

Vacation Rentals

Shokan

Shokan

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Town of Olive vacation 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, (40 reviews)
"Clean and beautifully decorated room. Very comfortable, excellent bed and linens. Friendly and knowledgeable staff. An "out of the way " place and that's its charm, yet close enough - short car rides- to restaurants and other attractions. We'd gladly return!"
United States
Ronald
The price is CA $196
CA $288 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $182
CA $826 total
includes taxes & fees
Nov 9 - Nov 10
Mid-Century Ranch, One-Level Living, Quiet Garden
A wooden vanity with a mirror, two pendant lights, and a folded towel.

3. 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, (31 reviews)
"Absolutely beautiful place. Carefully prepared for our arrival with tea light and lampshades on throughout the accommodation. No complaints whatsoever and if anything exceeded our expectations. The location was great for our plans exploring Hudson Valley and surrounding areas. Would 100% recommend. Communication throughout was perfect 👌. Thank you for a wonderful stay ."
United Kingdom
Catherine
The price is CA $94
CA $190 total
includes taxes & fees
Dec 6 - Dec 7
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

4. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is CA $203
CA $227 total
includes taxes & fees
Nov 9 - Nov 10
Starlite Motel
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

5. 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, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is CA $171
CA $332 total
includes taxes & fees
Dec 1 - Dec 2
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

6. 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 CA $105
CA $340 total
includes taxes & fees
Nov 16 - Nov 17
Campfire Cottage: Fireplace, fire pit & no chores!
A natural setting with a stream, red chairs, and a forested area.

7. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (308 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 CA $200
CA $421 total
includes taxes & fees
Nov 10 - Nov 11
Streamside Cottage Half Mile to Town of Woodstock
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

8. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.2 out of 10, Very good, (47 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is CA $157
CA $359 total
includes taxes & fees
Nov 8 - Nov 9
The Studio at the Inn at High Falls
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.

9. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is CA $311
CA $380 total
includes taxes & fees
Nov 8 - Nov 9
Gatherwild Ranch
A cozy living room with a stone fireplace, a sofa, and a coffee table.

10. 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)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
The price is CA $137
CA $253 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

11. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is CA $105
CA $340 total
includes taxes & fees
Nov 9 - Nov 10
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

12. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.8 out of 10, Excellent, (19 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is CA $105
CA $201 total
includes taxes & fees
Dec 6 - Dec 7
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A wooden pergola with a bench underneath, surrounded by greenery and trees.

13. 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, (47 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is CA $194
CA $310 total
includes taxes & fees
Dec 2 - Dec 3
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A campfire surrounded by rocks in a grassy field with trees and hills in the background.

14. Cold Spring Lodge - Cabin 2

Cold Spring Lodge - Cabin 2
Big Indian
9.6 out of 10, Exceptional, (7 reviews)
"Location !"
United States
Bhavinkumar
The price is CA $154
CA $294 total
includes taxes & fees
Nov 9 - Nov 10
Cold Spring Lodge - Cabin 2
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

15. 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 CA $165
CA $266 total
includes taxes & fees
Nov 6 - Nov 7
Jessie's Harvest House
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

16. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $101
CA $186 total
includes taxes & fees
Nov 9 - Nov 10
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Private kitchen

17. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (17 reviews)
"We loved the little cabin in the woods!"
United States
Patti G.
The price is CA $173
CA $282 total
includes taxes & fees
Nov 10 - Nov 11
Woods Cabin-Kingston/Woodstock, NY.
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

18. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is CA $120
CA $401 total
includes taxes & fees
Nov 16 - Nov 17
Retro Retreat: renovated 2BR, desk, no chore list!
A modern kitchen with white cabinets, a central island, and a view to the outside.

19. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is CA $160
CA $280 total
includes taxes & fees
Nov 10 - Nov 11
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

20. 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, (39 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is CA $142
CA $341 total
includes taxes & fees
Nov 9 - Nov 10
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine

10/10 Excellent

Parfait pour une pause lors de trajet en voiture. Propre, accueillant , confortable. Personnel courtois et attenionné.
Canada
Martin
Reviewed November 5, 2026
Holiday Inn Express & Suites Kingston-Ulster by IHG

Find out more about Town of Olive

Everything you need to know about Town of Olive vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Olive vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Olive vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Town of Olive vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Olive. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Olive vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Olive vacation rentals we have selected for you start as low as CA $93 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Olive rentals

At Expedia, we put the best Town of Olive vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Town of Olive rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Olive vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Olive. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.