A mountainous landscape with autumn foliage.

Town of Olive Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Town of Olive holiday rentals

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 AU$293
includes taxes & fees
10 Nov - 11 Nov
West Wing - a unique private space w/patio

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

Mid-Century Ranch, One-Level Living, Quiet Garden
Olivebridge
The price is AU$831
includes taxes & fees
10 Nov - 11 Nov
Mid-Century Ranch, One-Level Living, Quiet Garden

3. 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 AU$237
includes taxes & fees
10 Nov - 11 Nov
Starlite Motel

4. 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 AU$199
includes taxes & fees
30 Nov - 1 Dec
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

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 AU$316
includes taxes & fees
1 Dec - 2 Dec
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

6. 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 AU$371
includes taxes & fees
10 Nov - 11 Nov
The Studio at the Inn at High Falls

7. 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 AU$355
includes taxes & fees
17 Nov - 18 Nov
Campfire Cottage: Fireplace, fire pit & no chores!

8. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveller
The price is AU$421
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock

9. 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 AU$325
includes taxes & fees
25 Nov - 26 Nov
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

10. 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 AU$349
includes taxes & fees
12 Nov - 13 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

11. 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 AU$189
includes taxes & fees
12 Nov - 13 Nov
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

12. 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 AU$269
includes taxes & fees
10 Nov - 11 Nov
Jessie's Harvest House

13. 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 AU$301
includes taxes & fees
10 Nov - 11 Nov
Woods Cabin-Kingston/Woodstock, NY.

14. 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, (48 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is AU$327
includes taxes & fees
9 Dec - 10 Dec
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

15. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
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 AU$182
includes taxes & fees
10 Nov - 11 Nov
A Cozy Private Suite in a Country Home near New Paltz

16. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
10.0 out of 10, Exceptional, (1 review)
"Amazing sauna session"
United States
AYANO
The price is AU$396
includes taxes & fees
10 Nov - 11 Nov
Gatherwild Ranch

17. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is AU$273
includes taxes & fees
22 Nov - 23 Nov
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

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 AU$417
includes taxes & fees
18 Nov - 19 Nov
Retro Retreat: renovated 2BR, desk, no chore list!

19. 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 AU$393
includes taxes & fees
16 Nov - 17 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

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 AU$341
includes taxes & fees
16 Nov - 17 Nov
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Town of Olive Hotel Reviews

Find out more about Town of Olive

Everything you need to know about Town of Olive holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Olive holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Olive holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Olive holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Olive holiday rentals we have chosen for you start as low as AU$237 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 holiday 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 holiday.

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.