Town of Olive Holiday Rentals

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Top Holiday Rentals Destinations in Town of Olive

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
The price is NZ$311
includes taxes & fees
19 Nov - 20 Nov
West Wing - a unique private space w/patio

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

Olivebridge
10.0 out of 10, Exceptional, (1)
The price is NZ$1,063
includes taxes & fees
17 Nov - 18 Nov
Atomic Ranch - MCM One Level in Olivebridge. Great Outdoor Space!

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.
The price is NZ$938
includes taxes & fees
16 Nov - 17 Nov
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Starlite Motel

2.5 star property
Big Indian
9.2 out of 10, Wonderful, (272)
"Awesome place to stay!"
United States
Earl
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Starlite Motel

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is NZ$442
includes taxes & fees
10 Dec - 11 Dec
Campfire Cottage: Fireplace, fire pit & no chores!

Peaceful Cabin w/ Fire Pit & Creek Access

Saugerties
10.0 out of 10, Exceptional, (13)
"Great little space , clean, comfortable and equipped with everything I needed for a nice weekend! Would stay again if ever I return to the area ."
United States
Leah G.
The price is NZ$537
includes taxes & fees
11 Dec - 12 Dec
Peaceful Cabin w/ Fire Pit & Creek Access

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

Kingston
9.6 out of 10, Exceptional, (14)
"We stayed for a week. The first several days just me and my daughter and then my husband joined us. I was able to work remotely and there was a nice desk with a screen, keyboard and mouse provided. The place is decorated in a very cool way, absolutely loved it. Host was great to communicate with and made sure we were comfortable. Left us some pancake mix and a waffle maker which we enjoyed very much!"
United States
Jessica V.
The price is NZ$505
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: renovated 2BR, desk, no chore list!

Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown
10.0 out of 10, Exceptional, (4)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is NZ$380
includes taxes & fees
20 Nov - 21 Nov
Charming loft cottage in tranquil Germantown with WiFi, AC

Modern Hudson Valley Retreat Near Mohonk

2.0 star property
Plattekill
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
The price is NZ$461
includes taxes & fees
17 Nov - 18 Nov
Modern Hudson Valley Retreat Near Mohonk

Romantic Apartment in Historic Stone Ridge

Stone Ridge
9.4 out of 10, Exceptional, (18)
"Grear"
United States
Gretka D.
The price is NZ$286
includes taxes & fees
1 Dec - 2 Dec
Romantic Apartment in Historic Stone Ridge

Country Cottage with beautiful views and easy access to Catskills activities.

Saugerties
10.0 out of 10, Exceptional, (12)
"Cozy little spot for a quick getaway. Very clean, quiet location. Easy check-in. "
United States
Mariclare C.
The price is NZ$313
includes taxes & fees
17 Nov - 18 Nov
Country Cottage with beautiful views and easy access to Catskills activities.

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is NZ$256
includes taxes & fees
17 Nov - 18 Nov
Sioux Tipi on Chloe's Lake

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveller
The price is NZ$344
includes taxes & fees
18 Nov - 19 Nov
Mid-Century DJ’s Dream

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7)
"Absolutely worth it, this place is a great getaway in a dreamy spot in the woods, with everything you need to relax. Don’t forget to turn on the heated floors and hook up your tunes to the bathroom Bluetooth speaker. Thanks for a wonderful experience! "
United States
Samantha
The price is NZ$490
includes taxes & fees
17 Nov - 18 Nov
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Phoenicia
10.0 out of 10, Exceptional, (22)
"cute fun place. loved the hot tub "
United States
Joey C.
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

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

Kerhonkson
9.4 out of 10, Exceptional, (12)
"The Dream Cottage at the Gunks is a perfect place for a cozy stay in a scenic location. Everything was very clean and decorated with good taste. Although we were not there much due to how much we did over the weekend, our time there was very pleasant. I highly recommend staying at this property."
United States
kim h.
The price is NZ$384
includes taxes & fees
18 Nov - 19 Nov
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

The Innwoods - Studio Apartment 2

Tannersville
10.0 out of 10, Exceptional, (3)
"This was beautiful! I've found my own personal writer's retreat. The excellent use of space made it feel as if "I already lived there". It was expertly designed. The soft carpet leading up to the apartment. Great appliances. Cozy lighting. Comfortable bed. Surprisingly spacious bathroom. Soft towels. The location - insanely perfect. A few doors down or across the street from great restaurants, cafes, shops... and close to where the weekend Tannersville Trolley stops... so you can get a ride to...
United States
Zoe M.
The price is NZ$304
includes taxes & fees
18 Nov - 19 Nov
The Innwoods - Studio Apartment 2

Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson
8.8 out of 10, Excellent, (3)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is NZ$267
includes taxes & fees
17 Nov - 18 Nov
Glamping Tent & Campsite by Minnewaska State Park

Private Studio Close to Downtown Rhinebeck

RHINEBECK
10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is NZ$425
includes taxes & fees
17 Nov - 18 Nov
Private Studio Close to Downtown Rhinebeck

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Kingston
9.4 out of 10, Exceptional, (22)
"We came down with our dog. We work a lot and needed a break. The place is cozy and comfy and the outdoor space is so lovely. Good mix of sunny space and shaded space.Our dog very much enjoyed the backyard and we loved the small businesses within walking distance "
United States
Heather H.
The price is NZ$410
includes taxes & fees
18 Nov - 19 Nov
Hot Tub - Fire Pit - BBQ - Hammock - 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

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 favorite 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 depends 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 selected for you start as low as NZ$246 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.