Town of Olive Holiday Rentals

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Top Holiday Rentals Destinations in Town of Olive

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (268)
"The property was beautiful! Definitely coming back!"
The price is NZ$243
includes taxes & fees
30 Sept - 1 Oct
Starlite Motel

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is NZ$281
includes taxes & fees
1 Oct - 2 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Sioux Tipi on Chloe's Lake

9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is NZ$252
includes taxes & fees
5 Oct - 6 Oct
Sioux Tipi on Chloe's Lake

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is NZ$543
includes taxes & fees
5 Oct - 6 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (92)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (56)
"We really loved our stay and the wonderful host miss rosanna was very very nice kind and helpful god bless this lady need more like her in the world..."
The price is NZ$448
includes taxes & fees
30 Sept - 1 Oct
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Tiny Cat Tiny House

10.0 out of 10, Exceptional, (4)
"An ideal place to forget about the city, perfect for a long weekend"
The price is NZ$407
includes taxes & fees
30 Sept - 1 Oct
Tiny Cat Tiny House

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is NZ$873
includes taxes & fees
30 Sept - 1 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Jessie's Harvest House

10.0 out of 10, Exceptional, (2)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is NZ$328
includes taxes & fees
30 Sept - 1 Oct
Jessie's Harvest House

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is NZ$418
includes taxes & fees
1 Oct - 2 Oct
Esopus Creek modern Tiny house Retreat!

The Farm at Hyde Park

9.8 out of 10, Exceptional, (79)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park

Sexiest Lil Cabin in Saugerties, NY

9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is NZ$257
includes taxes & fees
30 Sept - 1 Oct
Sexiest Lil Cabin in Saugerties, NY

Stunning Catskills Cabin Getaway, facing BelleAyre

9.8 out of 10, Exceptional, (127)
"Great property for a ski trip to Belleayre. Close to the mountain. "
Stunning Catskills Cabin Getaway, facing BelleAyre

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

10.0 out of 10, Exceptional, (228)
"Super comfy house on the water with great local fishing opportunities! "
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

8.2 out of 10, Very good, (63)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

9.8 out of 10, Exceptional, (82)
"Lovely cozy spot with plenty to do inside and out. "
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

10.0 out of 10, Exceptional, (17)
"House was great, hosts were very accommodating. Location was perfect to get to Belleayre Mountain. "
The price is NZ$1,450
includes taxes & fees
30 Sept - 1 Oct
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is NZ$395
includes taxes & fees
30 Sept - 1 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
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

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$243 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.