A large lake with a bridge, surrounded by mountains and greenery.

Olivebridge Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Olivebridge holiday rentals

A living room with a sofa, television, and plants.

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

Mid-Century Ranch * One-Level Living * Quiet Garden
Olivebridge
The price is HK$1,035
HK$4,444 total
includes taxes & fees
26 Oct - 27 Oct
Mid-Century Ranch * One-Level Living * Quiet Garden
A wooden deck with a bench, surrounded by a forested area.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (39 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 HK$1,098
HK$1,722 total
includes taxes & fees
26 Oct - 27 Oct
West Wing - a unique private space w/patio
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

3. 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 HK$473
HK$1,080 total
includes taxes & fees
1 Nov - 2 Nov
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A wooden vanity with a mirror, two pendant lights, and a folded towel.

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 HK$525
HK$1,132 total
includes taxes & fees
1 Nov - 2 Nov
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.

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 HK$720
HK$1,693 total
includes taxes & fees
1 Nov - 2 Nov
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
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.

6. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is HK$882
HK$2,121 total
includes taxes & fees
26 Oct - 27 Oct
The Studio at the Inn at High Falls
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, (307 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 HK$1,122
HK$2,469 total
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock
Private kitchen

8. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (17 reviews)
"Thank you. What an experience!"
United States
Burc
The price is HK$894
HK$1,581 total
includes taxes & fees
10 Nov - 11 Nov
Woods Cabin-Kingston/Woodstock, NY.
A modern kitchen with a large island, a sink, and wooden stools.

9. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (50 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is HK$1,180
HK$3,483 total
includes taxes & fees
26 Oct - 27 Oct
Woodstock Historic Artist Estate - The Carriage House
A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

10. Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Woodstock
9.0 out of 10, Wonderful, (2 reviews)
"Great location."
United States
Louis
The price is HK$1,569
HK$2,644 total
includes taxes & fees
26 Oct - 27 Oct
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

11. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (320 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is HK$1,137
HK$1,274 total
includes taxes & fees
26 Oct - 27 Oct
Starlite Motel
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 HK$588
HK$1,985 total
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A forest campsite with a tent, a fire pit, and a bench.

13. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is HK$671
HK$1,190 total
includes taxes & fees
26 Oct - 27 Oct
Glamping Tent & Campsite by Minnewaska State Park
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

14. 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 HK$541
HK$1,924 total
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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 HK$1,882
HK$3,862 total
includes taxes & fees
23 Nov - 24 Nov
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A bedroom with a large bed, a TV mounted on the wall, a window with a view, and a painting on the wall.

16. 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 HK$925
HK$1,578 total
includes taxes & fees
29 Oct - 30 Oct
Jessie's Harvest House
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

17. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is HK$1,229
HK$1,957 total
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
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 HK$690
HK$2,363 total
includes taxes & fees
3 Nov - 4 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
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, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is HK$1,176
HK$2,082 total
includes taxes & fees
2 Nov - 3 Nov
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 - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is HK$1,044
HK$2,259 total
includes taxes & fees
3 Nov - 4 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 Olivebridge Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"Room was clean and staff was friendly and helpful!"
Haiwan 2-night trip
Posted less than an hour ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Olivebridge

Search for holiday rentals in Olivebridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Olivebridge using one of the methods below:

  • View our selection of featured holiday rentals in Olivebridge
  • Use the map to find apartments and other holiday homes in the Olivebridge neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Olivebridge while they last

Look no further and take a look at our great range of rental properties in Olivebridge!

Frequently asked questions

Can I find holiday rentals in Olivebridge?

Yes, there are holiday rentals close to the most popular sights in Olivebridge, or you can select a more secluded option if you're looking for a relaxing stay. Olivebridge is known for its ski areas and mountain views. Make sure you have time to check out the entertainment choices and restaurants during your trip.

What are some of the best holiday rentals that Olivebridge has to offer?

High Point Mtn House ~ Celebrate Summer ~ Privacy ~ SERENITY NOW~ Gorgeous VIEWS: This highly rated holiday home rental in Olivebridge is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Olivebridge?

Choose from 9 Expedia holiday rentals in Olivebridge for a memorable holiday.

What can I see and do in Olivebridge?

Esopus Creek and Brown's Station are a couple of lovely local spots to get outside and enjoy nature. Catskill State Park and Ashokan Rail Trail- Woodstock Dike Trailhead are a couple of places you'll find in the wider area.

What are holiday rentals like in Olivebridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Olivebridge. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.