Olivebridge Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Olivebridge holiday rentals

Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is HK$1,237
HK$2,623 total
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock
Exterior
Starlite Motel

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (273)
"Awesome place to stay!"
United States
Earl
The price is HK$961
HK$1,076 total
includes taxes & fees
5 Jan - 6 Jan 2026
Starlite Motel
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (62)
"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. "
United States
Rebecca
The price is HK$1,156
HK$1,835 total
includes taxes & fees
7 Jan - 8 Jan 2026
Esopus Creek modern Tiny house Retreat!
Exterior
The Farm at Hyde Park

The Farm at Hyde Park

The Farm at Hyde Park
Staatsburg
9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park
Smart TV, fireplace, ping pong, video library
Stunning Catskills Cabin Getaway, facing BelleAyre

Stunning Catskills Cabin Getaway, facing BelleAyre

Stunning Catskills Cabin Getaway, facing BelleAyre
Fleischmanns
10.0 out of 10, Exceptional, (131)
"Absolutely fabulous place we stayed for my daughter’s wedding. "
United States
Robert Joseph J.
Stunning Catskills Cabin Getaway, facing BelleAyre
Smart TV, fireplace, DVD player, table football
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
West Kill
9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.2 out of 10, Very good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is HK$973
HK$1,264 total
includes taxes & fees
14 Dec - 15 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Bearsville
10.0 out of 10, Exceptional, (124)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.
West Shokan
10.0 out of 10, Exceptional, (54)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Children’s area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is HK$1,401
HK$2,406 total
includes taxes & fees
14 Dec - 15 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

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

A Spectacular 50 Mile View of the Hudson Valley in all seasons
Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties
Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Hunter
10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
The price is HK$3,198
HK$7,689 total
includes taxes & fees
15 Dec - 16 Dec
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is HK$630
HK$1,769 total
includes taxes & fees
11 Dec - 12 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$959
HK$1,719 total
includes taxes & fees
20 Dec - 21 Dec
TRANQUIL MOUNTAIN SOLITUDE
Exterior
Beautiful new house 3/4 mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain
hunter
9.6 out of 10, Exceptional, (138)
"Really beautiful location with plenty of bedrooms. Very clean!"
United States
Ellen B.
Beautiful new house 3/4 mile from Hunter Mountain
Dining
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Grahamsville
9.4 out of 10, Exceptional, (36)
"Very well stocked. Beautiful, quiet location. Very comfortable. "
United States
Ladytiger
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is HK$869
HK$1,529 total
includes taxes & fees
13 Dec - 14 Dec
Mid-Century DJ’s Dream
Terrace/patio
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (11)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY
Saugerties
9.0 out of 10, Wonderful, (13)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Cute lodge near Hunter Mountain. Totally recommend!"
Melisa 1-night trip
Posted 2 days ago
Hunter Lodge, a Bluebird by Lark

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?

The Farm at Hyde Park: This holiday home rental outside of Olivebridge is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 13 Expedia holiday rentals in Olivebridge for a memorable holiday.

What can I see and do in Olivebridge?

Esopus Creek and Catskill Mountains are a couple of lovely local spots to get outside and enjoy nature. While here, Catskill State Park and Brown's Station are other places worth a visit.

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.