Olivebridge Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Olivebridge vacation 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 CA $184
CA $838 total
includes taxes & fees
Nov 15 - Nov 16
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, (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 CA $199
CA $292 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $72
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $72
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $124
CA $283 total
includes taxes & fees
Dec 1 - Dec 2
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
8.2 out of 10, Very good, (47 reviews)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
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, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveller
The price is CA $203
CA $424 total
includes taxes & fees
Nov 15 - Nov 16
Streamside Cottage Half Mile to Town of Woodstock
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

8. 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 CA $106
CA $329 total
includes taxes & fees
Nov 16 - Nov 17
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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, (51 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is CA $361
CA $827 total
includes taxes & fees
Nov 15 - Nov 16
Woodstock Historic Artist Estate - The Carriage House
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

10. 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 CA $206
CA $230 total
includes taxes & fees
Nov 16 - Nov 17
Starlite Motel
A modern living room with a large window, a fireplace, and a cozy seating area.

11. Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (25 reviews)
"Very cute place, beautiful area. Would absolutely choose again!"
United States
Michael S.
The price is CA $286
CA $632 total
includes taxes & fees
Nov 17 - Nov 18
Mossy Moody Cabin in High Falls, NY
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 CA $106
CA $329 total
includes taxes & fees
Nov 16 - Nov 17
Campfire Cottage: Fireplace, fire pit & no chores!
A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

13. 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 CA $284
CA $454 total
includes taxes & fees
Nov 15 - Nov 16
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Private kitchen

14. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (18 reviews)
"We loved the little cabin in the woods!"
United States
Patti G.
The price is CA $175
CA $287 total
includes taxes & fees
Nov 15 - Nov 16
Woods Cabin-Kingston/Woodstock, NY.
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.

15. 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 unit was immaculately clean and everything was provided. Beds were comfortable and the ac units made it very comfortable for sleeping. Really enjoyed playing the msPacman/Galaga game on the wall in the living room. lol we didn’t have time to enjoy the yard or hot tub but it was nice to have those amenities if we wanted to."
United States
Erick and Lana S.
The price is CA $167
CA $366 total
includes taxes & fees
Dec 1 - Dec 2
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A narrow pathway leading to a row of colorful mobile homes, each with a distinct number and nameplate.

16. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Great location, had everything needed for a comfortable stay."
United States
Michael W.
The price is CA $88
CA $319 total
includes taxes & fees
Dec 9 - Dec 10
Butterfly Bungalow Studio · Saugerties/Woodstock
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

17. 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 CA $109
CA $391 total
includes taxes & fees
Nov 18 - Nov 19
Retro Retreat: renovated 2BR, desk, no chore list!
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

18. 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 CA $368
CA $703 total
includes taxes & fees
Nov 15 - Nov 16
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

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 CA $135
CA $340 total
includes taxes & fees
Nov 29 - Nov 30
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

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 CA $169
CA $359 total
includes taxes & fees
Nov 16 - Nov 17
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.
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Top Olivebridge Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
Lake Katrine

10/10 Excellent

Parfait pour une pause lors de trajet en voiture. Propre, accueillant , confortable. Personnel courtois et attenionné.
Canada
Martin
Reviewed November 5, 2026
Holiday Inn Express & Suites Kingston-Ulster by IHG

Find out more about Olivebridge

Everything you need to know about Olivebridge vacation rentals

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

Olivebridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Olivebridge. 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 Olivebridge vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Olivebridge vacation rentals we have selected for you start as low as CA $72 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Olivebridge rentals

At Expedia, we put the best Olivebridge vacation 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 Olivebridge 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 Olivebridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Olivebridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Olivebridge?

Yes, we offer vacation rentals close to well known points of interest in Olivebridge, or you can select a secluded option if you're looking for relaxation. 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's the top vacation rental that Olivebridge has to offer?

High Point Mtn House ~ Celebrate Summer ~ Privacy ~ SERENITY NOW~ Gorgeous VIEWS: This highly rated vacation home rental in Olivebridge is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Olivebridge?

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

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 larger area.

What are vacation rentals like in Olivebridge?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Olivebridge. Vacation rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.