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

Olivebridge Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$571 nightly
The price is $645
Oct 27 - Oct 28
Total with taxes and fees
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, (36 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
$177 nightly
The price is $198
Oct 5 - Oct 6
Total with taxes and fees
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.
$145 nightly
The price is $148
Oct 4 - Oct 5
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

4. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (315 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Oct 5 - Oct 6
Total with taxes and fees
Starlite Motel
A natural setting with a stream, red chairs, and a forested area.

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 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.
$313 nightly
The price is $351
Oct 20 - Oct 21
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

6. 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, (5 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
$255 nightly
The price is $259
Oct 28 - Oct 29
Total with taxes and fees
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A wooden vanity with a mirror, two pendant lights, and a folded towel.

7. 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, (30 reviews)
"Great location close to town. Cute and clean. Great little spot."
United States
Stephen
$160 nightly
The price is $162
Nov 3 - Nov 4
Total with taxes and fees
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A spacious living room with a fireplace, comfortable seating, and a dining area with a wooden table.

8. LONGVIEW FARM - Reimagined Modern Farmhouse

LONGVIEW FARM - Reimagined Modern Farmhouse
Marbletown
$1,909 nightly
The price is $1,966
Oct 5 - Oct 6
Total with taxes and fees
LONGVIEW FARM - Reimagined Modern Farmhouse
A spacious living room with a high ceiling, skylights, a dining area with a wooden table and chairs, a fireplace, and a television.

9. NEW RENO, HIGH FALLS, near Mohonk preserve, New Paltz, Kingston

NEW RENO, HIGH FALLS, near Mohonk preserve, New Paltz, Kingston
High Falls
10.0 out of 10, Exceptional, (159 reviews)
"Everything was remodeled so it was great. The basement with the ping-pong table was a lot of fun."
United States
Jennifer M.
$718 nightly
The price is $804
Oct 17 - Oct 18
Total with taxes and fees
NEW RENO, HIGH FALLS, near Mohonk preserve, New Paltz, Kingston
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

10. 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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
$240 nightly
The price is $269
Oct 20 - Oct 21
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a central island, black cabinetry, and pendant lighting.

11. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
$577 nightly
The price is $646
Oct 5 - Oct 6
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
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.

12. 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)
"The pictures are misleading"
United States
Jia
$242 nightly
The price is $270
Oct 4 - Oct 5
Total with taxes and fees
The Studio at the Inn at High Falls
A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

13. The Loft At The Inn At High Falls

The Loft At The Inn At High Falls
High Falls
9.0 out of 10, Wonderful, (23 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
$316 nightly
The price is $354
Oct 5 - Oct 6
Total with taxes and fees
The Loft At The Inn At High Falls
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

14. Cozy Mid-Century Retreat with Spa Hot Tub

Cozy Mid-Century Retreat with Spa Hot Tub
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"Great spot, close to town but removed enough to have total privacy. Thank you!"
United States
Alec M.
$674 nightly
The price is $755
Oct 7 - Oct 8
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
A modern living room with a large window, a fireplace, and a cozy seating area.

15. Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (24 reviews)
"My husband and I had a lovely stay at the Mossy Moody Cabin. Mackenzie was a great host, easy to communicate with, and the cabin had everything we needed. The hot tub was such a nice feature too. It was close to town but nice and private- we loved it!"
United States
Jennifer M.
$431 nightly
The price is $483
Oct 8 - Oct 9
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
A modern outdoor deck with a sectional sofa, a glass door leading to a red chair, and a white fence.

16. Brand New House with Huge Patio

Brand New House with Huge Patio
Kerhonkson
8.8 out of 10, Excellent, (6 reviews)
"This place was perfect for our weekend getaway."
United States
Soonmi
$736 nightly
The price is $824
Oct 9 - Oct 10
Total with taxes and fees
Brand New House with Huge Patio
Private kitchen

17. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (12 reviews)
"Oh, I gave this property excellent scores for all the questions but I am reminded now by the suggestions for what to write about about the fact that it listed an Ocean view, which is obviously a mistake. It’s nowhere near the ocean. There’s no ocean view. It is in the woods it’s secluded.I actually took a very little walk in the middle of the night in the dark using my cell phone flashlight and got kind of lost for a while, but managed to find my way back. That was quite an interesting...
United States
Michael H.
$180 nightly
The price is $202
Oct 5 - Oct 6
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

18. 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.
$243 nightly
The price is $275
Oct 6 - Oct 7
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

19. 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.
$260 nightly
The price is $291
Oct 12 - Oct 13
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

20. 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, (6 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.
$223 nightly
The price is $250
Nov 1 - Nov 2
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Olivebridge Hotel Reviews

AutoCamp Catskills

AutoCamp Catskills

10/10 Excellent
"Absolutely loved our stay! The area is beautiful, the property is amazing and so well-maintained, and the friendly staff. This was our first time staying in a premium Airstream for both me and my hubby, and we were honestly amazed very clean too! Such a fun, unique, and awesome experience."
Michelle 1-night trip
Posted 9 hours ago
AutoCamp Catskills

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Olivebridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.