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

Olivebridge Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Olivebridge vacation rentals

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

1. NEW: Atomic Ranch - MCM One Level in Olivebridge

NEW: Atomic Ranch - MCM One Level in Olivebridge
Olivebridge
$529 nightly
The price is $597
Sep 15 - Sep 16
Total with taxes and fees
NEW: Atomic Ranch - MCM One Level in Olivebridge
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
10.0 out of 10, Exceptional, (31 reviews)
"I enjoyed my stay at this lovely, clean, cozy home."
United States
Taela
$177 nightly
The price is $198
Sep 9 - Sep 10
Total with taxes and fees
West Wing - a unique private space w/patio
A wooden vanity with a mirror, two pendant lights, and a folded towel.

3. 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
$135 nightly
The price is $138
Sep 7 - Sep 8
Total with taxes and fees
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A kitchen with wooden countertops, a dining table, and chairs. There are jars and cups on the counter.

4. 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, (3 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
$209 nightly
The price is $212
Sep 7 - Sep 8
Total with taxes and fees
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A wooden deck with two green lounge chairs and a covered area.

5. Charming & Cozy Cabin w/ Screened Porch

Charming & Cozy Cabin w/ Screened Porch
Stone Ridge
9.0 out of 10, Wonderful, (4 reviews)
"Freezing temperatures and a ton of snow made for a winter wonderland. Had a phenomenon 5 days with family by reading books by the fireplace. Three thumbs up!"
United States
Michael G.
$522 nightly
The price is $584
Sep 16 - Sep 17
Total with taxes and fees
Charming & Cozy Cabin w/ Screened Porch
A natural setting with a stream, red chairs, and a forested area.

6. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (296 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveler
$272 nightly
The price is $305
Sep 7 - Sep 8
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
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.

7. 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, (42 reviews)
"The pictures are misleading"
United States
Jia
$241 nightly
The price is $269
Sep 13 - Sep 14
Total with taxes and fees
The Studio at the Inn at High Falls
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

8. 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
8.6 out of 10, Excellent, (18 reviews)
"Clean cozy will be staying again"
United States
Michael C.
$135 nightly
The price is $138
Sep 7 - Sep 8
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

9. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.4 out of 10, Exceptional, (10 reviews)
$180 nightly
The price is $202
Sep 3 - Sep 4
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A cozy living room with a stone fireplace, a sofa, and a coffee table.

10. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (16 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
$203 nightly
The price is $206
Sep 9 - Sep 10
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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, (22 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
$485 nightly
The price is $543
Sep 8 - Sep 9
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

12. 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.
$220 nightly
The price is $246
Sep 8 - Sep 9
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
An open deck with potted plants, a table, and a chair.

13. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$277 nightly
The price is $310
Sep 8 - Sep 9
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
A forest campsite with a tent, a fire pit, and a bench.

14. 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.
$136 nightly
The price is $152
Sep 3 - Sep 4
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park
A log cabin interior with a large gray sectional sofa, a wooden coffee table, and a dining area with a kitchen in the background.

15. Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Boiceville
9.8 out of 10, Exceptional, (11 reviews)
"Great place and very clean. Beds are very comfortable. Would definitely stay here again."
United States
Charles S.
$536 nightly
The price is $600
Sep 3 - Sep 4
Total with taxes and fees
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

16. 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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
$218 nightly
The price is $244
Sep 3 - Sep 4
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

17. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
$239 nightly
The price is $268
Sep 23 - Sep 24
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

18. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.2 out of 10, Wonderful, (35 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$251 nightly
The price is $281
Sep 17 - Sep 18
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

19. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (312 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 3 - Sep 4
Total with taxes and fees
Starlite Motel
A kitchen with a wooden countertop, a stove, and a dining area with two chairs and a table.

20. Kitty Kabana Tiny House

Kitty Kabana Tiny House
Grahamsville
9.2 out of 10, Wonderful, (5 reviews)
"Very clean and cozy property with gracious host."
United States
Maxine
$247 nightly
The price is $278
Sep 3 - Sep 4
Total with taxes and fees
Kitty Kabana Tiny House
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"Clean room. Could use some updating . Smelled musty. Sherry in a decanter was a nice touch after stumbling through dark parking lot to find an overgrown walkway. Best part was the town .. adorable ! Lined with cute boutiques and all types of places to eat Def had quite a historic vibe. The overall area is stunning and quite picturesque.!"
Lori 2-night trip
Posted 9 hours ago
Beekman Arms and Delamater Inn

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?

The Chicken Coop: Visitors like this Olivebridge vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.