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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$502 nightly
The price is $567
Sep 29 - Sep 30
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
8.6 out of 10, Excellent, (18 reviews)
"Clean cozy will be staying again"
United States
Michael C.
$129 nightly
The price is $131
Sep 28 - Sep 29
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

4. 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.
$236 nightly
The price is $264
Sep 27 - Sep 28
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

5. 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.
$237 nightly
The price is $265
Sep 28 - Sep 29
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
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)
"The pictures are misleading"
United States
Jia
$242 nightly
The price is $270
Sep 27 - Sep 28
Total with taxes and fees
The Studio at the Inn at High Falls
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

7. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 24 - Sep 25
Total with taxes and fees
Starlite Motel
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

8. 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
$189 nightly
The price is $192
Sep 28 - Sep 29
Total with taxes and fees
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A natural setting with a stream, red chairs, and a forested area.

9. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (299 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.
$280 nightly
The price is $314
Sep 27 - Sep 28
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A wooden vanity with a mirror, two pendant lights, and a folded towel.

10. 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
$137 nightly
The price is $139
Sep 29 - Sep 30
Total with taxes and fees
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

11. 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, (101 reviews)
"Wonderful stay. "
United States
Chris L.
$233 nightly
The price is $261
Sep 24 - Sep 25
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
An open deck with potted plants, a table, and a chair.

12. 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 24 - Sep 25
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

13. 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, (37 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$271 nightly
The price is $304
Oct 7 - Oct 8
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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
Sep 24 - Sep 25
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
A forest campsite with a tent, a fire pit, and a bench.

15. 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 24 - Sep 25
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park

16. 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.
$181 nightly
The price is $203
Sep 29 - Sep 30
Total with taxes and fees
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.

17. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (32 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
$255 nightly
The price is $286
Sep 30 - Oct 1
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

18. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$123 nightly
The price is $138
Sep 29 - Sep 30
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A wooden cabin with a metal roof, surrounded by tall trees and a hammock.

19. Tiny Cat Tiny House

Tiny Cat Tiny House
Grahamsville
9.0 out of 10, Wonderful, (13 reviews)
"Very cute house with the necessities and more!"
United States
TAYLOR L.
$213 nightly
The price is $239
Sep 24 - Sep 25
Total with taxes and fees
Tiny Cat Tiny House
A rustic cabin with a wooden deck and a chair, surrounded by dense forest.

20. '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
8.0 out of 10, Very good, (51 reviews)
"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.
$133 nightly
The price is $148
Sep 27 - Sep 28
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, 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

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

8/10 Good
"There are no in room safes"
Jean 2-night trip
Posted 5 hours ago
Residence Inn by Marriott Kingston

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.