Olivebridge Vacation Rentals from $140: Search Short-Term Rentals

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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

Olivebridge

$547 nightly

Oct 27 - Oct 28

Total with taxes and fees

A wooden deck with a bench, surrounded by a forested area.

2. West Wing - a unique private space w/patio

Shokan

MIKE W.

$178 nightly

Oct 12 - Oct 13

Total with taxes and fees

A wooden vanity with a mirror, two pendant lights, and a folded towel.

3. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Stone Ridge

Stephen

$164 nightly

Oct 28 - Oct 29

Total with taxes and fees

A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

4. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Stone Ridge

Michael C.

$159 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

Stone Ridge

Tarun

$248 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

High Falls

Jia

$240 nightly

Oct 7 - Oct 8

Total with taxes and fees

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

Big Indian

Danielle

$125 nightly

Oct 12 - Oct 13

Total with taxes and fees

A natural setting with a stream, red chairs, and a forested area.

8. Streamside Cottage Half Mile to Town of Woodstock

Woodstock

Kristen S.

$303 nightly

Nov 4 - Nov 5

Total with taxes and fees

9. Woods Cabin-Kingston/Woodstock, NY.

Kingston

"The Woods Cabin was exactly what it said it was; a teeny tiny, relatively new cabin pretty deep in the scrubby woods of rural NY. It was clean and fully functional, but it was very basic—it was much more than a tent, but the experience was not at all “glamping.” The owner was exceptionally responsive and helpful…no complaints there, or anywhere! As I said, the Woods Cabin is/was exactly what it said it was. Nothing more; nothing less."

Nora Tracy

$180 nightly

Oct 7 - Oct 8

Total with taxes and fees

A modern living room with a large window, a fireplace, and a cozy seating area.

10. Mossy Moody Cabin in High Falls, NY

High Falls

Jennifer M.

$395 nightly

Oct 7 - Oct 8

Total with taxes and fees

A spacious living room with a fireplace, comfortable seating, and a dining area with a wooden table.

11. LONGVIEW FARM - Reimagined Modern Farmhouse

Marbletown

$1,957 nightly

Oct 7 - Oct 8

Total with taxes and fees

A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

12. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

Woodstock

Barbara A.

$440 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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

Kingston

Jim R.

$239 nightly

Nov 3 - Nov 4

Total with taxes and fees

A compact kitchen with blue cabinets, a white stove, and yellow chairs.

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston

Brendan B.

$221 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

Kingston

Clara L.

$247 nightly

Oct 28 - Oct 29

Total with taxes and fees

A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

16. Retro Retreat: renovated 2BR, desk, no chore list!

Kingston

Kelley Marie

$277 nightly

Nov 2 - Nov 3

Total with taxes and fees

A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

17. The Loft At The Inn At High Falls

High Falls

Inez

$316 nightly

Oct 8 - Oct 9

Total with taxes and fees

A forest campsite with a tent, a fire pit, and a bench.

18. Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

Andie C.

$136 nightly

Oct 7 - Oct 8

Total with taxes and fees

An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

19. Cozy Mid-Century Retreat with Spa Hot Tub

Woodstock

Alec M.

A modern outdoor deck with a sectional sofa, a glass door leading to a red chair, and a white fence.

20. Brand New House with Huge Patio

Kerhonkson

Soonmi

$736 nightly

Oct 9 - Oct 10

Total with taxes and fees

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Top Olivebridge Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent

"Clean and nicely smelling place. Good breakfast. Friendly staff."

Urban Cowboy Lodge

8/10 Good

"The room was clean but a little smaller than we anticipated. Was hard to tell online. We did a tour of other available rooms would definitely choose differently next time. The property was amazing. We stayed during the week so it was so nice and quiet. We had the Japanese soaking tub which was great! We brought our dog and we were able to take her with us everywhere on the property. You’d never know that it was a pet friendly place as it is kept very clean. My ONLY negative comment would be that there is no where to get a meal that isn’t ridiculous expensive. I understand the limited menus in the area but everything was ridiculous expensive and very bougie food. Next time we would definitely pack some more snacks and food. Otherwise the place I awesome and worth the stay. We loved the robes! Wore them to our sauna appointment and then went and did a cold plunge in the river. So tranquil! We did not hook up the the WiFi so we stayed off grid for the three days we were there and that was just incredible. The staff were all super friendly and accommodating. What a fantastic place! Can’t wait to go back!"

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.

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Things to do in Woodstock

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.

Olivebridge Vacation Rentals

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Check prices for these dates

Our top choices for Olivebridge vacation rentals

1. Mid-Century Ranch * One-Level Living * Quiet Garden

2. West Wing - a unique private space w/patio

3. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

4. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

5. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

6. The Studio at the Inn at High Falls

7. Starlite Motel

8. Streamside Cottage Half Mile to Town of Woodstock

9. Woods Cabin-Kingston/Woodstock, NY.

10. Mossy Moody Cabin in High Falls, NY

11. LONGVIEW FARM - Reimagined Modern Farmhouse

12. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

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

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

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

16. Retro Retreat: renovated 2BR, desk, no chore list!

17. The Loft At The Inn At High Falls

18. Glamping Tent & Campsite by Minnewaska State Park

19. Cozy Mid-Century Retreat with Spa Hot Tub

20. Brand New House with Huge Patio

Find vacation rentals that suit your style

Top Olivebridge Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Find out more about Olivebridge

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