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
$537 nightly
The price is $597
Nov 15 - Nov 16
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, (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
$186 nightly
The price is $208
Nov 15 - Nov 16
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, (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
$116 nightly
The price is $117
Nov 15 - Nov 16
Total with taxes and fees
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.

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, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
$195 nightly
The price is $196
Dec 1 - Dec 2
Total with taxes and fees
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

5. 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.
$118 nightly
The price is $119
Nov 15 - Nov 16
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
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, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveler
$268 nightly
The price is $300
Nov 15 - Nov 16
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Private kitchen

7. 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.
$182 nightly
The price is $203
Nov 15 - Nov 16
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

8. 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.
$452 nightly
The price is $500
Nov 15 - Nov 16
Total with taxes and fees
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A modern living room with a large window, a fireplace, and a cozy seating area.

9. 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.
$378 nightly
The price is $424
Nov 17 - Nov 18
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
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
$145 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
Starlite Motel
A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

11. 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
$286 nightly
The price is $320
Nov 15 - Nov 16
Total with taxes and fees
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
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.
$207 nightly
The price is $232
Nov 16 - Nov 17
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
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
8.6 out of 10, Excellent, (25 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
$290 nightly
The price is $325
Nov 15 - Nov 16
Total with taxes and fees
The Loft At The Inn At High Falls
A spacious living room with a fireplace, comfortable seating, and a dining area with a wooden table.

14. LONGVIEW FARM - Reimagined Modern Farmhouse

LONGVIEW FARM - Reimagined Modern Farmhouse
Marbletown
$1,583 nightly
The price is $1,614
Dec 8 - Dec 9
Total with taxes and fees
LONGVIEW FARM - Reimagined Modern Farmhouse
A modern kitchen with a large island, a sink, and wooden stools.

15. 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.
$520 nightly
The price is $583
Nov 15 - Nov 16
Total with taxes and fees
Woodstock Historic Artist Estate - The Carriage House
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

16. 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.
$207 nightly
The price is $232
Nov 16 - Nov 17
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

17. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$183 nightly
The price is $194
Nov 15 - Nov 16
Total with taxes and fees
Jessie's Harvest House
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

18. 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.
$641 nightly
The price is $718
Nov 22 - Nov 23
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
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.
$212 nightly
The price is $240
Nov 29 - Nov 30
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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.

20. 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.
$226 nightly
The price is $253
Dec 1 - Dec 2
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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 large, multi-story hotel with a symmetrical facade, multiple balconies with flower boxes, and a central entrance with a fountain.
Mirbeau Inn & Spa

Mirbeau Inn & Spa

Mirbeau Inn & Spa
Rhinebeck Village

10/10 Excellent

The staff was attentive and professional from Check-in through check out. The staff remembered who we were and accommodated all of our requests. Covid precautions were in place. The room is well appointed and very comfortable. The food at the restaurant (Willow) was outstanding. The spa area and “aqua terrace” (hot tub) were relaxing and delightful. We will definitely go back.
United States
Paula
Reviewed October 11, 2020
Mirbeau Inn & Spa

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 $117 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.

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.

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