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
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Olivebridge vacation rentals

Exterior

'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, (47 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.
$145 nightly
The price is $162
Apr 26 - Apr 27
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing

"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Phoenicia
$275 nightly
The price is $284
Apr 27 - Apr 28
Total with taxes and fees
"Rocky Bottom" Cabin • Creekside • Fire Pit • BBQ • Fishing
Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (31 reviews)
"Lovely place almost magical ....the perfect get away . . So well kept."
United States
Nivia
$342 nightly
The price is $369
Apr 25 - Apr 26
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
$136 nightly
The price is $152
Apr 26 - Apr 27
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park
2 bedrooms, desk, free WiFi, bed sheets

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Mt. Tremper
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful spot to unwind and take a relaxing getaway."
United States
cheryll s.
$350 nightly
The price is $392
Apr 27 - Apr 28
Total with taxes and fees
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (34 reviews)
"Awesome place, great location. We loved our stay."
United States
Will R.
$144 nightly
The price is $147
Apr 28 - Apr 29
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (12 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$233 nightly
The price is $236
May 3 - May 4
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
$143 nightly
The price is $145
Apr 27 - Apr 28
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$450 nightly
The price is $504
Apr 25 - Apr 26
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
Smart TV, fireplace

Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (19 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.
$379 nightly
The price is $425
May 5 - May 6
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (25 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
$149 nightly
The price is $152
Apr 26 - Apr 27
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Outdoor dining

Catskill Cabin Little Owl Apt 1

Catskill Cabin Little Owl Apt 1
Shandaken
9.6 out of 10, Exceptional, (8 reviews)
"I enjoyed my stay at the little owl apartment. It was decorated very cutely, and felt very homey. The bed was very comfortable as were the linens"
United States
Benjamin
Catskill Cabin Little Owl Apt 1
Terrace/patio

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, (28 reviews)
"The beds were especially comfortable! "
United States
josh p.
$217 nightly
The price is $242
May 5 - May 6
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Fridge, microwave, oven, stovetop

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, (5 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.
$211 nightly
The price is $236
Apr 29 - Apr 30
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Fireplace, books

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, (14 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
$166 nightly
The price is $169
Apr 28 - Apr 29
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.6 out of 10, Exceptional, (9 reviews)
"Everything was perfect. Don’t miss the owners restaurant either it’s great "
United States
Matthew
$264 nightly
The price is $296
Apr 27 - Apr 28
Total with taxes and fees
Tiny Home, King Bed & Hot Tub, Unit B
Property grounds

Cold Spring Lodge - Cabin 2

Cold Spring Lodge - Cabin 2
Big Indian
9.6 out of 10, Exceptional, (4 reviews)
"We had a nice relaxing stay"
United States
Michael
$234 nightly
The price is $262
Apr 26 - Apr 27
Total with taxes and fees
Cold Spring Lodge - Cabin 2
Smart TV, fireplace

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, (10 reviews)
"Great place and very clean. Beds are very comfortable. Would definitely stay here again."
United States
Charles S.
$539 nightly
The price is $604
Apr 26 - Apr 27
Total with taxes and fees
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Property grounds

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
$295 nightly
The price is $334
May 6 - May 7
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Exterior

Tiny Cat Tiny House

Tiny Cat Tiny House
Grahamsville
9.8 out of 10, Exceptional, (7 reviews)
"Great location to get some peace and quiet. Beautiful foliage and tons of wildlife in the area. This was our first time staying in a tiny home, and the place had everything we needed to cook, clean, and relax while exploring the area."
United States
Jacob L.
$209 nightly
The price is $235
Apr 26 - Apr 27
Total with taxes and fees
Tiny Cat 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.
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"The staff was so cultural so friendly polite and smiling at all times also I left my credit card at the counter night before when checking in and they probably returned to me. I go back and get it again! "
JANE 1-night trip
Posted 8 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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 $129 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?

Deck, Hot Tub & Stunning Catskills Views | Suncliff Vista by AvantStay: Visitors like this Olivebridge vacation home rental. It offers a patio, a hot tub, and air-conditioning to help you feel perfectly comfortable 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?

Catskill Mountains and Esopus Creek are a couple of lovely local spots to get outside and enjoy nature. While here, Catskill State Park and Brown's Station are other places worth a visit.

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.