Olivebridge Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

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 19 - Apr 20
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (276 reviews)
"The view in the snow was absolutely gorgeous and the size of the accommodations was perfect!"
United States
Abigail Y.
$272 nightly
The price is $305
Apr 16 - Apr 17
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
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.
$384 nightly
The price is $430
May 5 - May 6
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
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
$262 nightly
The price is $293
Apr 21 - Apr 22
Total with taxes and fees
Tiny Home, King Bed & Hot Tub, Unit B
Exterior

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.
$303 nightly
The price is $339
Apr 16 - Apr 17
Total with taxes and fees
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
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.
$218 nightly
The price is $220
Apr 19 - Apr 20
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Smart TV, video games, offices

Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access
Saugerties
9.6 out of 10, Exceptional, (15 reviews)
"The home was extremely clean and nicely appointed. Beds were very comfortable and kitchen was nicely equipped."
United States
Nancy B.
$252 nightly
The price is $273
May 6 - May 7
Total with taxes and fees
Peaceful Cabin w/ Fire Pit & Creek Access
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 19 - Apr 20
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, (30 reviews)
"Best place ever!!"
United States
LaurapatOsterwald S.
$345 nightly
The price is $372
Apr 16 - Apr 17
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
2 bedrooms, desk, free WiFi, bed sheets

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

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
$250 nightly
The price is $280
Apr 29 - Apr 30
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
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 16 - Apr 17
Total with taxes and fees
Tiny Cat Tiny House
Pool

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
Hunter Highlands
10.0 out of 10, Exceptional, (12 reviews)
"We couldn't ask for a better location for snowboarding at Hunter. Nice apartment. We'd definitely go back next time."
United States
Rui
$189 nightly
The price is $206
Apr 16 - Apr 17
Total with taxes and fees
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
Interior

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (74 reviews)
"Wonderful tiny home. "
United States
Kyle E.
$219 nightly
The price is $245
Apr 16 - Apr 17
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
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.
$212 nightly
The price is $237
Apr 21 - Apr 22
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.
$174 nightly
The price is $176
May 6 - May 7
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior

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, (22 reviews)
"Great stay!"
United States
Olivia O.
$119 nightly
The price is $121
Apr 16 - Apr 17
Total with taxes and fees
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Bar (on property)

Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (1 review)
"cute little spot! very nice place to stay"
United States
David R.
$188 nightly
The price is $199
Apr 16 - Apr 17
Total with taxes and fees
Jessie's Harvest House
1 bedroom, free WiFi, bed sheets

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, (34 reviews)
"Instructions were clear. Accommodations were comfortable and clean. Lovely grounds. "
United States
Julia
$256 nightly
The price is $287
May 10 - May 11
Total with taxes and fees
The Studio at the Inn at High Falls
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.
$190 nightly
The price is $193
Apr 27 - Apr 28
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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.
$226 nightly
The price is $253
Apr 19 - Apr 20
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"We stayed at a room with loft. "
Heeyoung 1-night trip
Posted 1 day ago
Hunter Lodge, a Bluebird by Lark

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?

Esopus Creek modern Tiny house Retreat!: Visitors like this Olivebridge vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Olivebridge?

Choose from 10 Expedia vacation rentals in Olivebridge for a memorable vacation.

What can I see and do in Olivebridge?

Esopus Creek and Catskill Mountains 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.