
House vacation rentals in Olive
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Top-rated house rentals in Olive
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Popular amenities for Olive house rentals
House rentals with a pool

Shula | Farmhouse | Pool, Fire pit, Hot tub
Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!

Private Hudson Valley Country Retreat
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
Our stay at Susanna’s was perfect! We have zero complaints. Had everything we needed and more! We would definitely stay there again when in the area!

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Little owl Japanese teahouse: pool is OPEN
The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!

Harrison Field Pool Bike2Town FirePit 10AcreViews
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

Modern House with Private Pool, Hot-Tub, Fireplace
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!
Weekly house rentals

New Paltz Guest Cabin Nestled In The Woods
Beautiful location, peaceful and private. Spacious, modern, comfortable home. Really good advice about places to explore and visit in the surrounding area. This is a place we’d return to in a heartbeat. Just the tonic after a week in Paris and a hectic entry via JFK. Ben’s place is a haven away from the world. We just loved it!

The Woods House, 40 secluded acres & speedy wifi!
Donna's place was amazing! We knew we would love it from the pictures but were even more blown away when we walked inside. It was the perfect cabin with every amenity and more that you could want for a remote get away in the Catskills. We went up with our dog and loved every minute - will definitely go back for our next trip up!

Gingerbread House- a 1950s Catskills Chalet
Overall a great stay! The home was beautiful and exactly what we needed. Elizabeth was also a great host. We’d be more than glad to visit again in the future!

Olive Star Cottage & Garden
The cottage was modern and clean and provided all the necessities of home. The beds were very comfortable, the kitchen had all the basic staples, and the dining table had a perfect view of the backyard and surrounding wildlife (deer every morning). The location of the cottage is close enough to Woodstock village and Ashoken reservoir for daily activities.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
A very lovely place to stay! The description matched the place exactly. We enjoyed spending a lot of time outside on the deck bird watching and even saw some fish jumping in the river. The property is also very private which was a huge plus -- no visible neighbors in any direction while spending time outside. Seth was a very responsive host and did a great job with the design of the house. There were lots of thoughtful touches that made the stay extra nice. Would love to stay again!

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit
Excellent location with private pond. This home was truly built for a family gathering. Wonderful entertaining spaces, large fireplace with an expansive kitchen to cook in. There is a large game room with board games to suite all ages, billiards, croquet, and a small row boat for fun.

Modern Cabin on 7 Acres in Catskill forest w/ Pond
Great place to stay in the Catskills if you want something peaceful in the woods. It was a great price for how clean, quiet and aesthetically pleasing this place was. While it was off the beaten path, it was a short drive to many of the cool places in the area and the hosts give a great book of recommendations that was very helpful. Would stay here again!

Eagle Rock House
We were 2 couples staying for 3 days in June with a bit of a heatwave but AC was great. Rooms are big and not cluttered. Great master bedroom and master bathroom. Kitchen had everything we needed, got nice bread from Rhinebeck in the morning.
Private house rentals

Olive Woods House - Catskills Mountain Views
One of my best Air BnB stays ever: beautiful house, great amenities and a wonderful location. Already planning our next trip back!

Perch Eagle House: Creek access + Sauna + Mt views
Had a great time again in Olive. Nice little house close to the river. Would definitely come back again!

Country Getaway with Mountain View
This was the perfect vacation house in the woods for our family. My two young children loved all of the toys available. I quickly realized I did not have to even open the bag of books and toys we brought with us because there was more than enough here! Being in the middle of the woods was exactly what we were looking for. The house was well stocked with towels and all necessary cooking supplies. I would suggest a couple of extra blankets for cooler weather, as the bedroom downstairs was quite cold when we arrived. Otherwise, we had an excellent stay and we would definitely come back.

The Earthmover Inn
Staying at the Earthmover Inn was the best decision we made this holiday! The house was impeccably clean and cozy, and Roger and Ruth left lots of great treats, like small chocolates and coffee and tea. We had a blast playing Scrabble by the fire, and the whole stay was wonderful. Roger and Ruth are attentive and kind communicators, and you can tell they care a lot about the comfort of the folks staying here. The BNB is within 10 minutes of Stone Ridge, and only a few minutes away from Tetta's and the Country Inn, for closer options for groceries and food. I grew up in the neighborhood, and staying here while visiting family for the holidays made me feel right at home!

Midcentury House in the Catskills
Had a wonderful trip at this cabin. The space is cozy, thoughtfully decorated, and surrounded by nature — exactly what we were hoping for. The well-stocked kitchen made cooking a joy, and we especially loved using the outdoor pizza oven. The fireplaces and wood stove added to the warm, inviting vibe throughout the home. The property itself is stunning —the a creek and a pond were fun to explore. We even got to see tadpoles hatching in the pond! It felt like a true escape. Zachary was a fantastic host — super communicative and helpful from start to finish, which made everything easy and stress-free. Would highly recommend staying here!

Stone Ridge Farmhouse, w/ hot tub
We had a wonderful stay at the farmhouse in Stone Ridge. The house is comfortable and the kitchen is nicely appointed making cooking enjoyable. The property is quiet and private but close to Stone Ridge. Holly was quick to welcome us and provide all the info needed to settle in. We highly recommend the farmhouse in Stone Ridge if you are looking for privacy and relaxation.

Hudson Valley home with covered porch, fireplace
Great house/cabin for a nature getaway. Exactly as described, and I appreciated very clear instructions about everything. Loved attention to details and high-quality touches throughout the house and cute retro vibes. Very comfy beds and linens. We stayed over the Thanksgiving weekend, and were able to cook a holiday dinner for ourselves as the kitchen is fully equipped. The heating worked well considering freezing temperatures, but it makes some blowing noise, in case you are sensitive. I imagine that in warm weather this house sould be an absolute gem.

Catskills Haven With Private Creek
The house was clean and comfortable. We didn’t have any issues
Quick stats about house rentals in Olive
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Opus 40
- Mount Peter Ski Area
- Bull's Bridge Golf Club
- Thaddeus Hait Farm
- Plattekill Mountain