
House holiday rentals in Olive
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Top-rated house rentals in Olive
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Popular amenities for house rentals in Olive
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

Hudson Valley Hygge House~ comfort in the country!
My boyfriend and I were looking for a relaxing weekend escape from NYC and couldn’t have picked a better spot. We came to explore Kingston but loved the house so much that we were just as happy staying in, playing games, and soaking in the cozy vibes. The home is beautiful and thoughtfully appointed — I can only imagine how magical it must be in the summer with the porch, or in the fall with the foliage. Even in late winter, it was idyllic. The location is perfect — just about 10 minutes from Kingston, so it’s super easy to pop into town while still feeling tucked away. We’d absolutely stay here again!

Idyllic Forest Home
What a wonderful, stylish home tucked away in the woods and with all the comforts of home. The indoor and outdoor spaces were both ideal for visiting, relaxing, and listening to music (what a sound system). It is perfectly situated close to Woodstock, Saugerties, Kingston, and numerous other attractions. Henry was a kind and responsive host, and always quick to respond to all of our questions. Highly recommended and a definite revisit next time we're heading upstate.

Gingerbread House- a 1950s Catskills Chalet
Elizabeth’s cottage is the perfect home base to explore everything in the Catskills, especially many of the hiking trails. The Urban Cowboy Lodge is essentially next door and offers a great restaurant for dinner and drinks without having to travel into one of the nearby towns. The cottage is also really a unique space with an eclectic mid-century vibe. Definitely will stay here again.

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!

Modern Mountain Retreat with Views on 18 Acres
Another review said it was more beautiful than the pictures and I agree! The home and space was so serene even though it was a bit rainy. My partner and I felt safe and visited some food recommendations. We highly recommend mornings! And We hope to go back! Paul was truly an amazing and responsive host
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!

Kerhonkson Forest House
Inssaf’s airbnb in Kerhonkson was beautiful, clean, and just as described. Their home office setup was perfect for working remotely. There are many good restaurant and cafe options in the surrounding town, so we didn’t spend a whole lot of time cooking, but the kitchen had everything we needed to make breakfast in the morning before heading out for our day-time activities. Highly recommend!

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!

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
₹1,731 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
Destinations to explore
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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
- Bash Bish Falls State Park
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Mount Peter Ski Area
- Opus 40
- Bull's Bridge Golf Club
- Thaddeus Hait Farm
- Plattekill Mountain