Vacation rentals with a hot tub in Olive

Ashley’s place was perfect! We were looking for a peaceful mountain getaway and it exceeded our expectations. The house is clean and beautiful, and it has everything you would need. Ashley was very responsive and left a great list of recommendations. I would definitely stay here again!!

Everything about our stay was amazing. The home was beautiful and had everything we needed. We loved the hot tub and the fireplace. The bed was very comfy and the heated floors were a nice touch. The WiFi was strong and reliable. Our senior dog felt comfortable and could easily navigate the stairs and property. We would absolutely book again when in the area.

House was spotlessly and thoughtfully decorated. The bed was comfortable and hot tub was absolutely phenomenal. Skylights let in beautiful natural light for reading and relaxing. Michael and Enrique were proactive about reaching out beforehand with the house information and we really, really enjoyed our stay. We're not used to baseboard heating so some of the noise from the heating surprised us, but that's to be expected with any place that's not your home. Would gladly stay here again.

This stay was amazing and we had a wonderful trip! The house was beautiful and very homey. Our host was very responsive and gave great directions for check in.

The house was exactly what we needed for our getaway. The rooms and furniture were clean and comfortable. We also enjoyed dining out and the variety of options nearby. The hot tub warmed our souls along with the natural landscapes. We appreciated the salted walkway upon arrival and the plowed driveway upon departure. It was a very relaxing weekend. Thank you.

Beautiful home! Very convenient to Windham mountain/town. We would definitely stay again

Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

We had a fantastic stay at Shane's place. The house was clean, comfortable and absolutely gorgeous. We were able to enjoy the hot tub and fireplace and had all the amenities to have a relaxing weekend with a few friends. Shane was very easy to communicate with and promptly responded to any questions we had.

My friends and I had an amazing time here!! The kitchen was incredible and we were able to make a multi course meal. The yard was beautiful, we felt safe and were able to unwind and hang out. The hosts were amazing and responsive, answering all of our questions and accommodating all of our needs. The house was clean and comfortable and I would happily stay here again :)

The house was lovely and very clean and Piotr was an excellent host and even met us at check in to show us around. There are 4 bedrooms and each bedroom has its own bathroom which was very convenient for us. The kitchen was well stocked and It was very comfortable stay for my family of 7 adults and two babies and two dogs. One bedroom is on the main floor and two bedrooms are on the walkout lower level and one bedroom is on the upper floor. To get to the upper floor there is a steep winding staircase that wasn’t an issue for us, but I would not recommended it for small children or toddlers. The outdoor hot tub was a nice addition.

My daughters and I really enjoyed our stay at Jacks place. The house is beautiful, and the surrounding private property is stunning. Nicole was very helpful whenever I had any questions.

I would stay at Alluvions place time and time again! It was nestled in such a private area but still felt close to everything we needed. The home was BEAUTIFUL, perfect for large families for the holidays. It was depicted exactly as shown, very spacious and stocked with everything a family could need (including a playroom)! Even though we spent 5 days there as a family, it didn't feel like enough as no one wanted to leave. Once you unpack, you just feel at home.

It was very clean, well-stocked in terms of bathroom and kitchen amenities, and had plenty of space for a large group to both spread out and find common areas. Hot tub, games, and large tables with plenty of seating. The host was responsive with any issues or questions we had. Very nice place!

We celebrated thanksgiving with our entire family. So cozy and well equipped. Beds were comfortable. The house was spectacular! Amazing views! So much privacy. The owner, Jean was very accommodating and went out of her way to make sure we had everything. The caretaker Kat was just the same

Yvette's home was absolutely wonderful! The place was spotless, beautifully decorated, and had all the amenities needed for a comfortable stay. The beds were cozy, the kitchen was well-equipped, and every little detail was thoughtfully arranged. Yvette was an exceptional host—super friendly, responsive, and always communicative. She made sure we had everything we needed and provided great local recommendations. I would definitely stay here again and highly recommend it to anyone looking for a relaxing and enjoyable stay.

We had the most amazing getaway weekend at Gal’s stunning home. Unlike other hosts, Gal was extremely proactive in reaching out and super responsive with any questions we had. The living space was very spacious with the huge living room couch plus the additional basement and game room areas that felt like a completely different side of the house. The bedrooms also had more than enough space to accommodate our group of 8 people. Our favorite part of the house was the backyard and hot tub area. It was extremely relaxing and peaceful. The fire place also kept us nice and warm and kept the living room nice and cozy. I would 100% rent this home again for the next time we look for a quick getaway weekend. This was a great value for what we got and we will definitely be returning in the future.

We thoroughly enjoyed our stay. The house is very clean, cozy and welcoming. The grounds are spectacular and the creekside sauna was delightful. We didn't see a single car on the road which was a pleasant surprise. A wonderful spot to relax and catch up with dear friends.

Olivia’s cabin was so cute! We really enjoyed our time there. It was so quiet and peaceful and perfect for a reset away from the city!

We had a fantastic stay at this charming cabin in Dehli, New York! The hosts were incredibly communicative and provided a spot-on description of the place. The cabin was beautiful, cozy, and a perfect retreat. Highly recommend!

The Little Log Cabin was the perfect long weekend getaway. It was so comfortable and cozy. I would love to return the next time I’m in the Catskills. Thank you Becca and Jesse for sharing such a wonderful home!

Perfect cabin getaway tucked away on a secluded road. Very convenient for skiing at Windham ~10 min drive. We enjoyed the hot tub, the cozy living room, and the comfortable memory-foam mattresses. Thomas was quick to respond to any questions we had. Would definitely stay again!

Ben’s cabin was beautiful! Such a lovely escape to a quiet spot in the woods. The hot tub is the best part :) the bathroom and kitchen are immaculate!

Wonderful stay at the cabin! It was negative 0 degrees and winds over 65mph during our stay but we would have never known ☺️ stayed warm and cozy with a fire going the entire stay! Finally got to use the hot tub on our last day which was PERFECTION! Snowy grounds surrounded by trees in a hot soak was exactly the experience I was hoping for. Excellent stay! Do note the driveway slopes up and was a sheet of ice - we have a car but rented something with 4WD to handle all the ice and snow in the area and still left it parked at the bottom as per Alan’s recommendation! OH! And the beds are INCREDIBLY COMFORTABLE! I’m an early bird but actually let myself sleep in :)

We had a great time spending a few days in the mountains. Gorgeous surroundings and almost entirely private. We weren’t able to use the hot tub due to the rain but we’ll be back during better weather. The wood fired stove was amazing and really lent to the coziness of the cabin. Highly recommended for those more towards the “glamping” style of vacationing.