Cottage vacation rentals in Olive

The hosts were responsive and welcoming and flexible! Thank you for your hospitality. The home was clean, cozy and peaceful. it was a great getaway from the city life. Definitely recommended!

My family had a wonderful stay in Danny and Travis' house. The interior was clean, beautiful, and matched the photos in the listing. The yard was lovely and quiet. We felt away from it all, while still being close to great hiking trails and dining options. Danny and Travis had very clear instructions for how to get in touch with them if we needed anything, but it wasn't necessary. It's clear they put a lot of thought and care into making the process easy for their guests, and we didn't have any issues. The only thing I will caveat is that the house is located off a gravel road, which was quite bumpy when we visited (mid-April). This wasn't an issue for us, but would be a good thing for potential guests to keep in mind.

We had a nice, quiet stay at the cottage. Bilen was a responsive host when we needed to reach out during our stay. The cottage was clean with basic amenities, but if you plan to cook then make sure you bring/buy everything you need as basic pantry items (aside from cooking oil and salt/pepper) are not provided. We enjoyed using the hot tub, which was conveniently located on the back deck. Highly recommend stopping at the Monticello Bagel Bakery at least once during your stay for delicious NY bagels!!

I cannot say enough about this home. If you’re looking for a peaceful getaway with beautiful views, this is the place for you. Hosts were extremely helpful & very quick to respond. We got lucky with beautiful weather and got to enjoy the lake but, stargazing in the jacuzzi at night was a perfect touch. We seriously loved every bit of this home and would love to return one day!! Thank you Bob & Julie!!

We will go back for the summer!! They are absolutely the best! I felt like home!! They didn't make us feel uncomfortable!! We felt like that was our home!! Thank you so much for all!! You guys are absolutely the best!!!

We loved this house! The location is beautiful with a lovely view of the stream. The house was super clean and very nicely decorated. Dan gave us very specific directions for everything. The hot tub was a nice plus. The house is in a neighborhood, but it is nice and quiet. Having only one bathroom on the first floor was a slight inconvenience, but that would be the only negative I can think of.

Martin's house was tastefully decorated and free of clutter. The surroundings were beautiful and quiet. The house was a short drive from charming downtown Kent and several hiking trails. My kids especially appreciated the large television, games, and hot tub.

We had a wonderful stay at Diane’s. We were looking for a weekend away without the kids to recharge. We were able to do just that. We enjoyed the hot tub, and curling in front of the fire with a book. It was a snowy weekend but that just added to the charm. Diane’s scones are also amazing!! Diane made sure to communicate clearly and we were given all the info we needed to have a great time.

I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.

Adorable cottage absolutely ideal for unplugging and relaxing

House was great location, very comfortable- Kimberlie was awesome, thanks for your kindness. Lauren N

Darla’s cottage was such a sweet spot for a weekend getaway. Super cozy, clean, and peaceful—exactly what we were looking for. It felt tucked away in the woods but still really easy to get to, and just a few minutes down the road from Rough Cut Brewing, which was a big plus. We loved being able to grab some beers, then come back and relax inside. Darla was a great host—friendly, but gave us plenty of space. Would totally stay again next time we’re in the area!

My family, dog and I had an incredible weekend visit! It was our first time to the area and we already want to come back. Consuelo was a fantastic host! Consuelo was so easy to get a hold of for questions and was so friendly. The place was very organized, quaint and gorgeous. Thank you for a fantastic time! :)

Nice house in an excellent location equidistant from Milford and Narrowsburg. Olga was attentive and responsive. We thoroughly enjoyed our stay.

Loved our stay in this beautiful cottage, perfect for the 2 of us. Extremely clean and beautifully decorated with a TV that had all the movie channels. The kitchen was well equipped with everything needed, including delicious coffee . The bed was incredibly comfortable, slept like a baby. Pillows and blankets added to the comfy feel of home. Mark is a wonderful host who insured that the driveway was free of snow and ice prior to our arrival Highly recommend visiting.

Debra and Mike were great hosts and have created a very warm, inviting and comfortable place for those seeking to explore the Catskills. It's a home away from home! There's a grill available which we made great use of, a fire pit to enjoy nature and star gazing, and their two dogs Luna and Roxy are extremely friendly. Highly recommend their place!

We had a perfect long weekend at Steven's cottage. It is bigger than it looks in the photos and was immaculately clean when we arrived. Steven was extremely responsive to all our questions and needs. The place is incredibly peaceful, a 2 min walk from the lake, on a private road where Steven owns all three houses. It was so relaxing and rejuvenating to spend time at this oasis with my partner and our best friends. There's a lot to love, but the best part is that the house comes with a private deck and dock, and unlimited access to various boats, to make your lake weekend whatever you want it to be. We loved that we could take our dogs to play fetch off the dock and not worry about getting in anyone's way or having to share any space. It was a great stay and we hope to go back!

This cabin is so very special—and has an artists touch! It is cozy (especially with the wood stove going), spacious for being a one-room size, and has everything you need to disconnect and recharge. We will absolutely be back and appreciated the clear and easy communication as well!

Amazing place to stay - Book here!

We had a lovely stay at Monica’s place. It was a cozy getaway from the city and we had a wonderful weekend trip to the nearby towns. The space is exactly as listed and even cuter in person. Highly recommend!

My husband and I stayed here with our toddler and had an amazing mini getaway from home for a few days! The place was easy to childproof with the baby gates and outlet covers we brought from home and our baby loved exploring the new space. My husband is an avid fisherman and loved the area and caught some trout right near the house! We would recommend this place to anyone who wants to disconnect and be in nature for a while.

Such a beautiful place in a gorgeous setting. Clear communication from Victoria made it a sealed and highly enjoyable stay!!

What a wonderful place—cozy, warm, and incredibly inviting. Our hosts went above and beyond to make us feel welcome, even texting us weather updates when it started snowing to make sure we were safe. Their thoughtfulness really stood out. We truly enjoyed our stay and are already thinking of coming back in the summer to experience the beautiful countryside in a different season. A solid 10/10—highly, highly recommend!

We were expecting a peaceful, rustic, laid-back experience, and that's just what we got...and more. The cottage is situated in a lovely setting surrounded by trees, right at the edge of a picturesque brook. The inside was all we could ask for and more. So inviting and clean. Oozing warmth and charm. Every time we needed something, we could find it already supplied. The hosts clearly have thought of everything. We also loved the surrounding area. We spent lots of time in local eateries, checking out the nearby towns, and visiting the dozens of antique shops nearby. We had a wonderful time.