Cottage holiday rentals in Middletown

We had a wonderful stay at Alexis' cottage! Our boys had a great time playing on the jungle gym & trampoline, playing basketball in the driving, exploring the woods, and we all took advantage of the hot tub and fire pits. The cottage was cozy and felt like home. We spent all of our time outdoors, and it was the perfect family getaway and we can't wait to come back!

Allison’s cottage is a wonderful spot! My partner and I spent a very nice week there. Allison was so helpful, responsive, and detailed. Every room was pristinely clean, and nicely decorated. The hot tub was the highlight of our stay. The cabin is located close enough to attractions, restaurants, and stores, but still felt quiet and peaceful!

The place was clean, beautifully kept and well supplied- we loved the backyard! Gabriela was very communicative. Highly recommend!

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!!

Our stay was absolutely wonderful! The house was adorable with everything you could want for a relaxing weekend away. We loved the hot tub and fire pit! The hosts included s'mores fixings and a bottle of wine..... Which was appreciated! Thank you for a wonderful stay!

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!!!

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.

The cottage was very clean and homey. Very convenient to new paltz and local hiking. Peaceful and quiet area. Plenty of fire wood and kitchen was stocked with snacks. We had a great stay and Amitai was very responsive and helpful. Would definitely recommend this place!

Adorable cottage absolutely ideal for unplugging and relaxing

This is our second visit to Camp Pocono Pines and it was even better than our first. We doubled our group size this go-round which made the experience even better. I loved the addition of the camp store, which wasn’t yet available the previous winter. I could imagine that as a great communal hangout during the summer months. Having a heating element in there would have made it useable during those chilly winter nights. We can’t wait for our next trip!

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.

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!

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!

Beautiful, comfortable home. Went up for a few days of peace and quiet and got exactly what we were looking for. The cottage is well stocked, clean, and cheerful. Clear instructions made check in/out and getting around the area a breeze. The stream out back burbled like something out of a fairytale and was the perfect background noise for a countryside getaway.

The host was very pleased understanding and easy to communicate with regarding the entire process. The house is the guest house for the establishment and is adorable. It is perfect for a small group weekend outing. The decorations and esthetics of the house are perfectly arranged to enhance the experience. The beds and linens are very comfortable, and both bedrooms are spacious and lovely. The host made checkout a breeze. We will definitely stay there again when we are in the area! :)

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!

This was our second time staying at the cottage. We had a wonderful stay over the holidays. The cottage was warm and cozy and Linda had tasteful and festive decor in every nook and cranny. We had the pleasure of meeting Linda. She is a truly wonderful person who loves what she does and it shines through in her beautiful property. So much attention to detail throughout the house. We hope to be back again soon!!

We had a wonderful and relaxing time at Stephanie's place! The cabin was very welcoming and comfortable. The kitchen was well stocked with everything needed to cook inside and outside. The beds and pillows were super comfortable. It was very easy to get a good night's rest there. Also, having the extra 1/2 bathroom was a great perk while traveling with teenagers! We will be staying at Stephanie's every time we visit the Poconos from now on!

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.

Picture the scene, crawling out of a toasty warm bed, a dusting of snow outside as you brew up a pair of espressos. The heady aroma entices my lovely bride of 27 years to poke her nose out from under the duvet. As we enjoyed our first sips we were treated to the excited chortling and gobbling of over twenty turkeys as they passed by the cabin. The peace and quiet was punctuated by the occasional woodpecker and wild turkey. We enjoyed a glass or two of wine sitting in front of the warm glow of the wood stove. Peace - quiet - nature - comfort - The Cabin gave us the pause we needed - we recommend everyone, young and old to slow down, reconnect, discover each other in this beautiful cabin in the woods!