Cottage vacation rentals in Woodstock

Pictures don’t do justice! Craig’s place was lovely, from the amazing kitchen to the spacious living room and the outdoor patio. For a group getaway this is the perfect place. Would stay here again in a heartbeat!

The perfect place for a cozy getaway from the city! We really needed an R&R and this place gave us what we needed and would be happy to come back here again ✨

Nice little getaway during the cold season. The hot tub was excellent and about 100 degrees so perfect even with the cold temperature. It was still possible to put together a meal with the propane grill and warm things up in the microwave or store them away in the fridge. The heat was excellent in the space. Seems like it would be a great place to stay in the summer as well!

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! :)

The White Bunny Cottage is a lovely house that was super clean, cozy, and had everything needed for a great stay. Check in and check out were extremely easy. Lisa was always very quick to respond to all of our communications. She was always kind and professional when communicating with us. The house has a nice location within the Sleepy Hollow Lake community. It sits off the road a bit and surrounded by trees which makes it nice and private. Beds and furniture are very comfortable and the kitchen is well stocked. Airbnb photos accurately represent this beautifully decorated home. There is plenty to do in the area or you can just stay at the home and enjoy the deck, firepit and indoor gas fireplace! We already booked another stay in June. Thank you Lisa and Gabrielle for sharing your home and ensuring that we felt safe and comfortable.

Marcos' house was perfect for a cozy winter stay with our young kids! The house has a very comfortable lay out for cooking, lounging by the fire and enjoying a beautiful winter scene from windows on all 4 sides of the house. It is both beautifully and comfortably decorated and feels very peaceful! We would definitely visit again!

Sunset Cottage was the absolute perfect place for us to spend a long weekend. The house is beautifully designed with modern touches like big windows with stunning mountain views. We loved the open lay out with the cozy living room and comfy beds in each bedroom that made it easy to relax after an upstate day. The cottage location is ideal with it actually being located in Woodstock vs many other airbnb’s that day they are but aren’t. We were just a 3 mins drive to Woodstock town where we had such good meals at Red Onion and Silvia, but felt far enough away to be immersed in nature. Each morning, we were greeted by a family of deer grazing in the yard! The house itself was incredibly clean and well-decorated, adding to the overall comfort and charm. The hosts were super friendly and gave us great tips on local hikes and restaurants. We're already dreaming of our next visit for a ski weekend or summer to use the pool!

We had an excellent experience with Todd and his cottage. It was a perfect weekend getaway. The space was very quiet and peaceful but close to local attractions. Todd had great recommendations for restaurants, shops, wineries, breweries, and other activities, all of which were no more than 10 minutes from the cottage via car. The space was small but appeared exactly as described in the listing. It was a perfect option for us and our dog. We would definitely return in the future!

My stay at the cottage was such a nice way to ring in my 31st birthday. I booked the house 5 days before our stay due to our initial airbnb reservation falling through the cracks and I am so glad it did in hindsight. This place had everything you could ask for, a hot tub, indoor fireplace, in close proximity to Woodstock, comfy beds + hangout areas. Overall our stay was so peaceful and everything we were looking for. I wouldn't hesitate to book your stay!

This home was everything we hoped it would be. It offered a peaceful location for our family (two kids, 4 and 2). The home was cozy and the recommendations from Nadia were great. We went to several of the recommended restaurants as well as the Teddy Bear museum and hiked the Rosendale Trestle. Truly a wonderful stay.

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 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 always stay at Little Willow when we go skiing at Belle Ayre. I think our three years and running relationship with the house tell you all you need to know about working with the Little and Littler gang and their spot.

We had the perfect stay for our Thanksgiving. Lots of toys for the kiddo, backyard for the dogs to run around, and a well-stocked kitchen for all our cooking needs (utensils, platters, etc). Sadly we didn’t get to use the play set or the fire pit due to the weather, but we hope to come back when weather is slightly warmer!

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.

We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)

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

A perfect spot to get away for the weekend. First, the view out the front door is top notch. Situated at just the right distance from town, we were able to hike, explore and eat well, and then easily head back to the Airbnb for some R&R. The area was peaceful, the beds were amazing, and the bathroom was fully stocked if we forgot anything. We checked out Saugerties Lighthouse to stretch our legs after travel. We loved breakfast at Josie’s, dinner at Miss Lucy’s and The Dutch, and ice cream at Sawyer’s. We explored some spots on the Hudson River School Art Trail: The Thomas Cole National Historic Site, Kaaterskill Falls, Platt Cove Preserve, and Falling Water Preserve. A perfect Catskills Airbnb that is dog friendly to boot! 10/10.

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!

"This feels like home already." That was my 8-year-old's response to this sweet Kerhonkson cottage, just one hour after we arrived. I could end my five-star review there but I'll add some perks listed and not listed, which we really enjoyed. Prime location. The cottage is within a 20-minute radius of so many wonderful spots. We come for the Bonticue Crag rock scramble but stay for Saunderskill Farm, Upstate Taco, Bluebird Wine and Spirits and so much more. The creek. My kids walked there barefoot and sunned on the rocks. If you're lucky: farm fresh eggs are sold on the honor system on the main road just past the creek. The shower. You'll see. Smaller perks: The back deck gets great sun. So much closet/drawer space to organize your stuff. Lighting options galore, and almost all of them on dimmers. Sonos sound system and a charging station. The cozy office space, in case you have to "check in" or if you just want some alone time. Thank you, Consuelo! We'll be back.

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.

Cute little pad to explore the Hudson Valley from! Would recommend to anyone looking for an easy-going place to stay in Pine Plains.