Twin Gables of Woodstock

Our stay at Twin Gables in Woodstock was nothing short of amazing. What was supposed to be a 2-hour drive turned into a 4.5-hour journey thanks to holiday traffic and a major storm that knocked out power across the area. Despite arriving well after hours, Leann—who normally closes the front desk at 6 PM—waited over an hour just to personally welcome us. That level of kindness and hospitality is incredibly rare. To top it off, I had mistakenly booked the room for two adults instead of two adults and a child, so our original room was quite small. Without hesitation, Leann upgraded us to the most beautiful room we could have imagined. It was beyond generous and made a world of difference after such a long day. The house itself is full of charm and character, perfectly preserved with thoughtful details throughout. The rooftop deck is stunning—ideal for catching both sunsets and sunrises—and the location is unbeatable, right in the center of town. If you’re planning a trip to Woodstock, do yourself a favor and stay at Twin Gables. Leann’s warmth and generosity made our visit unforgettable. Thank you, Leann, for going above and beyond—you truly made our stay something special

Woodstock has its own vibe, and Twin Gables matches it perfectly! We can’t imagine NOT staying here when we come back. It’s within an easy stroll of the Friday afternoon drum circle, great restaurants like The Pub and The Pearl Moon, and superb watering holes like Small Talk and The Colony. Leann and Jen were superb hosts, Room #3 was gorgeous, and the 8a breakfast was both simple and surprisingly nutritious.

I recently had the pleasure of staying at Twin Gables and it was a wonderful experience. This historic inn is full of character, and artistic flair the reflects the spirit of Woodstock What made the stay truly special was the hospitality of the innkeeper, LeAnn. From the moment I called for a same day reservation she was helpful and very accommodating. Once I arrived, I was greeted warmly and promptly checked in with detailed explanation of the amenities. In addition, she offered great recommendations for local interests. Her attention to detail, genuine kindness, and deep knowledge of the area really enhanced the entire experience. Since my first stay I have returned two more times. I have found the house to be very quiet and relaxing and a great change to staying in chain hotels .

Our hostess has taken this 100 year old Rooming house and updated everything in it. Each room is decorated beautifully and with a nod to the history of the Woodstock concert and the legacy of that era. The common room has a painted portrait of Jimmie Hendrix for example. The bed was very comfortable and the bathroom was newly remodeled and very large. The continental breakfast was fresh and fantastic and the coffee machine in the coffee nook pumps out delicious coffee 24/7. Near to the Museum and its galleries is the heart of downtown Woodstock. Easy walking to shops, it’s a fun way to explore this historic town.

The house itself is really lovely, the decor is fabulous, our room was luxurious and comfortable. Everything was so clean. There were lovely touches such as the snack basket with items for purchase. The towels in the bathroom were spotless and felt like new. The house is in the centre of town yet it is very quiet. We even saw a deer outside

A completely original boutique bed and breakfast hotel in the heart of Woodstock, NY. The rooms are all uniquely decorated, clean and comfortable.|The host, Leanne is very welcoming and helpful and provides a very lovely breakfast each morning.|Our stay at Twin Gables made for a perfect weekend in Woodstock. |I highly recommend Twin Gables.

1-location great. Close to town but many establishments have limited hours/days. |2-large first floor room (#1) was clean land had a great, large, white, clean bathroom (important!)|3-hot humid weather was a challenge for the room mounted air conditioner. While cool it was very damp. Unit did not remove humidity well enough. |4-nice to have 24 hour Keurig with choice of coffees and creamers!|5-breakfast was disappointing for a B&B. My wife and I were offered a single plate with one croissant, one slice of toast, and one slice of carrot loaf. There were some cold hard boiled eggs but that has limited appeal (I understand inability to cook there). A much more desirable method would be to provide trays of pastries on a counter and allow guests to choose what they want. I didn’t feel comfortable asking for another croissant. |6-the exterior front needs some serious upkeep. Not at all appealing and definitely does not look as presented on website. Could have a much better curb appeal |7-community room was comfortable and fitting for Woodstock.

A warm welcome to a sweet spot! Overlooking Tinker Street, steps away from everything. Tastefully updated and super clean, the bathroom was spa-like and the bed was easily the most comfortable we've slept in in a very, very long time. Twin Gables was definitely a bright spot on our stay, very highly recommend!

Leanne was super friendly and warm, providing us with an informative tour of where everything were. Leanne showed interest in our lives and was quite a pleasure to converse with, sharing the history of this place which she took over 3 years ago! Our room was decently sized and the air conditioning unit was efficient in keeping us cool during the summer heat. Our pillows varied in sizes and we sunk into the bed, which we didn't really enjoy but that's just our personal preference. If you're a light sleeper like I am, be prepared to wake up quite often when other guests goes in and out, for the walls are quite thin and certain rooms require more force in order to close/lock the door, so the sounds will definitely bleed through. There were also no body wash available in the three shared bathrooms. The shampoo and conditioner were also quite challenging to squeeze out from their tiny bottles. Breakfast was served from 8 to 10:30am, which encompassed a croissant or blue berry muffin, some mixed fruits, a glass of orange juice, and they have readily available coffee K cups and a variety of milk, ranging from whole, half and half, and oat milk. The breakfast was just a simple continental breakfast, where almost all the items were pre-made, which felt a bit underwhelming perhaps because we've been to Bed & Breakfasts where we received at least some simple home cooked breakfasts like eggs or French toasts. Overall, our best experience here was talking with Leanne; we really enjoyed our conversations with her! There are a lot of room for improvements, so I hope this review will help them continue to grow and become even more amazing. Thank you for reading and best of luck! (:

Very nice bed and breakfast in downtown Woodstock! The hotel manager was so kind and welcoming upon our arrival. I was a little skeptical about staying in a B&B since we usually stay in typical hotels. It's a lot more intimate staying in a B&B. They have three bathrooms that are used by all the guests at Twin Gables. I didn't feel comfortable showering there but we only stayed for a couple days. Just be aware of that before going. We were given a quick tour of the place. They have a nice sitting area with great 60s decor. They offer complimentary breakfast and coffee in the kitchen (extremely cute space) but we didn't partake in that. Instead, we visited a couple nearby spots for our meals. Our room, The Princess Room, was adorable. The bed was comfortable enough for two. I was a little bummed out at first by no television but we didn't really spend much time in the room at all. We spent most of our time exploring the area, as you should on vacation. Twin Gables is located towards the end of the downtown area. All the shops and everything you want to see in town is just a quick walk away! If we come back to Woodstock, which I'm sure we definitely will, we will certainly visit Twin Gables again! Thank you for a wonderful stay! ~Sophie K.

The pros of the Twin Gables of Woodstock are its location, location, location within walking distance of much of the town. The decor, as many reviewers note, is cute and Woodstock/60s themed. Some elements of the decor like paint, rugs and sofas look on the shabby side of shabby chic, and it's safe to say this has been the decor for quite a few years now. That said, the bedding and towels are all nice and new and certainly pristinely clean. We were quite disappointed in the breakfast. A bed and breakfast should make the breakfast worthwhile. The fresh cut up fruit was nice, but otherwise, tiny individual cereal boxes that are mostly sweetened kids' cereals, one choice of yogurt, and heated up "pastries" from the freezer were on offer - this in a town with many amazing bakeries is criminal. The manager offers juice but is quick to remind guests they need to get their own Keurig coffee, milk for cereal, and water from the little coffee nook. This would be a nicer stay if there was a better breakfast - either great fresh pastries, or at least some adult cereals, toast and brewed coffee. Or just offer beds without breakfast.

Want a dream of a B&B! The location is perfect, the vibes are very on brand for Woodstock and LeAnne, who manages Twin Gables was THE BEST. She made our stay! We can't wait to come back to Twin Gables!

This is the most adorable, unique B&B you will ever stay in, hands down. It is so perfectly curated that you won't be able to stop finding cool pieces to look at. Lee Anne is amazing and willing to accommodate you in every way. (Thank you so much for having nondairy yogurt! ) She is super nice and we loved chatting with her about Woodstock and life! The location is perfect, walking distance from everything you need and Lee Anne had some great recommendations. We cannot wait to come back

I had not been back to Woodstock in 30 years and I decided to drive up for a day. I made a reservation at Twin Gables because I remembered that it was right on a tinker street close to everything. I was delighted to find that it has gotten a chic boho makeover while still maintaining its charm and quaintness. The manager was exceptionally friendly and accommodating letting me check in very early and then switching me to a room she thought would be more to my liking. Later she made a fire outside and poured me some wine and I sat and met some very nice guests. I told her about a disappointing dinner I had and she brought me out some snacks by the fire. The room was very cool and comfortable and the manager is amazing. I wish I could give the place more stars and I will definitely be staying here any time I am in Woodstock.

A wonderful, wonderful place to stay. We were there for the Halloween weekend with our kids and loved every minute of our visit.

Not usually one to review after a single visit but hotel visits often are first and last visits. So first impressions are important! Happy to report the service was delightful and attentive. The space is a cute little renovation of an old building. Each room has a unique personality and the common areas are all clean and inviting. During a weekday visit we were one of the few rooms so almost felt we had the place to ourselves! Cute little basic breakfast with wonderful service. We were truly lucky to benefit from good timing. The outdoor gazebo is more enjoyable in the winter with a fire! Apparently you can request a fire and the other room had done so to our good fortune. We will certainly stay here when the need arises again. I'll say we were blown away by the service as just expecting a little inn.

Great location, you can walk to everything. Breakfast is just wane fruit and warmed up muffins and cereal. Firepit in the backyard after dark. Funky decor. Not worth $400 a night. Room #1 was funky. Narrow tub, no closet rod or hangers. I guess you could fit three in there, a couple in the king size bed and a single in the day bed, but it would be tight. Old house expect to hear every step someone else is taking anywhere in the house.

My friends and I had a wonderful stay here for my birthday weekend! First, we were warmly welcomed by Leann who made this weekend extra special! She was friendly, helpful, accommodating and just an overall awesome person! Thank you for your hospitality! In addition, the location was superb! Here you're within walking distance of tons of restaurants and shops. Parking was no issue, found a spot in front each time...I'm sure Covid and the cold helped a bit. Lastly, I loved the decor! It has a lot of character and I love how each room is designed with a different theme. So there's something for everyone to enjoy. We stayed in room 1 which had a private bathroom which I appreciated. My only compliant is that I wish there was more food offered for breakfast. I enjoyed the fruit, yogurt and pastries but would like more substance in the morning especially since there's a full kitchen. Also, bring a yoga mat if you'd like to practice in their meditation room.

Love this hotel. Cool and beautiful. Every room is spectacular. Katharine the manger was the nicest and warmest person overall we had such a great time!!!!

For location & style, Twin Gables of Woodstock can't be beat. All of the rooms--guest rooms, common spaces, kitchen, outdoor spaces--are beautifully appointed & LeAnn is a font of information when it comes to local eateries & attractions. Not only did she provide a recommendation for a local florist so that I could order flowers for my boyfriend's birthday, but she had them installed in our room prior to our arrival. Given that it rained every day of our vacation, I'm glad we had someplace lovely to curl up & read a book.

Would highly recommend! The staff was absolutely unbelievable- so kind and thoughtful and even gave us a tour of the house and we got to see the decor and shared spaces as well. Rooms were stunning as well as the whole entire house. Wonderful breakfast and coffee/tea bar with water. Centrally located on the main drag of Woodstock. Such a lovely place, would highly recommend!!

I stayed here on New Year's Eve and New Year's Day, and it was a very cool, artsy B&B! I stayed in the black and white-themed room on the first floor, which was very clean and had a private bathroom. The living room has very groovy vibes and has a vintage record player with nice tunes, so you can play DJ by the fireplace. The manager was very friendly and accommodating. She gave us free prosecco to celebrate with and was helpful when it came to suggestions on where to explore in town. Would definitely recommend as the best place to stay if you're visiting Woodstock. :)

twin gables was the perfect place to spend two nights in Woodstock. the inn keeper LeeAnn was friendly and helpful and made our stay so fun.

Very nice little B&B. The accommodations were excellent, comfortable bed and nice shower, very quit while sleeping. The staff was very friendly. The breakfast was great, fresh muffins scones, yogurt, OJ and coffee/tea. The corn muffins were actually the best I have had in a long time I'm going to find out where i get them next time and bring some home. Everything in town is within walking distance which is great also. Also very honest! I left my kindle in the room by accident when I checked out, I got a call that night and the kindle was mailed to me the next day. This will be the only place I stay at when I visit Woodstock.

A very nice B and B! Great location, everything you need is walkable. They have very nice quaint rooms, and ours was room #1 on the second floor. We had a private bathroom and the bed was very comfortable. The shower was nice and breakfast was good, coffee and tea are always available. We had nothing but good things to say about this B and B! I would happily come back!

My mom, Aunt, and I went a couple months ago for my birthday and it was amazing. LeeAnn was so sweet and very welcoming. She made the whole experience so much fun and it definitely made my birthday weekend so special. The room was beautiful along with the whole house! Everything looked so great. For anyone looking to stay somewhere beautiful and welcoming stay here!

Wonderful first trip out of Maine in 16 months. The inn is beautiful and beautifully run by Leanne who went way above and beyond when we explained that friends we were meeting didn't feel comfortable with indoor dining. She let us host our friends in their gazebo out back which saved the day at the last minute. We would definitely return if back in charming Woodstock.

We are so glad we found this beautiful boutique hotel! It was a quick 2 Hour Drive for us and we are so so happy! Everything was perfect! Great breakfast brought to your room, a beautiful meditation room, cute backyard and all the rooms are stunning. I would definitely recommend and we are coming back soon!

The room I stayed in had sunshine that streamed through the lace curtains. I sat in the reading chair each night I stayed here. This place might not be for everyone. The walls are thin and the house is old - it was exactly what I was looking for. Shopping and eateries are within walking distance and if you want an extra treat splurge at the River Rock spa - two minutes away. The place is spotless, feels like your grandma's house and has beautiful bath products. The owners leave you alone.

Absolutely wonderful place! The room had a very cozy feeling. The house had a very unique feeling to it, and was very well decorated. Very helpful staff too. Loved my stay here and will definitely stay again when I go back to Woodstock. Additionally, felt very safe COVID-wise. Masks were mandatory and the space looked clean.

We loved this hotel! The room was so cute and very clean. The staff was super friendly and welcoming! They even brought a warm muffin and croissant for breakfast. Walkable to all the shops and restaurants, highly recommended.

I was worried about this place after reading one of the reviews but my experience was very good. This B&B is really only one block from the center of Woodstock and very close to everything. It was also the least expensive I could find! It was quiet clean cool and comfortable.

The Twin Gables was an incredible place to stay. I was in room 5 for three nights and I have absolutely no complaints. For a bed and breakfast, I was especially happy with how well maintained the bathrooms were (as you have to share the upstairs ones with others). The shower was always cleaned and towels always refilled. They offer a straightforward breakfast in the morning and the location is right in the heart of town and not too far from equally charming towns such as New Paltz and Kingston. Come check it out, it's beautiful here!

Twin Gables is great! There is a sort of 19th-century feel to the place, and it's very relaxing. It's in the middle of Woodstock, too, so it's walking distance to a bunch of restaurants and things to do. The breakfast was pretty typical stuff, and if you're in Woodstock, you probably want to go a few blocks down the street to Oriole 9 for breakfast anyway. All in all, a very nice place, and the rates are reasonable. We have stayed in room 1 several times, and recommend it.

Cute! Like going back in time. Warm and inviting. Love being right in town. Middle of Woodstock. Everything is easy and convenient. Bus stop just a couple blocks away.

Very pleasant experience with warm and welcoming service. Breakfast was good fresh fruit, yogurt, muffins, oj and coffee. Great location and I would visit again.

We had a great visit this weekend. The place was super clean, the location was ideal, the manager (Nancy) was warm and welcoming, the bath products were really nice, and the breakfast was simple and fresh. Couple of caveats: 1) the bathrooms are shared, and 2) floors and doors in the house were pretty loud. Overall, it was a great experience and we'll be coming back.

My sister and I have been using the Twin Gables Bed & Breakfast for the last five years consistently as our lodging when we stay in Woodstock. Recently the establishment disappointed us with their rude and unprofessional behavior. We made our usual reservation for January 20 2014 and both traveled 3 hours each to be greeted by a rude receptionist. He was appalled that my sister had her 3 year old with her when she walked through the entrance. So much so that my sister couldn't even give me a hug as he shouted and yelled at her, "Children don't stay here!" She apologized that she was unaware of such a policy and we had previously stayed there when he was about a year old. She calmly asked to speak to the owner and said if it was a problem to just refund her credit card. The receptionist who was on the telephone with the owner said, "He's on Wall Street and he is too busy to speak to you. Get your bags and leave immediately." My sister and I complied, but were shocked at the barbaric treatment we received as he practically threw our bags on the street while she was asking to get the refund. My sister called Twin Gables to follow up on her refund shortly after our trip. She spoke to women on the phone that told her that she was a liar and had never stayed there with the baby prior to the incident and when asked about her refund said "She should know better." We understood the policy and were just asking for our refund. I find the way the situation was handled a disgrace. I would have liked Twin Gables to issue the refund without the unprofessional dramatics. I will attach a photo of my sister, mother, and baby in Twin Gables prior and can assure you my sister did not sneak him in and is no liar.

I recently stayed for a last-minute Friday and Saturday night. This was my first time in Woodstock. I was warmly greeted at the door by Nicole, who showed me the comfortable living room and coffee alcove of this charming Victorian guesthouse. Although they have wifi, there are no TVs or radios in the rooms. Great place for a digital vacation! She kindly offered assistance with my questions about local transportation. My room was a small single room, next to a shared bath. The bed was comfortable and the Hitachi mini-split AC was very quiet and worked beautifully(it was a HOT couple of days). That night I went to see the Milk Carton Kids at Bearsville Theater, and upon returning, chatted with several guests in the living room. The next morning, breakfast was nice, with fresh fruit, pastries, and my favorite yogurt! (Brown Cow Maple). Guests tend to linger in the common area in the mornings and evenings, having coffee and chatting. Saturday night was similar, & after the Richard Thompson concert at Levon Helms' Barn, 6 of the guests who had attended, again chatted in the living room. Lovely guests. Sadly, I had to leave Sunday morning; however next time I plan to stay longer, and I will be staying at Twin Gables.