Vacation rentals in Sheffield

If you’re looking for a relaxing getaway, book this home! The Mountain View is breathtaking, even when sitting inside. The hot tub was all ready to go and the instructions were easy and helpful. Mary’s place had tons of board games and a wonderful entertainment system so you won’t run out of things to do. I would absolutely book this home again!

This place was a breath of fresh air. I've noticed a trend on AirBNB of rentals that are obviously flipped investment properties with no character and no evidence of life: this place is the opposite! Charming, comfortable, with hosts who actually know the area and live in the area. This is a great family option when visiting the surrounding Hudson Valley towns. I hope I can get back here soon!

Amazing house. Clean, super nice property, very well maintained, and lots of space. Great communication from host. And great location. Quiet property but a short drive to Great Barrington Main Street area with restaurants, coffee shops, and other cool little shops. Thanks for a really great stay!

Our host was very cool, friendly, flexible and hospitable, but what made him stand above all others as a host, was how available he was, texts were responded to in less than 2 minutes. The space and surroundings are beautiful as well, great find.

Lovely airbnb with lots of fun amenities (ping pong, darts, hot tub, fire pit, outdoor sunroom). perfect weekend getaway in nature! would def recommend

Tracie and Sean were very friendly. The house was very clean and well organized. Loved it!

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

Lockwood Lodge is a beautiful and peaceful place in a perfect location. Our families loved watching the snow come down from the big windows, the view is spectacular. Our kids loved the vintage video game consoles, the grownups loved the records and games/puzzles, and we all felt right at home in the lovely house. It was a perfect spot to hunker down in the snow storm. Jeremy was incredibly responsive and thoughtful and did much to make sure our stay was perfect. We hope to visit again in the summer to take advantage of the pool, which must be really special against the backdrop of that view.

A lovely stay in a peaceful area! Craig and Julie's home is full of thoughtful touches with their guests' comfort in mind, and you can really sense the love and joy that they have put into the house. Highlights include: an extremely comfortable and bright sunroom, a huge wraparound porch with many seating areas, the upstairs bedroom which is absolutely worth the climb up, and serene surroundings. We look forward to staying here again on future trips to the area!