House holiday rentals in Sturbridge

This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

Brad was very friendly and helpful. Beautiful home!

From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛

This place was great, an easy drive to all the hotspots and a quiet neighborhood vibe.

We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Immaculate and comfortable. Well stocked. Beautiful location. Owner was excellent. Very responsive and friendly. Would without question stay here again. Great base of operations for Brimfield Antique Show.

If you’re looking for a serene and restful place to come “home” to after a day out and about…this is the place to stay! The central location allowed us to easily check out Boston, Newport and several Connecticut spots...including a winery & brewery only 10 min away! We also enjoyed down days simply relaxing at Erin’s place….by the fire, lounging by the water or taking a paddle around the lake. And anything you could think of they had…sweatshirts and blankets for outside by the fire, games, fully stocked kitchen for making meals in, steam shower, office space, and more. Our family of four (with adult children) had plenty of space to spread out and have time for ourselves, too. I also really like the mid-century modern decor…very nice touch :) Erin and Jaiden were great hosts. They were very responsive and provided detailed instructions and ongoing communications to ensure our stay was going well. Thanks again!

Memorial Day weekend was cloudy, cool and windy, so my husband, elderly mother and I were especially pleased to have a nicely appointed and welcoming home base for hanging out. From a large screen TV down to the smallest of decorative details, Nicole has thought of everything to make for a relaxing stay. Having rented other places, I particularly appreciated spotless cookware, new bath towels, comfortable beds, and to top it all off an espresso machine! My tea drinking husband kept the electric tea kettle warm all morning. All this and a very nice, peaceful water view with great bird watching. We look forward to returning.

wonderful stay by the lake in Ashford! Joe is a very nice host and very responsive if needed.

Michael was fantastic with communicating with us, letting us know his expectations of us and giving us recommendations. We would highly suggest Michael and his home to anyone

What a gem of a place! Perfectly located to our daughter’s boarding school. We spent both parent’s weekends and graduation here, staying with multi-generations of our family. It has enough space in the great room for a small gathering. Just a wonderful spot that we highly recommend.

We stayed at the Bungalow for two weeks. It is super cute and cozy and obviously a lot of care has been taken to set it up for use. We had everything we needed for a long stay. Lots of dishes and pots and pans, even a toaster and an electric kettle. The brand-new stove was far nicer than most rentals. Even the fridge was above average. Overall, everything was clean and bright and pleasant. And great communication with the host from the time of booking to after checking out.

 We happened to stay during a short heatwave and the wooded location meant the cabin did not heat up very quickly, but when it did, the modern central A/C was very effective. Also, the windows are brand new and it was super quiet the whole time we were there. Even though there are other houses and possibly a rooster nearby, the cabin itself was completely quiet. I could barely even hear the A/C when it came on.

This place exceeded expectations for a cabin in the woods.

Amazing experience staying here. I will love to come back!!!

The house was beautiful with a wonderful view.

Such an amazing place to stay - easy to get to surrounding towns and local attractions but the physical location and the space lends itself to such a beautiful tranquility and peace we could feel ourselves relaxing the minute we got out of the car. Everything we could have wanted was provided, including a washer and dryer, the beds were so very comfortable, and being able to soak in the hot tub beneath the stars after a long day was just an added bonus. We were so grateful to be able to be in this space for about a week and hope to be able to rerun in the future!

Michael is a wonderful host and his home is lovely. Beautiful surroundings and view of the pond. This location is great for anyone who is looking for a peaceful retreat. Any time we had a question Michael was on it! We are from Boston but were visiting family during the holidays so we know the area. In the summer there are water sports and we watched people skating on the lake while we enjoyed coffee inside. For those not familiar with the area there are loads of places to explore, such as Old Sturbridge Village, the Brimfield Flea market and the Worcester Art Museum all within 20 minutes in any direction. Thank you Michael for being such a great host!

Had a wonderful stay at Mighty’s house on the lake. It was such a peaceful and beautiful area. The house was clean and tidy with a spacious bathroom and comfortable bed. It was reassuring to have our hosts right next door but there was a good amount of privacy. We enjoyed the fire pit in the evenings, taking the canoe out on the beautiful lake and having some space and time to wind down. I highly recommend this home for anyone looking to step away from life for a little while.

We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

We had an amazing girls' getaway at this lakeside house in Wales! The cozy living rooms both upstairs and downstairs were perfect spots for quality time and dinner together. We loved relaxing by the fire pit and enjoying the beautiful lake views. Paddle boarding/ and boating was definitely a highlight. Such a peaceful, charming spot.

We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!