Book a Cabin in Windsor, MA

Select from a fantastic variety of comfy cabins near Windsor from $322 to $652 per night. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Book a great cabin in or around Windsor from $322 per night. This was the lowest rate offered in the last seven days. Prices reflect current offers and availability is subject to change. Additional terms may apply.

With 288 properties to choose from in and around Windsor, Travelocity makes it a breeze to plan your next great adventure. More than your usual hotel experience, places like Private And Artistic Cabin, Pet Friendly and This Is It Fabulous Vermont Cabin W offer a cozy stay with plenty of charm.

In the middle of nature yet intimate and cozy, Windsor cabins are excellent bases for traveling families. Lock in one of our cheap cabin rentals and spend your trip chasing adventure.

• Top of the list of family attractions to enjoy is Yaddo Gardens. From Windsor, it’s around 85 mi away to the northwest and a superb spot to spend time together.
• Rally the troops and head out to Kaaterskill Falls. This attraction is about 90 mi to the west of Windsor.
• Lastly, Equinox Preservation Trust is around 75 mi to the north of Windsor. It’s an excellent place to keep the kids occupied and make some nice family memories while you’re at it.

There’s nothing like heading for the mountains to make you feel revitalized and on top of the world. Soak up picturesque natural views and recharge your batteries at one of these Windsor mountain cabins:

• Cabin - Charming, Quiet, River Front is a terrific base for a scenic mountain vacation. Stay a few nights and enjoy amenities like snowsport activities and skiing facilities.
• Alternatively, soak up the mountain lifestyle at This Is It Fabulous Vermont Cabin W. It comes with a wood stove, winery tours and much more.

Wake up every morning to picturesque water views and the sound of birds twittering when you stay at one of these Windsor cabins by the river. From charming rustic retreats to spacious luxury cabins right on the riverfront, we know you’ll find one you’ll love.

• Cabin - Charming, Quiet, River Front — Book a few nights at this comfy riverside retreat and let all your troubles drift away. Amenities like snowsport activities and skiing facilities help make this place a popular choice with vacationers.
• Cabin - Romantic Retreat — With on-site watersports, snowsport activities and loads of other amenities, this cabin has all you need for an unforgettable stay.

Pack your swimsuit and inflatable ring. A Windsor cabin with a pool is the ultimate escape, mixing comfort, nature and a splashing good time! Jump into one of the following options:

• Lock in a stay at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. There are lots of convenient amenities here including a swimming pool and a porch.
• Another desirable stay is Cabin - Romantic Retreat. As well as an enticing pool, you can take full advantage of on-site watersports and a swimming pool.

Wake up and be steps from beautiful blue waters when you stay at one of our Windsor beach cabin rentals. Whether you want to have fun in the ocean or simply laze on the shore, your beach cabin escape will be one to remember:

• Enjoy a taste of real coastal living at Cabin - Relax, Reconnect And Enjoy. It has everything you need for a vacation near the sea, including on-site watersports and children’s activities.
• Or, enjoy your seaside escape at Lakefront - King - Petsok - W And D. This comfy cabin offers on-site watersports, clothes washing facilities and much more.

Getting your hands on the perfect Windsor cabin is easy with Travelocity. Step 1: Enter your destination, dates and number of travelers. Next, use our handy filter tool to narrow your search. Finally, reserve your favorite option and get packing! Think your plans might change? Choose a cabin that offers free cancellation. Booking with Travelocity means booking with confidence. Find the same property cheaper somewhere else within 24 hours and we’ll refund you the difference. That’s Travelocity’s Price Guarantee.