9 Best Airbnb Connecticut Vacation Rentals: Boats, Treehouses, & More

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Wherever I travel, Airbnbs remain some of my favorite places to stay. Ranging from treehouses to sailboats, yurts to condos, Airbnb properties are extremely unique, comfortable, and fun. It’s not like staying in a cookie-cutter hotel, that’s for sure. 

When visiting Connecticut, you should absolutely consider booking an Airbnb. There are hundreds of amazing options to choose from, but I’ve rounded up 9 super unique and attractive choices here: 9 exceptional Airbnbs in Connecticut.


Direct waterfront beach cottage – Milford, CT

Photo via Airbnb.com

Many visitors to Connecticut are coming here for the magic of the coast. If that’s you, you should absolutely check out this cottage that is located right on the beach. This adorable Airbnb is able to accommodate up to 6 guests in 4 bedrooms. 

You will love the views over Long Island Sound from the cottage’s porch. The private beach is a calm, lovely spot to relax or play with family and friends.

READ NEXT  15 Best Beaches in Connecticut


Water Forest Retreat Octagon – Norwich, CT

Photo via Airbnb.com

This is a unique tiny house in CT in the woods that will make for an awesome stay. Two guests seeking a rustic retreat into the seclusion of nature should consider this space. Set on 100 acres of forest, you’ll be surrounded by a watefall, marsh, pond, and hiking trails. The ideal spot to get away from it all.

The tiny house/cabin itself is a private 144 ft.² electrified and heated cedar octagon located next to Goldmine Brook. There is lots of outdoor space to enjoy, but you’ll also be very comfortable in this nicely-decorated octagon. Note: there’s no running water/plumbing at this property; it is indeed a rustic retreat. 

PS: This Airbnb is located in Norwich, about 30 minutes’ drive from Mystic, a destination I definitely recommend exploring.


Stay in a Tiny House on our Sustainable Farm! – Guildford, CT

Photo via Airbnb.com

Who wouldn’t want to stay in this adorable Connecticut tiny house Airbnb?! I certainly want to! Tiny houses are all the rage right now, and this one is no exception. Make sure to click through to the listing and look at all the photos. What a nice space. 

Tiny houses can be surprisingly spacious, but there’s not room in there for more than 2 guests. That makes this a nice option for a romantic getaway for a couple. 

Located on an 8-acre sustainable farm, this is a perfect place to relax or to jump in and learn about farming! 


The Spirit Horse Farm – Kent, CT

Photo via Airbnb.com

I can’t get over the look of this place. It’s got a sort of country-western vibe mixed with classic New England charm. And best of all, it’s a horse farm!

According to the listing, there is “something for everyone at The Spirit Horse Farm!” This includes that rescue horses, which, though not always onsite, are happy to stand for a photo with guests. The lush land is filled with more wildlife/animals, including peacocks and white doves. While the outdoor experience is undoubtedly magical, you will be kept busy inside as well: there are billiards, ping-pong, a full gym, garage band style musical equipment, board games, and much more. 

Up to 14 guests can be cozy at the Spirit Horse Farm, located in Kent, CT in the Litchfield Hills region.


Escape to a Restored New England Antique Milk Barn – Bethel, CT

Photo via Airbnb.com

Another unique Airbnb experience in Connecticut is found here at this antique milk barn. The photo above shows the property from the air, and it is obviously quite pastoral. 

An escape to the Connecticut countryside, here in Fairfield County, awaits you at the historic Benedict Barn Cottage. (Read the listing for more on the history).

Perfect for a couple or small group, this property can host up to 5 guests. With a pool and hot tub, this is an especially lovely option in the summer months. 


A Connecticut River Houseboat – Newtown, CT

One of the advantages of AirBnb is its numerous unique properties. If you’ve ever wanted to experience life on a houseboat, this pond-side structure in Connecticut will give you the opportunity.

A screened porch with 2 rocking chairs and a table surrounded by green trees
Photo via Airbnb.com

Located on the host’s property, this floating abode can house two guests in the midst of nature. This is a rustic space just around an hour from NYC, making it a great weekend getaway spot. There are other cabins on the same property and there are communal spaces such as the kitchen and firepits. Definitely a unique type of “roughing it.”


Water Forest Retreat Tree House – Norwich, CT

A platform bed with blue bedding in a bedroom with a window and a ceiling fan
Photo via Airbnb.com

Oooh, a treehouse! If you’ve never stayed in a treehouse, this one would be a beautiful choice! Also, it’s not super high up, so those with a fear of heights need not worry. 

This is the Water Forest Retreat in Norwich, set up for 2 guests. While you’re close to amenities and activities, this spot feels secluded and quiet-perfect for a Connecticut weekend getaway. 

The treehouse is 168 sq ft., heated and electrified, but does not offer running water. Surrounded by nature, you’ll love relaxing on the deck, catching the patterns of light from the two indoor stained glass windows, or enjoying the outdoors on over 2 1/2 miles of  nearby hiking trails. The Octagon Airbnb listed above is also in the same area/owned by the same hosts. 

Be sure to read the entire listing, as these hosts provide plenty of information and travel suggestions to guests!


Waterfront Joshua Cove Cottage with private beach – Guildford, CT

Photo via Airbnb.com

A perfect weekend getaway from New Haven, Stamford, or even NYC, this private and pretty cottage is situated on Joshua Cove with its own private beach. A bit of country meets coast, this Connecticut Airbnb just might offer the best of both worlds.

There is plenty to do in and around the cabin. Excellent kayaking, fishing, restaurants, and shopping are among the possibilities. Want to visit Yale University? It’s just 15 minutes away. An ideal location for your next trip.

The cottage accommodates up to 4 guests with a 1 bedroom and loft setup.


The Little Lake Cabin – near lake with hot tub – New Fairfield, CT

Log cabin in the woods at dusk
Photo via Airbnb.com

Don’t forget about all the warm and welcoming cabins in Connecticut. There are so many available through Airbnb and all of them have something special to offer.

For this one, the lakeside location and hot tub are a great addition, but the decor inside this cabin is absolutely lovely. Check out all the photos, or pop over to their Instagram. Honestly, I’m kind of obsessed with this place.

Just 90 minutes from NYC, this CT Airbnb cabin is the ideal getaway for s’mores under the stars, enjoying Squantz Pond, or simply relaxing with your favorite travel companion. 

Still haven’t found what you’re looking for? No problem. You can search all the best Connecticut Airbnb properties right from here:

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