Tiny house holiday rentals in Connecticut

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Value · Family · River

New! “LaBoDee”

“LaBoDee”, a fun play on the word abode, house, is a tiny cottage located central to CT’s unique shoreline communities, just off I95. “LaBoDee” is one room with a fully equipped kitchenette, ready for those who would like to stay awhile. “LaBoDee” is on a property contiguous to a state forest (a trail is right outside the door) yet within walking distance is a delicious deli, market, gas station, pizza, a lake, and close by is the beach. A local restaurant has day passes for their beach- $20!!

Family · Value · Accuracy

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Family · Location · Condition

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Family · Value · Breakfast

Wizard's Roost at Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

Location · Family · Walkability

Vinola-Lakeside Cabin on Beach Pond with Sauna

Vinola is the "Cabin in the Woods" you've been looking for! Enjoy an idyllic escape from the city year-round. Activities include swimming, fishing, hiking, kayaking or just a cozy snooze with a book on the couch. Top off your stay by trying our traditional wood-fired Finnish sauna. Relax tired muscles and rejuvenate the soul. Private beach and lake access on Beach Pond just 335 feet from the cabin. Check our photos and reviews! Our guests consistently remark that one night isn't enough.

Family · Location · Pool

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Location · Family · Accuracy

1 Bed Pond Cottage w/ pool/hot tub/sauna access

Adorable & cozy cottage sits on the pondside corner of our 25 acre property. Deck is great for BBQ and stargazing at night. Enjoy fire pit on the beach for s’mores. Pool not heated but hot tub can be heated. Sauna in gazebo. Enjoy the canoe and fish in our private pond (carp & bass) Lots of hiking trails nearby and great restaurants. 20 mins. from Harlem-Valley Wingdale train station. Car is highly recommended as taxi service is limited.

Value · Family · Air conditioning

Little Lake Cabin— Lake Access, Hot Tub & Kayaks

Named one of Connecticut's best Airbnbs by Business Insider, The Little Lake Cabin is a cozy wooded retreat near Candlewood Lake. Guests enjoy access to the lake and marina, plus kayaks for exploring the lake. Relax in the year-round hot tub, gather around the fire pit, and unwind under the stars. Close to hiking, wineries, skiing, boating, antique shops, and charming New England towns...perfect for couples getaways and lake escapes.

Family · Location · Condition

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Value · Location · Pets

Come to the woods and snuggle in front of the fire

Come to the woods of Southeastern Connecticut and enjoy some solitude and connection in the woods while wrapped in our flannel LL Bean bathrobes. Snuggle with a glass of wine or coffee by the fire and unplug, rest, and rejuvenate with your partner or by yourself. Only fifteen minutes away from casinos, shopping or restaurants in Mystic or downtown Westerly, RI.

Location · Family · Sleep quality

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Family · Value · View