Choosing a fitting accommodation is one of the most important aspects of designing a great trip, no matter where you’re venturing to. If you’re planning a vacation to New England this year, ditch the run-of-the-mill hotels and motels for something outstanding. There are a host of unique places to stay in Connecticut that can subsidize your adventure with charm, luxury, or quirky amenities. From boutique hotels to treehouses and yurts, we’ve scoured the internet reviews for these unique destinations that are sure to be a hit with your crew. After all, this is the 21st century, people! There’s so much more to a fabulous stay than a swimming pool and free Wi-Fi. Let’s find something with a bit more pizazz!
Roam Connecticut with us!
Connecticut exudes a luxurious vibe in its perfectly curated beach towns, but it also boasts vibrant cities that are easily manageable and a joy to explore. From Bristol to Bridgeport, Mystic to New Haven, we’ve explored it all, and we’ve crafted some pretty stellar adventures, too! From sightseeing scavenger hunts to urban art walks and bar crawls, we’ve covered every corner of “The Constitution State” so no matter where you roam, you can do it with us! Check out our full array of Connecticut hunts and make some time in your itinerary for a little adventure!
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Never considered Connecticut for a vacay?
If you’ve never experienced the magic of Connecticut, you may be wondering what we’re on about. Let us fill you in. First of all, Connecticut boasts some of the most amazing fall foliage in all of the country and draws visitors from all over the world to revel in its glorious golden hues. It has picturesque beaches, one of the highest-rated aquariums and sea museums in the states, historic lighthouses, a fantastic wine trail, excellent campgrounds, great mountain biking, and superb museums. It’s a small state that’s big on attractions and worth a visit for any type of traveler!
Unique Places to Stay in Connecticut
Now that you’re on board with Connecticut’s awesomeness, let’s get to the point and find you an accommodation that ticks all the boxes. Luxury hotels are nice and everyone loves a quaint bed and breakfast, but we’re going to focus on spots with more unique rooms, quirky personalities, and epic locations for this one. You might as well have an accommodation that’s as unique as you are!
1. The Griswold Inn
Opened the year of our independence cry, The Griswold Inn is considered one of the oldest continuously operating hotels in the country. Since 1776, its 33 rooms have made guests feel at home. The hotel has been continually updated over its long history, so you won’t be short on modern amenities, but it still retains that class historic inn vibe. Each historic room has a distinct character, no two are alike. Some have fireplaces, and some have water views. All have period reproduction furniture and Leonard’s Beds (the same Leonard’s that made the beds for the Whitehouse).
Aside from adorable guest rooms, The Griswold has three separate dining options. You can book a seat in the historic dining rooms where Chef Toppin serves up housemade desserts and traditional American fare. The next night, visit the Wine bar, where Chef Bond creates innovative tapas and macro plates that perfectly pair with the award-winning wine list. Then, take a seat at the Tap Room, where Chef Toppin’s team throws out the classic, but elevated, bar far with homemade burgers, fish ‘n’ chips, and local chowders.
Griswold Inn lucks out with the perfect location, too. Located in Essex Village, it boasts Connect River waterfront views, easy access to the Essex Steam Train & Riverboat, and the chance to visit Gilette Castle State Park.
Explore daring naval adventures, intriguing war history sites, and a unique Turtle submarine on our “Essex Scavenger Hunt.” Together we’ll find the clues, solve the riddles, and rack up points to hit the top spot on the city leaderboard. It’s an adventure your whole crew will love!
2. Winvian Farm
Winvian Farm, in Litchfield Hills, is a fantastic vacation destination in and of itself. The 113-acre farm features several unique accommodations ranging from a rustic lodge to numerous fun cottages, a campground, and a one-of-a-kind treehouse. The Treehouse at Winvian is a 780-square-foot beauty that’s suspended 35 feet off the forest floor. It features two gas fireplaces, a steam shower, and a jetted tub. The funky architectural design feels like it’s out of the pages of Dr. Seuss, only with an elevated and luxurious feel. The first floor features a king-sized bedroom, and the second floor has a full bar, a large viewing deck, and a swanky lounge.
Winvian also caters to its guests with excellent on-site restaurants. Enjoy a meal by the fire in the 18th-century dining room where Chef Chris Eddy’s Farm-to-Table Menu is loaded with fresh, seasonal dishes with ingredients from local farms. If you prefer a light meal, head for the new Maggie’s Tavern where bartender Chris Kamenos will whip you up an herb-infused cocktail to make your day, and you can munch on a deluxe charcuterie board with local artisanal cheeses. They’ve transformed the old game room into a swanky yet comfortable tavern with solarium seating. It’s the ideal place for a delicious lunch.
3. The Helicopter Suite
As a Winvian Farms exclusive, the Helicopter is one of the most unique spots on the list. It’s a fully renovated 1968 Sikorsky HH-3F Pelican that is situated inside one of their lovely cottages. It features a modern sofa, a flat-screen TV, a cocktail cockpit, and a theater in the fuselage. The room surrounding the chopper has a king-sized bed and plenty of space to spread out! Plus, you get all the other amenities of Winvian mentioned above!
4. Chic Farmhouse
Step back in time to this newly renovated farmhouse from the late 1800s. Surrounded by pastures with grazing horses, you’ll rest your head in an elegantly rustic home with four bedrooms and three large baths. The house features a chef’s kitchen, large en suite baths with jacuzzi tubs and walk-in showers, and an ideal location. It boasts every modern amenity with a contemporary and warm design.
The home is 3500 square feet and features ample living and hangout space. The dining space sits 12 people. It can sleep up to 12 comfortably, as the bedrooms have queen beds, and one room has two beds. There’s also a large front porch with sweeping views that makes the perfect outdoor hangout space.
Just 18 miles from Mystic, two miles from Foxwoods Resort Casino, and seven miles from Mohegan Sun Casino, you can spend your evenings playing crabs and slinging cocktails and then awaken (as late as you want) to the quiet ambiance of a country homestead. With a full laundry room, ample space, and an optional housekeeper, this home is the perfect spot for a family reunion or a large family getaway.
5. The Lighthouse Suite at Saybrook Point Inn and Spa
Located in Old Saybrook, the Lighthouse Suite at Saybrook Point Inn and Spa has been voted “the most romantic place to stay in Connecticut” by Connecticut Magazine. It’s a 900-square-foot suite on the tippy top of a tower with a private balcony offering sweeping views of Long Island Sound and the Connecticut River! It has a full-furnished kitchenette, a large seating area with floor-to-ceiling windows, and a comfortable sleeping quarter. Aside from this suite, the resort also offers several charming guesthouses and villas, all congregated around the marina.
With a traditional dining room, Fresh Salt outdoor restaurant, the Choo Choo Lounge, and Marina Bar, you won’t go hungry or thirsty at Saybrook Point. Saybrook features indoor pools, heated outdoor pools for year-round enjoyment, and a fabulous fitness center. It also boasts full spa services including a sauna, steam room, massages, and therapeutic whirlpool. As you might imagine, the rooms and services at Saybrook Point Inn do not come cheap, but they do come deluxe!
Check out “Say-Brooke’s Seaside Scavenger Shuffle” for a rousing good time exploring Old Saybrook.
6. Delamar Greenwich Harbor
Traveling with Fido? No worries, Delamar at Greenwich Harbor will accept your whole family, including the four-footed, furry ones. They don’t just allow your pooch to stay either. They pamper them as they deserve. The hotel offers grooming, dog walking, and playtime activities as well as plush beds, special bowls, and mineral water for each pet.
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It’s not all about the pets though, Delmar Greenwich Harbor also features special touches for the people including a stunning library with a large fireplace and exquisite artwork. Like all of Delamar’s luxury hotels, the Greenwich location includes a deluxe spa, an on-site restaurant, and all the high-end amenities you can ask for.
Greenwich is blessed with several beautiful museums, a few lovely beaches, fantastic theatre options, high-end shopping and dining, and numerous boat charters to choose from. You’ll find no shortage of fun activities in the area to keep your crew entertained.
7. Private Connecticut Island
Want to truly get away from it all? How about a stint on a private island? Located in Stoney Creeks on Thimble Island, Karen’s Airbnb is a place for respite. Her waterfront home is perched high on a granite rock affording it impeccable views. The house is four-bedroom, two-bath and fully furnished. Though the home is large and modern, there’s a twist. There’s no electricity or internet. The home is propane powered, so you’ll be truly relaxing away from social media distractions and work. The home sits on a large green grass lot with shade trees, almost fully surrounded by water, creating an ambiance sure to replace your lost screen time. While no electricity might turn some visitors off, the ones who have booked Karen’s place give it rave reviews!
The archipelago is located in Long Island Sound near Branford. You’ll arrive on the island by the Thimble Island Ferry or a water taxi from Stony Creek Harbor. There’s also a private slip and dock if you want to arrive by personal vessel. If you are looking for a true getaway from everything, you cannot beat having your own private island in Connecticut.
8. Geodesic Dome
Oh, the irony! The fancy private island home doesn’t have internet, but the rugged, one-room, Geodesic Dome in the pine forest has 55Mbps… what a world! Anyway, to be fair though, that’s all it has in the way of modern amenities. Robert’s Airbnb dome is a place to completely unplug in nature. The dome is a unique tiny house with cedar shake construction, located on a farm in Bethlehem, CT. It has no electricity, air conditioning, or heat, but the dome is located just outside the owner’s house, and guests have access to modern amenities through a door in their basement. It might sound weird, but the almost 300 guests who have called it their temporary home agree that it’s awesome.
The dome is small, just 165 sqft, but it’s constructed with wood from the property, so it fits right into the surroundings. It features a wooden ceiling, a skylight, and a comfy double bed. There’s a propane grill and a fire pit, so you won’t go hungry—especially since you’re on an organic farm! The owners are glad for you to wander the 65-acre property, help out with picking crops, or take a taste of some fresh produce. Join them on a tour of their working farm if you want. At night, nestle around the fire pit or enjoy a game of pool in the basement space that’s set aside for guests.
This spot is perfect for young couples looking for a romantic getaway. It’s an extremely budget-friendly version of Connecticut camping, and you have a plush bed and full bathroom facilities just a few feet away. It’s definitely a proper camping experience but with a few extra perks!
9. Nature and Luxury at Lavender Lake
Alright, let’s move far, far away from the rustic glamping sights and back to civilization. You’ll want for nothing in Ori’s six-bedroom, 11-bath Lavender Lake Estate. The home is nestled in the rolling hills of Woodbury Hamlet and has a private and serene setting. It feels open and airy with soaring exposed beam ceilings, massive windows that let in plenty of natural light, and incredible views of the surrounding landscape. The space also features a fully stocked and large kitchen, a dining room with a table to seat 12, extra counter seating, and two separate living rooms. It’s a contemporary open layout with plenty of space to move about with a large family or group of friends.
The home is a playground… literally. For adults, there’s a ping-pong table, giant bean bags, a 75’ theatre setup, a pool table, foosball, board games, etc. For the kiddos, this place is heaven. There’s an indoor trampoline and a basketball hoop. If you have 20-foot ceilings, you put in an indoor trampoline. Those are the rules.
Outside, the owners have installed a swing set and playground, sandbox, and multiple maintained hiking trails on the property. There’s a lovely herb garden you are welcome to partake in, and the jewel on the crown of the property—the 160’ swimming pond. The pond is manmade with a filtering stream that runs through it, keeping the water crystal clear and perfect for an afternoon swim! The home is equipped with kayaks and a SUP for extra pond fun. When the cold water gets overwhelming, just transfer to the hot tub, the heated swimming pool, or the connected heated jacuzzi spa. This magnificent home truly has all the amenities of the best hotels, but it’s all yours to enjoy with your crew!
10. The Inn at Stonington
The little borough of Stonington screams Nantucket vibes. The historic inn at the heart of the village is consistently rated as one of the best places to stay in CT. The inn features 18 individual guest rooms, each with its own personality and character. The rooms feature luxury linens and private balconies with views of the village and Fishers Island Sound. You’ll drink your morning coffee by the fireplace and finish your evening in the oversized soaking tubs. The inn serves a large continental breakfast with everything you could ask for, and in the evening they offer complimentary cheese and wine receptions in the luxurious first-floor dining room with views of the water.
The borough itself is a fantastic spot to be located. Commercialism has somehow escaped this little corner of the coast, and the village still retains its 18th-century charm. The town and inn have been featured in a few films, including Hope Springs with Meryl Streep and Tommy Lee Jones. It’s home to one of the last fishing fleets in Connecticut, so you can still watch lobstermen and yachtsmen put on the waters in the early morning and bring in their catch from your balcony.
The inn is within walking distance of excellent restaurants, boutique shops, and fantastic coffee shops in the adorable downtown area of Stonington. It also features easy access to the Mystic Sea Aquarium and Historic District. If you’re looking for a return to the true bed and breakfast vibe, The Inn at Stonington fits the bill!
11. The Mystic Yacht
Ahoy mateys! All aboard Mystic’s only VRBO yacht rental—Mystic Grace. What better place in the world to stay on the water than in a historic shipping town? The 1986 DeFever Yacht features three berths to sleep six people, 1.5 bathrooms, a full galley kitchen, and a dining nook. There’s a large soaking deck and two salons for lounging. Mystic Grace is heated for the winter and cooled for summer too!
The upper salon features a TV, refrigerator, and pull-out couches for lounging. The Main Salon, below deck, features another large sofa, stereo system, and TV. The forward cabin features a full-sized bed and half bath. The port-side bunk room has two single beds and a small work area. The stateroom features a queen-sized bed, full bath, vanity/desk, and a smart TV.
Mystic Grace is docked in the Mystic Downtown Marina. There’s parking at the marina, and it’s the perfect location for strolling the town on foot. We can’t think of a more Connecticut-appropriate stay than spending your vacation on a yacht!
Explore Mystic with us! From whaling ships to steam engines, we’ve got all your shipmate dreams covered on this adventurous sightseeing hunt through the heart of Mystic Seaport!
12. Willington Treehouse
Back to the canopies we go, with a stunning, modern treehouse on Bluebird Farm in Willington. Located just 20 minutes from Hartford, Bluebird Farm feels a world away. Surrounded by forest and a working farm, the space is completely serene while boasting easy access to nearby wineries, breweries, and antique malls of Willington.
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The house is captivating and custom-built. It’s a modern oasis in the sky with a spacious design. From your plush memory foam bed, you’ll be surrounded by panoramic views from the wall of windows. The cabin isn’t large, just one bedroom and one bath, with a small kitchenette, but it has everything you need for a comfortable stay. It has a cozy living room, a large viewing deck, and a grassy outdoor space with a fire pit and a gazebo. The treehouse has strong WiFi and a working bathroom as well.
Best of all, the treehouse is on a working animal farm, so with a tour from the hosts, you can go pet the Babydoll sheep, pigs, and goats! There are some small hiking trails on the property too. The surrounding area has some of the most antique shops in the state, and there are some pretty fantastic local vineyards to tour as well. The home is just a few minutes from the UCONN campus as well. A modern treehouse, on a 40-acre farm, surrounded by baby goats, and just minutes from shopping and fine wine… no wonder this place has almost perfect reviews!
Explore Hartford with Let’s Roam
When you’re ready for a taste of civilization again, pop into the capital and enjoy “The Riches of Hartford Scavenger Hunt.” Did you know that Hartford was once the richest city in the United States? This was in large part due to the Industrial Revolution and Hartford’s key role in it. On our city adventure, we delve deep into the past of the historic city. We explore Wadsworth Atheneum, Connecticut State Capitol, Old State House, and much more on a combination of historical sightseeing out and playful competition. You’ll follow the clues, solve the trivia and riddles, and gain points along the way to see how you match up against our Hartford city leaders. We have a good feeling you’re going to take the top spot!
13. The Whaler’s Inn
Another trendy hotel in Downtown Mystic, The Whaler’s Inn is a unique hotel in that it’s comprised of five separate buildings from different historical eras, so a walk through the complex is like walking through a time warp. The Main Inn features 14 guest rooms and hails from 1920. The historic structure was once known as the Clinton Building and was home to a Ford Model-T showroom on the ground floor, and housing for rent on the second and third floors. The space was converted into a hotel in 1969.
The 1865 House was the home of a prominent mystic shipbuilder. The Hoxie House was built in 1818 originally, though it has twice been destroyed by fire and rebuilt. Its owner had the vision of turning Mystic into a luxury summer resort spot, so he constructed the first luxury hotel in the town. Rounding it out, the Stonington and Noank Houses were built in the 1980s to accommodate the growing number of travelers to Mystic. Even across the five structures, there are only 45 guest rooms, so the place still feels intimate and cozy.
Aside from five different accommodation styles to choose from, The Whaler’s Inn also offers a fantastic dining experience. Pull up a seat at The Shipwright’s Daughter and splurge on the perfectly curated menu of lead chef David Standridge. Their five-course small plate tasting with wine pairing is one of those meals that you talk about for years to come!
14. Cottage by the Sea
It wouldn’t be a very good Connecticut accommodation list without a traditional cottage by the sea. This adorable cottage in Fairfield is hosted by Great Gull and has near-perfect ratings on Airbnb. It’s been newly renovated and is just steps from your very own private beach! Just imagine, leaving New York City, and within the hour, you’re resting in a hammock overlooking Long Island Sound!
The cottage is newly renovated but retains its shabby chic feel. The space consists of three bedrooms with one double, one queen, and two twin beds. The living space is open concept with a flowing dining room, kitchen, and lounge area. There is also a windowed porch overlooking the sea for afternoon drinks or morning coffee with a view. The home is outfitted with traditional beach decor, but trendy and chic. It’s a comfortable space to live, work, or play in.
If you’re having a working holiday, the owners of the property have partnered with B@Work Coworking space, a multi-level workspace just three miles down the road. It features waterfall and lake views, and guests of the cottage have free access to utilize the facilities. The cottage also has a dedicated workspace. Just make sure to take some time to relax with your toes in the sand! You have a private beach, remember?
Need a little help exploring Fairfield? So glad you asked! We’d be delighted to help!
15. The Study at Yale
Part of the Bespoke Hotel Line, The Study is a trendy hotel located at the heart of Yale University’s campus in New Haven, Connecticut. As you would expect from the name and the location the hotel features a design based on literature, art, and music. Unique photos of the campus by photographer Michael Marsland, adorn the walls, giving it a nostalgic and cozy feel.
The Living Room of the hotel is a communal gathering space, reminiscent of a dorm, featuring plush loungers, daily periodicals, and a mesmerizing floor-to-ceiling bookcase stocked with the classics. The book collection is sure to please, as it was specially curated by the staff at Strand Book Store in NYC. Next to the lounge, you’ll enjoy the cafe with a vast assortment of hot drinks and homemade pastries.
Heirloom Restaurant and Lounge is on-site serving up seasonal farm fresh and local seafood cuisine. There’s even a small art gallery to peruse. Aisling Gallery is an intimate collection of works by former and current Yale students.
The hotel consists of 124 guestrooms, including eight Study Suites and one Presidential Suite. Many of the rooms boast large windows with views overlooking the historic campus architecture. A stay at The Study is a pretty unique experience. While the rooms aren’t cheap. They aren’t insane either, given the location and nostalgic quality of the stay. A typical double room costs around $299 a night. So, you might not have been able to attend Yale, but it doesn’t mean you can’t pretend for a night!
Check out our Yale and New Haven scavenger hunts!
The Best Things to Do in Connecticut
Although your accommodation is going to be stellar with any of these options, you’ll need to pry yourself away from the view and go do a little sightseeing on your Connecticut adventure. Here are a few must-see spots for your trip!
- Take a tour of the Yale Campus. It’s incredible. Founded in 1701, it’s the third oldest campus in the country and features lovely galleries and museums to peruse.
- Tour the Mark Twain House & Museum for a glimpse into the life of the famous writer.
- The Mystic Seaport Museum and Aquarium and some of the best-rated maritime sights in the country. Go check them out!
- Wander the ruins of the home of legendary stage actor, William Gillette, in Gillette Castle State Park. The hiking trails are along old railroad tracks, and the views are phenomenal. Plus, there’s a crumbling castle!
- Visit the world-class collection at the Wadsworth Atheneum Museum of Art in Hartford.
- Try your luck at a few of the famous casinos, then retreat to your unique accommodation for some solace!
Closing Thoughts
Connecticut might not have topped your list of vacation destinations, but it really has so much to offer, especially if you’re looking for some serenity. From a stunning coastline to beautiful fishing villages to serene cabins in the woods, the unique places to stay in Connecticut make it worth the trip alone. Some of these epic locations are just a short drive from Boston or NYC, so you can escape the madness of the big city and retreat to Connecticut for a day trip or weekend getaway in the countryside easily! Book your stay. Pack those bags. We’ll see you soon for some scavenger hunt adventures in Connecticut!
For more unique accommodations, check out our list of fun places to stay in California! From the East Coast to the West, we’ve got you covered with unique stays in almost every state on our Explorer blog!
Looking for a day trip from Connecticut? Check out our epic one-day itinerary for New York City! We’ve hit all the top spots, organized in an efficient and timely manner, so you get the best sights, sounds, and tastes of NYC in one whirlwind of a day!
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