How to plan romantic getaways at the most romantic places in CT

couple on the beach in CTLittle, unassuming Connecticut can be a surprisingly romantic place.

 

In fact, with so many diverse destinations crammed into this little state, it’s more a matter of deciding what sort of romantic experience you’re looking to achieve.

 

From a couples retreat in a cabin in the woods to a shorefront romantic destination, there are enough escapes throughout the state to host many a romantic getaway.

Most romantic weekend getaways in CT for couples

This guide to romantic places and getaways in CT is a bit of a choose your own adventure.

 

Pick your destination first from the list of the most romantic places in Connecticut.

 

Then, decide on which romantic restaurant to visit and place to stay on your trip, including options like:

  • Cabins
  • Cottages
  • Bed and breakfasts
  • Inns
  • Hotels

With the basic building blocks in hand, you can get more granular in your planning by looking at our list of date ideas in Connecticut, or leave the rest to fate.

10 of the most romantic places in CT

beach at milford, CTNo matter what time of the year, there is always a charming Connecticut town that’s perfect for a romantic getaway.

 

There are plenty of romantic places that didn’t make this list. While New Haven and Hartford are perfect destinations for art and culture fans, they’re a little too big to meet what Connecticut is most known for, romantically speaking: cute and quaint.

 

Milford, meanwhile, is absolutely adorable. But romantic places to stay nearby are a bit lacking, and the town is almost too small to spend more than a pleasant afternoon.

Greenwich & the Gold Coast of Connecticut

Close to New York, Greenwich and nearby towns like Westport offer a unique mix of cosmopolitan sophistication and rustic charm.

Greenwich

Greenwich is just a 40-minute train ride away from Grand Central Terminal, but its elegant yet bucolic vibe feels much farther.

 

There is a long list of things to do just in downtown Greenwich, depending on your interests. Greenwich Avenue’s trendy cafés and restaurants, plus luxury boutiques and shops, is a major destination for the entire area. Art galleries and museums like the Bruce Museum pack a cultural punch. Meanwhile, the hills of back Greenwich play host to diverse activities as polo matches and hiking on well-maintained nature trails.

 

Each of the town’s neighborhoods offer their own unique vibe, however, and each is worth exploring.

 

Be sure to download the Visitor’s Guide to Greenwich, CT, before you plan your visit.

Westport

A short ways up Long Island Sound from Greenwich, Westport is the most funky and avant-garde of the towns of Connecticut’s Gold Coast.

 

Global fare is in abundance throughout the town, though the biggest draws are its beaches: Compo Beach or Sherwood Island State Park.

 

Learn more about the shoreline or take a ferry to a local lighthouse at the Maritime Aquarium in Norwalk, or catch a play at the Westport Country Playhouse.

 

Finish-off the day at the astronomical observatories of either town before bedding down for the night.

  • Stanton House Inn offers an elegant, romantic getaway in a historic mansion close to downtown Greenwich
  • The Delamar Greenwich Harbor hotel is a luxurious boutique hotel, and is one of the few waterfront hotels in Connecticut, overlooking Greenwich Harbor
  • If you’d prefer a romantic cabin feel on your trip, snag a beautifully restored cottage from 1790 in Westport

Madison

couple relaxing on the grass while picnicking in ConnecticutThis cute beach town is a short drive east of New Haven.

 

Start a romantic escape here by perusing the stacks at R.J. Julia Booksellers with a great cup of coffee from one of the local cafés.

 

Spend a warm, sunny day at either the beach or cycling.

 

Hammonasset Beach State Park is the largest beach in the state. The panoramic ocean views and cool breezes makes this spot ideal for a beach day, complete with a picnic.

 

Alternatively, bike or walk the Shoreline Greenway Trail, which will stretch across much of the Connecticut shoreline once complete.

 

Before or after taking a late afternoon stroll, be sure to watch the sunset with a drink from the porch of the Madison Beach Hotel. It’s the only beachfront hotel remaining in Connecticut.

Essex & Chester

Another charming town on the list distinguishes itself by being a creative source for Stars Hollow, of Gilmore Girls fame.

Essex

Essex is also special for being one of the only towns in America occupied by a foreign power, the British during the War of 1812.

 

But the town rebounded from the attack, and remains both cute and historic.

 

Today, the streets are lined with buildings dating back to before the Revolutionary War, cute shops and restaurants. Foremost among them is one of the oldest taverns in America, which survived British occupation and Prohibition, the Griswold Inn.

 

A ride on the Essex Steam Train & Riverboat will give you an introduction to the mouth of the Connecticut River Valley. The area’s picturesque villages, marshes, and native wildlife led the Nature Conservancy to name it one of the last great places on Earth.

Chester

Just ten minutes up the road from Essex is a decidedly more rural and inland village. While Chester oozes quaintness, its small town feel keeps it charming.

 

The gift shops, cafés, and art galleries like Chester Gallery give the town its funky and artsy vibe.

 

But the local monument to eccentricity is just across the river in East Haddam. Take the Chester-Hadlyme Ferry to visit Gillette Castle State Park. This 24-room mansion built to mimic a medieval fortress by the original American actor of Sherlock Holmes is one of the most unique attractions in southern Connecticut.

 

Unwind with a show at the nearby Ivoryton Playhouse, the oldest continuously performing summer theatre in the United States, before heading back to your preferred romantic lodging.

 

Some nearby options include:

Mystic Country

These former seaports have done an amazing job of preserving the historic atmosphere of their towns.

Mystic

Cider mill outside of Mystic, one of the most romantic places for getaways in CTMystic is now a mariner’s dream destination.

 

Mystic Seaport is coastal New England’s version of Colonial Williamsburg, including historic ships open for exploration.

 

The Mystic Aquarium introduces visitors to a wide variety of sea life, including beluga whales and penguins.

 

Finish-off the day watching the sunset from the deck of the Argia schooner.

 

And there’s so much more to explore in Mystic and Stonington. Check-out our guide to the best activities, attractions, and things to do in Mystic, Connecticut.

 

Unwind at the end of the day at your choice of spots:

Stonington

Perched on a tiny peninsula jutting into Long Island Sound, historic Stonington is a perfectly-preserved former whaling town.

 

It’s now home to the only remaining fishing fleet in Connecticut, so the seafood is guaranteed to be fresh here.

 

Fortunately, the whalers are long gone.

 

And while many of its seafood restaurants are top notch, walking along the narrow streets of Stonington feels like a mix between Charleston, SC, and Nantucket.

 

The surrounding countryside offers gorgeous views of the bucolic scenery. Farm stands and some of the best Connecticut wineries on the CT wine trail line the country roads.

 

Little Stonington offers a delightful place for couples to unwind in the evening, depending on the vibe you’re pursuing:

  • Inn at Stonington is a classic New England Inn right in the heart of Stonington, as the name implies

 

Litchfield Hills

lake at one of the most romantic places in CT, ideal for romantic getaways in CTLitchfield County in the northwest corner of Connecticut offers the peaceful tranquility of the woods that many equate with much farther north in New England.

 

While this area is ideal for enjoying the best of Connecticut’s fall foliage, it’s also a hot spot for outdoor winter enthusiasts, too.

 

The small towns and verdant hills of the southern Berkshires are a destination for outdoor activities any time of year. And what’s better than relaxing in a hot tub or by an open fire after a long yet exciting day of exploring the wilderness?

Cornwall

Cornwall feels like a town that time forgot.

 

It’s most famous for its historic covered bridge, the only one in Connecticut. But the neighborhood that rises uphill from the bridge is cute and full of unique shops.

 

You and your significant other can pack a lunch to hike through the forest of Mohawk State Park. Make it to the summit to enjoy a 360-degree view of the surrounding mountains.

 

Mohawk Mountain is a perfect choice for skiers who want a variety of trail difficulties but don’t want to drive to Vermont, or even farther.

Kent

Are you looking for a little, funky town, nestled away in some of the best fall foliage in the state?

 

Then a visit to Kent is a perfect date idea for you.

 

The cute little town is hugely popular with New Yorkers with their own cars. The boutiques, restaurants, and ice cream shops lining the streets beckon the idle visitor.

 

But the surrounding scenery is the biggest draw.

 

Parks like Kent Falls State Park and Macedonia Brook State Park offer plenty of fresh air and wide open spaces to visitors.

New Milford

bridge at lover's leap state park, one of the most romantic places for getaways in CTOne of the largest towns in Litchfield County also features a quintessentially Americana feel.

 

Centered on its town green, it is the largest in New England. The surrounding downtown still has an old-timey neighborhood vibe to match the excellent dining, shopping and cultural attractions centered on Bank Street.

 

One of the biggest attractions are the surrounding lakes, especially Candlewood Lake, the largest in Connecticut. And Lake Waramaug is just to the northeast of the town.

 

Most Sundays of the year, the largest flea market in New England, the Elephant’s Trunk, gathers on the southern side of town.

 

But a particularly romantic hike is in town, as well. Lover’s Leap State Park is named for the site where a local Native American chief’s daughter leapt to her death with her English settler lover. The site is an easy hike and features such historical points as the Lover’s Leap Bridge, built in 1895.

Where to stay in the Litchfield Hills

Most towns throughout the county have cute bed and breakfasts and inns.

 

One of the most premier inns in Connecticut is the Mayflower Inn and Spa in Washington, a creative source for the inn of Gilmore Girls.

 

But it’s also the ideal location to book a romantic cabin for your getaway.

 

By the far one of the most unique places to stay in all of Connecticut features cabins and cottages scattered throughout the 113-acre property. Winvian Farm hosts guests in the most whimsical of cottages, from a helicopter to a treehouse.

 

A few of the most popular choices include:

Most romantic restaurants in Connecticut

Franke Pepe's pizza sign for a romantic restaurant in one of the most romantic places for getaways in CTVisitors often equate quaint and historic with Connecticut. But while some options for romantic dining fits that bill, others can be quite edgy.

 

Check-out our full list of romantic restaurants in Connecticut, but a few top choices range from French to historic taverns to noodle bars.

    1. Thomas Henkelmann
      Our standard recommendation for a romantic (albeit expensive) evening in Greenwich, this French restaurant is quite formal, but service and food are excellent
    2. Barcelona
      Of the several branches of this local chain restaurant, Barcelona in Fairfield is the best, with outdoor seating in the summer months and the opportunity to enjoy kitchen garden to table cuisine
    3. Mecha
      This noodle bar is another local chain, and any of its sites are splendid: Norwalk, Fairfield, or New Haven
    4. Frank Pepe’s Pizza
      Connecticut, home to one of the largest Italian-American populations in the country, is well-known for its pizza. And New Haven wins awards for it. Check-out the first pizza restaurant here, opened in 1925.
    5. Union League Cafe
      While Thomas Henkelmann offers more of a country French vibe, guests at Union League Cafe in New Haven will feel as if they’ve settled into a Parisian bistro. This is where locals impress their dates with a true dining experience.
    6. The Griswold Inn
      With fireplaces and warm and cozy seating, how could dining at one of the oldest taverns in America not be romantic? Add-on a stroll around Essex before or after a meal here.

Most romantic getaways in CT

Now that you’ve got a good idea of the vibe of your ideal destination in Connecticut, there’s only one major detail left to finish planning your getaway.

 

Where to stay?

 

Scroll below for hotels, inns, even cabins that offer amenities that lend themselves to romantic getaways.

 

Beneath this list is a more in-depth introduction to each of the places we describe.

A few romantic getaways with a jacuzzi in-room

couple enjoying a romantic hike in the woods of CTWhirlpool or JACUZZI® tubs in a room brings to mind the famously gaudy champagne glass tubs in the Poconos.

 

Luckily, Connecticut offers a more toned-down experience.

 

At least, that’s the case with the choices listed below.

 

For the full-on experience of a champagne tower suite, head to the Poconos for all the 1970s romantic kitsch your heart could desire.

 

This writer included locally-owned and operated properties, finding chain hotels with JACUZZI® or Whirlpool tubs is much easier.

  • Stanton House Inn has a 2-person Whirlpool tub in our Sackett Suite, tucked away on the top floor of the mansion, with beautiful views of the pool and surrounding gardens; a separate sitting area, and king-sized bed
  • Stonecroft Country Inn near Mystic offers spacious theme suites in the barn of this gorgeous countryside inn. Many of them have a 2-person tub in the bathroom
  • Winvian Farm offers interesting and unique accommodations in the center of Litchfield County. Regardless of which accommodation you choose, each includes a JACUZZI® tub
  • Saybrook Point Inn & Spa has JACUZZI® tubs in their villas
  • Inn at Harbor Hill Marina offers Whirlpool or JACUZZI® tubs in several of their guest rooms

 

If you’re looking for something a little more rustic, a few of the cabins and cottages we’ve mentioned offer JACUZZI® tubs:

Romantic getaways with fireplaces in-room

On a cold, wintry night, there’s nothing more romantic than bundling-up and staying close to your significant other by a warm fireplace.

 

And Connecticut has both cold, wintry nights and fireplaces in abundance!

 

A few romantic bed and breakfasts and inns with fireplaces in guest rooms throughout the state include:

Romantic hotels with fireplaces in their guest rooms include:

 

A few of the cabins that offer fireplaces among their amenities include:

 

Most inns and hotels only offer working fireplaces in colder months of the year, generally from October to March or April.

 

To be fair:

 

Why would you want a fireplace in the summer?

 

It’s a recipe for having to keep your air conditioning blasting just to keep the room tolerable, because profuse sweating is not romantic.

Waterfront getaways in Connecticut

lighthouse in old saybrook, one of the most romantic getaways and places in CTConnecticut’s shoreline is one of the most expensive resources in the state.

 

More so than any other type of real estate, they’re not making any more of it.

 

As such, much of the state’s coastline was purchased for astronomical prices by private owners to build their palatial estates.

 

Most of the CT shoreline hotels have long ago converted into private mansions, too.

 

But a few persist, offering romantic getaways with spectacular views of Long Island Sound:

  • Saybrook Point Inn and Spa offers a panoramic view of Long Island Sound and the mouth of the Connecticut River
  • The Inn at Stonington claims to be waterfront, which it is, on the opposite end of a parking lot. Sit in a chair or on the bed in your room and you can probably frame your view out the window of a parking lot-less water view
  • Inn at Harbor Hill Marina, as the name suggests, overlooks Niantic’s harbor
  • Steamboat Inn in downtown Mystic is as close as you can get to the Mystic River waterfront. So much so that guests can moor their boats right outside the inn if so inclined
  • Delamar Greenwich Harbor overlooks little Greenwich Harbor

Beachfront getaways in CT

Beach in Niantic, CTIn addition to the limited number of hotels on the coast, unlike some other states, Connecticut has strict laws controlling construction close to the coastline.

 

So hotels lining the beachfront are not to be seen here.

 

In fact, there’s only one hotel in all of Connecticut that is actually facing a beach, the Madison Beach Hotel.

A complete list of the most romantic inns, hotels, and cabins in Connecticut

With a solid handle on romantic amenities offered at your various choices throughout Connecticut, learn more below about your top pick:

7 of the most romantic bed and breakfasts and inns in all of CT

romantic bed and breakfast inns for places to plan getaways in CTThis writer can’t fully explain it, but there is a societal perception that romantic getaways are made at bed and breakfasts.

 

How many times has one of your co-workers mentioned going on a romantic trip to a cute, little, bed and breakfast somewhere in New England?

 

Perhaps it’s the pleasure of enjoying attentive hosts and innkeepers focusing on the cooking and cleaning while you luxuriate in a historic home and focus your attention on each other.

 

Luckily, you can achieve this at a location much closer than anywhere in Maine or Vermont, right here in Connecticut.

  1. Stanton House Inn

Brush Suite at the Stanton House InnFirst built in 1843, Stanton House Inn was a private home for almost a century before living several different lives and becoming a bed and breakfast in 1985.

 

As befits a former home, the inn offers a unique experience of staying in a former mansion in downtown Greenwich.

 

Our 20 individually-decorated suites and guest rooms offer varied amenities as:

 

That said, other major draws include our parlors, which offer ample space for spreading out and enjoying a good book from the library. Enjoy breakfast and afternoon tea in our dining room; and be sure to explore the romantic ruins in the back gardens after taking a dip in our seasonal outdoor pool.

 

And of course, our team that strives to provide that home away from home, bed and breakfast experience to our guests.

 

And everything here is within an easy walk in downtown Greenwich, even the train station to explore other parts of the state.

 

Be sure to download the Visitor’s Guide to Greenwich before you plan your trip! Our town is an easy 40-minute train ride from midtown Manhattan.

 

Add romantic weekend getaway packages to your stay to make your visit extra romantic.

2. Stonecroft Country Inn

Nestled away from the hubbub of Mystic on 6. 5 bucolic acres in Ledyard sits Stonecroft Country Inn. This inn features rooms in the historic farmhouse, as well as more recently-updated suites in the barn that include such features as fireplaces and whirlpool baths.

 

And the location is ideal for exploring Mystic, wineries, and the beach on a romantic getaway.

3. The Griswold Inn

If a historic location is your idea of romance, then it would be hard to beat The Griswold Inn’s level of historical significance.

 

It’s also hard to beat its location in the center of quaint and cute Essex.

 

This inn has been in business since the Revolutionary War era, and each of the 34 different rooms are furnished with antiques and period reproductions to add to the historic ambience.

 

Each room at the Griswold Inn offers different amenities, such as village or water views or fireplaces.

4. The Bee and Thistle Inn

walking along the beach in ConnecticutSituated in the charming village of Old Lyme, the Bee and Thistle Inn is in a historic mansion built in 1756 for Judge William Noyes.

 

The Bee and Thistle became an inn in the 1930s and has been hosting visitors to town in its opulent, colonial-style settings ever since.

 

Guests can enjoy a treatment at the spa, or a romantic meal at the restaurant on-site. All within easy reach of the artsy town of Old Lyme.

5. The Inn at Stonington

Right along the main drag of historic Stonington sits the Inn at Stonington.

 

While not as historic of a building as the others on this list, the tasteful decor and vision of the builders effectively create that colonial, historic, vibe that makes it an ideal place for a visit to Stonington.

6. The Inn at Harbor Hill Marina

As befits the old beach town on the train line between New York City and Boston, the Inn at Harbor Hill Marina is a wonderfully romantic destination in cute Niantic.

 

While the fireplaces and tubs are a delight, the most unique draw to this little inn are the balconies and views from the back lawn of the harbor and Long Island Sound beyond.

7. Steamboat Inn

Overlooking Mystic River, close to the Mystic Bascule bridge, sits Steamboat Inn.

 

The luxurious accommodations mixed with antique furnishings honor the industrial history of the area, a major former shipbuilding location.

 

Steamboat Inn offers guests the opportunity to both moor their boat at their wide dock out front and explore Mystic on foot.

6 of the most romantic Connecticut cabins

couple chopping wood before lunch at a romantic cabin in one of the most romantic places for getaways in CTFor a more rustic retreat where you and your significant other can rough it out a bit more, why not imagine yourself chopping wood to burn in your very own wood-burning fireplace at a lakeside cabin?

 

Or pick a more glamorous option, Connecticut offers both extremes of cabin and cottage rentals.

A cottage with lake views and a fireplace in Sherman

While this vacation rental lists itself as a cottage, it exudes a cabin atmosphere.

 

Two lake beaches, Green Pond and Candlewood Lake, are closeby, and you can enjoy gorgeous lake views from the deck of the cabin.

 

Top features include:

  • Fireplace
  • JACUZZI®
  • Gas grill
  • Full kitchen

 

This lake cottage sleeps up to 5 if you’re hoping to avoid intimacy, but it’s perfect for a romantic getaway.

Cozy, modern, forest cabin with a babbling brook in Cornwall

Although this cabin was built in the 1930s, it’s been extensively renovated and updated to create a modern space that’s Instagram-worthy.

 

The bright and airy cabin overlooks a private brook, and the noise certainly adds to a romantic forest retreat getaway.

A little cabin close to a lake with a hot tub in New Fairfield

Speaking of Instagram, this little cabin has its own Instagram account after the new owners did an extensive renovation.

 

The interior is Mid-Century Modern meets rustic backwoods cabin. And it works.

 

Scrolling through The Little Lake Cabin’s account was a major distraction from writing this article.

An A-Frame cabin off of Candlewood Lake in New Milford

A-Frame cabins are quintessential wildness for this writer, but it was surprisingly difficult to find many in Connecticut.

 

But this A-Frame in New Milford makes up for it, with a cabin designed in the 1960s by a Finnish architect.

 

The giant windows and free-standing fireplace add to the romantic and rustic yet modern charm.

A log cabin that looks like it came straight out of an old storybook in Colebrook

This log cabin can host up to 9 people, so a romantic getaway would provide ample opportunity to spread-out.

 

Or spend each night in a new bed?

 

And a billiards table in the basement and a hot tub on the porch are great touches at this storybook log cabin.

A cozy stone cottage out of the movie, The Holiday, in Granby

This little stone cottage, built in the 1930s, is dripping with rustic European charm in a quiet area formerly popular with the Hartford elite.

 

This charming cottage was the home of domestic staff for a wealthy family while at their country retreat.

 

Today, the cozy stone cottage features a huge stone fireplace and bath fixtures from the 1930s. What it doesn’t offer is a kitchen, so be ready to enjoy romantic Connecticut dining nearby!

Charming historic cottage perfectly kept in Westport

A historic cabin in beautiful Westport, this structure was built in 1790. It has recently been renovated to be a gorgeous country retreat.

The Top 5 romantic hotels in all of Connecticut

couple kissing at sunset in ConnecticutAs befits one of the wealthiest states in the country, romantic hotels in Connecticut take luxury almost to an extreme.

 

Almost.

 

Below are the top hotels for romantic getaways, spanning the state from the hills of Litchfield County to the coastline.

 

As with all things luxury, these places are a splurge.

Mayflower Inn and Spa

This luxury hotel was originally an inn that inspired the one in the Gilmore Girls.

 

Today, the elegant Mayflower Inn is part of the Auberge Resorts collection. Guests can enjoy many first-class amenities on its 58 acres as:

  • Destination spa
  • Indoor and outdoor pools
  • Putting green
  • On-site dining
  • Tennis courts

As with most accommodations on this list, the amenities offered differ in each room, but guests can score:

  • Balconies
  • Fireplaces
  • Sitting areas
Winvian Farm

The coolest part of a stay here is the variety of accommodations.

 

Each cabin is very different from the others. Besides the helicopter and treehouse cottages, others were designed after Masonic temples, lighthouses, and many more.

 

This 113-acre estate has 18 cottages, each designed by a different architect to serve as an homage to Connecticut and New England. And guests at Winvian Farm will enjoy all the amenities that match a five-star resort, from bicycles to outdoor pools to a world-class restaurant.

Saybrook Inn and Spa

Nestled at the mouth of the Connecticut River, Saybrook Inn and Spa offers all the amenities of a seaside resort.

 

Some of the most unique parts of a romantic getaway here, however, would be the lighthouse suite, which offers a panoramic view of the water. Of the property’s 82 rooms, it’s the only one with unobstructed views of the water.

Delamar Greenwich Harbor

This 82-room boutique luxury hotel perches above Greenwich Harbor, close to both the Greenwich Train station and I-95. Its luxurious, European-style furnishings and first-rate service have earned the Delamar Greenwich Harbor renown as one of the most elegant destinations in the country.

Madison Beach Hotel

The only hotel in Connecticut that’s directly on the beach, the Madison Beach Hotel offers elegant rooms, decadent spa, and a balcony overlooking Long Island Sound.

 

While the rooms enjoy incredible views as well, there’s nothing better than sitting on that balcony, drink in hand, watching the sunset over the water.

Now, what romantic things to do while enjoying your romantic getaway in CT?

Keeping exploring for more guides on planning your romantic getaway to Connecticut.

 

If you’re coming at a specific time, check out the guides to:

 

Or plan individual dates on your romantic weekend getaway, with our guides to:

 

You should also probably read our guide to free things to do in Connecticut, if you feel like you’ve already planned to spend a lot of money on your visit.