A romantic weekend away is a good idea in any season, but there’s just something extra-special about getting away together during the colder months. Whether you’re looking to battle the early-darkness blues or escape the mayhem of the festive season, Kent is the perfect destination for a cosy season staycation.
Easily accessible from London within just a couple of hours, the Garden of England provides perfect respite from the fast pace of the city, with quaint coastal towns and charming chocolate-box villages. Below, we’re listing some of the very best things to do for couples in Kent. Whether you’re visiting for a weekend or a short break, consider this your go-to guide for a romantic weekend with your favourite person.

Step 1: Book a cosy cottage for two
Kent is teeming with indulgent and inspiring places to stay – from freshly shucked oysters in Whitstable on the north coast, to elegant Georgian architecture and antiques in Deal. Historic country homes and traditional fishermen’s cottages make up most of the accommodation in this age-old corner of Britain, meaning you’ll be seriously spoilt for choice. Equipped with contemporary comforts and little luxuries, our collection of romantic cottages in Kent includes seafront serenity at Seaside Cottage, countryside calm at Moat Farm Cottage and amazing interiors at Witenstaple.
If you want fabulous walks from the doorstep combined with a wealth of options for food, drink and things to do, consider a getaway to Kingsdown, Whitstable or Deal.

Step 2: Take a scenic walk along the coast or through the countryside
Renowned for great walks with pub-lunch pit stops and calming coastal panoramas, Kent is a great option for those who enjoy spending time outdoors. We’ve rounded up some of our (top secret) favourite walks in Kent here, along with some unmissable autumnal strolls which are great in any season. Besides the rolling hills and storybook woodlands, there are also countless beaches where you can get your fix of fresh air and sea views – some of our favourites include the stretch of shingle between Deal and Walmer, or the sandy Botany Bay with its chalky sea stacks.

Step 3: Wine, dine and be wooed at some of Kent’s best restaurants
The diverse terrain of Kent, with its mostly dry and warm climate, produces some seriously great food and drink. Besides delicious wine varieties that often draw comparisons to France’s chalky Champagne terroir, the county is also known for its seafood and other local produce. The emerging foodie scene here has captured the attention of everyone from The Good Food Guide to the more elusive individuals behind the Michelin Guide.
Whether your idea of a romantic meal out looks like fresh fish and chips on the beach or a tasting menu in a swanky new spot, Kent has got you covered. The Keepers team’s favourites for romantic restaurants in Kent include:
- Sargasso, Margate
- Updown Farmhouse, near Deal
- Boys Hall, Ashford
- Kebbells, Broadstairs
- Hide and Fox, Hythe
- Bottega Caruso, Margate
- The Rose, Deal
- Seabird, Ramsgate
- The Fordwich Arms, near Canterbury
Want to score extra brownie points by serving a delicious breakfast in bed? STAPLE is an artisanal bakery and cafe with a few locations throughout Kent.

Step 4: Step into the pages of a romance novel at a castle
Widely recognised as the oldest county in England, Kent has its fair share of truly enchanting castles and Austenian country manors. These historic sites make for a relaxing and romantic morning or afternoon out, so we’ve listed a few known for their impressive grandeur and glorious grounds.
Leeds Castle – Just 7 miles from Maidstone, Leeds Castle dates back to 857 and was once used by Henry VIII as a residence for his wife, Catherine of Aragon. Encircled by an impressive moat, the present structure dates mostly from the early 19th century and is a must-see.
Scotney Castle – The epitome of storybook romance, Scotney Castle is home to a heavenly trifecta – dotted with pockets of ancient woodland, you’ll find a handsome Victorian mansion, the ruins of a medieval castle and acres of rolling parkland. A true feast for the senses, you could also visit the nearby Bedgebury National Pinetum & Forest.
Dover Castle – Described as ‘the Key to England,’ Dover Castle cuts a striking shape atop a chalk bluff overlooking the town below. Offering a fascinating insight into its 11th-century origins, the grounds and interiors of the fortress also boast stunning sea views.
Other stunning settings to explore together include Hever Castle, Penshurst Place, Knole, Quebec House and even Chartwell, the beloved home of Sir Winston Churchill.
Plan a romantic retreat in Kent with Keepers Cottages
Sold on a cosy staycation? Allow us to sweep you off your feet with our collection of over 150 charming Kentish cottages. Each individually vetted and approved by us, our properties occupy a range of different locations throughout Kent. Enjoy a weekend at the coast or deep within the countryside – find your perfect cottage here.
Need a little help or advice to plan the perfect romantic break? We’d be happy to help! Call us on 01304 382044 or send an enquiry to enquiries@keeperscottages.co.uk.