Guilford, CT, USA

Guilford, CT, USA

We found 172 vacation rentals — enter your dates for availability


Find the best place to stay — Guilford

Where to stay near Guilford, CT?

Our 2018 property listings offer a large selection of 172 vacation rentals near Guilford. From 105 houses to 45 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Guilford for a holiday or a weekend are on HomeAway.

A scenic slice of New England

Set on the Long Island Sound shoreline, Guilford is a laid-back summer town just 20 minutes from Yale University. This makes Guilford vacation rentals eternally popular with parents, students and professors alike. The town is a haven for sun seekers, with a handful of sandy beaches to enjoy, not to mention forested walking trails, scenic paddling routes and a friendly local golf course. History buffs will be in their element, as Guilford boasts one of New England's largest collection of historic homes.

Hit the sand or the green

One of Guilford's biggest drawcards is its pristine coastline. It's laced with sandy beaches and low-slung dunes that lure a constant stream of sun seekers. Want to maximize your time at the beach? Guilford vacation rentals put you just steps from the water. With breezy living areas, sun decks and sweeping views of Long Island Sound, summer cottages make it easy to slip into vacation mode. If you want to stretch your legs, why not enjoy a round at Guilford Lakes Golf Course? Non-members are welcome so don't be shy about booking a tee time.

Touch base with van Gogh

Whether you're attending a graduation ceremony or simply visiting an Ivy League college, Guilford is a short drive from Yale University. The 300-year-old New Haven campus is dotted with Gothic and Victorian-inspired buildings. You can sign up for a guided walking tour or visit world-class galleries like the Yale Center for British Art. If van Gogh is on your wish list, don't miss Yale University Art Gallery, where you'll find masterpieces like "The Night Cafe". Closer to home is the characterful Hyland House Museum. It's housed in a red saltbox building and showcases a fascinating collection of local artifacts.

Gear up for graduation season

Visitors flock to Guilford in the summer, when the town is drenched in East Coast sunshine. Long weekends always fill up fast with New Yorkers wanting to escape the city. Visitor numbers also soar during Yale's annual University Commencement in May. It's held at the historic Old Campus and sees university degrees formally conferred. Followed by a sea of flying graduation hats, of course. Planning on watching a loved one graduate? Swap shoebox hotel rooms for spacious Guilford vacation rentals. All you need to do is supply the bubbly.

Escape the Big Apple

While it's just 100 miles from New York City, Guilford feels worlds away from the buzz of the Big Apple. Protected by Long Island Sound, Jacob Beach treats visitors to calm water and plenty of picnic spots. Nearby Chaffinch Island Park is another local favorite, with sweeping views of Long Island Sound. The rugged Thimble Islands sit just offshore and are popular with boat cruises and kayakers. Discovered in 1614, they were once used for farming, quarrying and bootlegging. Today, they're a haven for local wildlife, including seals and great blue herons.