Discover a selection of 455 vacation rentals in Guilford, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $200 per night, and houses and cottages are popular options for a stay in Guilford. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Guilford
Destination guide

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.

Things to do

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.


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.


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.

How to get there

Traveling to and around Guilford

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 11.3 mi (18.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 25.3 mi (40.8 km) away.

If you prefer train travel, the main station is Guilford Station.

How many vacation rentals are available around Guilford, CT?

Our 2022 property listings offer a large selection of 455 vacation rentals around Guilford. From 352 house rentals to 85 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Guilford?

Vrbo offers a large selection of vacation rentals near lovely places in Guilford. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Guilford Art Center: 492 vacation rentals
  • Bishops Orchard and Winery: 449 vacation rentals
  • Chaffinch Island State Park: 551 vacation rentals
  • Henry Whitfield State Museum: 510 vacation rentals
  • Guilford Station: 531 vacation rentals

But there are many other points of interest around Guilford listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Guilford?

Yes, of course. Vrbo has 352 Houses in Guilford. Our other popular types of vacation rentals in Guilford include:

  • Cottages: 85 rentals available
  • Condos/Apartments: 93 rentals available
  • Cabins: 85 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Guilford?

Yes, you can select your preferred vacation rental with pool among our 25 vacation rentals with pool available in Guilford. Please use our search bar to access the selection of vacation rentals available.