Discover a selection of 390 vacation rentals in Guilford 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 kitchens. 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.
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.

Natural features

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.

How to get there

Traveling to and around Guilford

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 10.7 mi (17.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 25 mi (40.3 km) away.

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

How many vacation rentals are available around Guilford?

Our 2020 property listings offer a large selection of 390 vacation rentals around Guilford. From 226 house rentals to 93 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a beachfront property in Guilford?

Don't just spend a morning at the beach. Round up your squad and crash as close as you can to it! The sound of waves and awesome ocean views? We'd say it's a no-brainer! Luckily, there are 118 beachside vacation rentals to whisk yourself away to. Alternatively, you might like to try another style of setting. Vrbo has tons of options, including:

  • 98 seaside vacation rentals.
  • 94 water-view vacation rentals.
  • 93 beach-view vacation rentals.

Can I rent a house in Guilford?

If you want an authentic vacation experience and don't feel like sharing space with strangers this time round, renting a whole house is the way to go. There are 229 houses available on Vrbo. Prices start from $32 a night. If that doesn't fit with your group's taste, we've got a range of different property types to pick from, such as:

  • Cottage: 92 vacation homes. Prices start from $95 per night.
  • Apartment: 43 vacation homes. Prices start from $75 per night.
  • Hotel: 25 vacation homes. Prices start from $50 per night.

Can I stay in Guilford in a large group?

Nothing compares to getting together with your old friends or spending a couple of weeks with your beloved relatives in a fantastic new area. What's best, Vrbo has places big enough for the whole squad. House vacation homes are the favorite choice for big groups of guests, with 52 featured here. In this area, the rental properties that can accommodate bigger groups include:

  • If yours is a group of 6, we've got 204 vacation homes perfectly suited for that size. Stay a night from just $67.
  • If you have 8 in your squad, you'll be thrilled to discover that there are 142 vacation homes perfect. The starting price is $170 per night.
  • Looking for properties for rent catering to 10 guests? You'll be pleased to discover we have 86 that will fit the bill. You can book one for as little as $195 a night.

So never fear! When you book with us you can take your dad, your grandma and all your besties to Guilford.

Where are the cheapest rentals in Guilford?

Vrbo is here to help you make memories with your nearest and dearest. Providing a broad selection of value-packed rentals, you're sure to get an incredible hideout that caters to one and all. Essex Village is a great area to take a look at if you want to keep a handle on your budget. Vrbo has 3 rentals, and the average price is a very affordable $193 per night. Old Saybrook Center is another place to consider. Vrbo has 29 rentals here, and the average price is around $271 a night.

Explore destinations around Guilford