Discover a selection of 500 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 $235 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.

Natural features

Exploring the natural features in Guilford

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Guilford. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Hammonasset Beach State Park (6.2 mi / 10 km)
  • Hammonasset Beach (7.2 mi / 11.6 km)
  • East Haven Town Beach (10.5 mi / 16.9 km)
  • Westbrook Town Beach (11.3 mi / 18.3 km)
  • Lighthouse Point Park (12 mi / 19.4 km)
  • New Haven Green (13.1 mi / 21.2 km)
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.

What are the top vacation rentals in or near Guilford?

Whether you're searching for an intimate retreat for you and your sweetie or a sprawling house to fit all your friends, you'll find some top vacation rentals in and around Guilford. Here are a couple to start you off:

  • Make use of handy amenities like free WiFi and a hair dryer at "Beach Cottage Close To Silver Sands State Park". Located around 20 miles from Guilford, this unique option has 2 bedrooms and is a hit with guests.
  • Another excellent choice is "Stunning Private Guilford Estate. Located At The End Of A Sublime Cul", which is around 2 miles from Guilford. With 4 bedrooms, a garage and a dryer, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Guilford vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Guilford?

Escape from the hustle and bustle of everyday life at one of our weekend getaways in or near Guilford. Whether you'd like to catch up with pals or spend treasured time with the kids, we'll have something to suit your style. These top-rated options are hard to beat:

  • "Birdsong - Relaxation, Activities And Culture In Quaint Shoreline Town" is ideal for a weekend of relaxation and fun. It offers a range of amenities, such as nearby museums and coffee and tea making facilities, and is located roughly 2 miles to the northeast of Guilford.
  • Alternatively, create new memories with your loved ones at "Enjoy A Taste Of New England In Historic Guilford Ct", which is around 3 miles to the south of Guilford. Take advantage of towels, heating and more here.

Can I find studio apartments for rent in and around Guilford?

Studio apartments are a simple yet stylish option, ideally suited for one or two guests. Spend your days exploring your surroundings and your nights relaxing in your comfy hideaway. These getaways in or near Guilford are guaranteed to please:

  • After a fun-filled day of outdoor exploration, relax in total comfort at "Birdsong - Relaxation, Activities And Culture In Quaint Shoreline Town". A smart TV and a restaurant dining guide are among the handy amenities on offer here.
  • Alternatively, use "Your Own Thimble Islands Private Bungalow - Accessible By Car Via Old Quarry" as a base to tick off the best attractions around you. This cozy home away from home comes with a stovetop, towels and more.

Can I find short term rentals in or near Guilford?

Whether you're looking for a cottage for two or a house with space for the whole family, short-term rentals are easy to find in and around Guilford. These properties make the perfect base for a quick visit:

  • If you can only spare a few nights, "Spacious Water View House Nxt To Sandy Beach" is a good choice. It's close to the center of Guilford, so you'll be near all the top sights.
  • Alternatively, book a couple of nights at "Private Luxury Waterfront Home". This comfy, conveniently located property makes it easy to explore the area's sights.

What are the best romantic weekend getaways in or near Guilford?

Whether spent in a cottage, a cabin or a condo, a romantic weekend getaway is a perfect way to spice up your relationship. Whisk your sweetheart off for a couple of relaxing days at one of these popular escapes in or near Guilford:

  • Located around 20 miles from Guilford, "Beach Cottage Close To Silver Sands State Park" is the ideal place for doting lovebirds. A nearby bay and air conditioning are some of the amenities you'll find here.
  • Another place where you can enjoy a few dreamy days together is "Stunning Private Guilford Estate. Located At The End Of A Sublime Cul". Located 2 miles from Guilford, winery tours and a sauna add to the ambiance here.

What are the best large group vacation rentals in or near Guilford?

Share your vacation and boost your odds of having fun. Whether you're organizing an adventurous escape with buddies or a family reunion, you'll have your choice of large group vacation rentals in and near Guilford:

  • A nice range of amenities including a fireplace and a garden make "The Queen Of The Thimble Islands" a group favorite. This sprawling getaway has 8 bedrooms and accommodates up to 15 guests. From the heart of Guilford, it's around 6 miles away to the southwest.
  • Invite as many as 12 of your friends to "Private Island Victorian Estate In The Thimbles" and fill the place with love and laughter. This option has 4 bedrooms and is around 6 miles to the southwest of Guilford. It's packed with features to keep your group happy and comfortable, including an ocean view and a chef.

What are the best houses for rent with a pool in or near Guilford?

Of all the conveniences a vacation rental can have, a pool is hands down the most fun. Browse these houses for rent with a pool in or near Guilford and spend your time splashing around. Just don't forget to bring your inflatable swan:

  • Make yourself comfortable at "Spacious Water View House Nxt To Sandy Beach", where your highest priority will be chilling by the pool. Amenities such as childrens activities and nearby birdwatching activities help make this escape a favorite with guests.
  • Otherwise, spend your break at "Private Beachfront House In Madison Ct". In addition to its inviting pool, make use of coffee and tea making facilities and beach sun loungers.

Guilford has a humid subtropical climate, with average summertime temperatures ranging from 65 ºF to 80 ºF. But there's no need to wait until summer to visit. Take a look at the search bar at the top of the page and adjust the filters to find the perfect Guilford vacation rental and organize your getaway for whenever you like.

What are the best large family vacation rentals in or near Guilford?

Every family get-together should be a memorable one. Whether you're planning a fun escape with the kids or a reunion with the extended family, Vrbo's large family vacation rentals in or near Guilford offer a comfy home away from home with enough space for everyone:

  • Sleeping up to 8 guests in 4 bedrooms, "Stunning Private Guilford Estate. Located At The End Of A Sublime Cul" is the ideal place to spend time together. This top-rated retreat is 2 miles to the southwest of Guilford and has amenities such as a smart TV and childrens activities.
  • Another popular choice is "Spacious Water View House Nxt To Sandy Beach". This vacation rental is 4 miles south of Guilford and features nearby birdwatching activities, childrens activities and more. With 4 bedrooms accommodating up to 8 people, you won't have to leave anyone off your guest list.

If you'd like to sightsee, there are loads of family-friendly attractions close by to put on your wish list. Lighthouse Point Carousel, Connecticut Children's Museum and Shepaug Eagle Observation Area are good places to start.

Are there one-bedroom vacation rentals in or near Guilford?

Romantic getaways, work trips or adventures of the solo kind — a single-bedroom vacation rental works for a multitude of occasions. One of these options in or near Guilford is sure to fit the bill:

  • It's true! Great things come in small packages, and "Birdsong - Relaxation, Activities And Culture In Quaint Shoreline Town" is a fantastic example of this. This one-bedroom vacation property can be found just a short distance from the center and includes amenities like a garden and a kitchen.
  • "Charming Lakefront Cottage" is another comfortable one-bedroom escape also a stone's throw from the center. When you're not out discovering the area's top attractions, enjoy a garden and a kitchen.

Are there vacation rentals with fire pits in or near Guilford?

Whether you want to share a bottle of red beside the flames with your love or just stay warm once the sun sets, Vrbo will help you find a vacation rental with a fire pit. Check out these top options in or near Guilford:

  • "Sundrenched 5 Bedroom Home With Private Dock Near Beaches" offers a nearby waterfront, a nearby river, and of course, a fire pit. Break out the guitar and have a singalong, share scary stories or just kick back with the fam at this top retreat.
  • Alternatively, let the flickering flames lull you into a state of relaxation at "Madison, Ct - Coastal Modern Farmhouse W". When you're not socializing around the fire pit, make use of conveniences like a fireplace and a kitchen.