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Guilford vacation rentals

We found 716 vacation rentals — enter your dates for availability

Discover a selection of 30 homes and other vacation rentals in Guilford that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the amenities you need and want, which might include WiFi and a fireplace. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.
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Find out more about Guilford

Find out more about Guilford

Why visit Guilford

  1. Outdoor Adventures: Enjoy beautiful beaches and scenic state parks, perfect for hiking, picnicking, and relaxation.
  2. Family-Friendly Activities: Engage in local adventure experiences and Segway tours that cater to all ages.
  3. Historic Charm: Explore charming historic sites and picturesque beach cottages that reflect Guilford's rich heritage.
  4. Welcoming Atmosphere: Experience the warm hospitality of friendly locals and a tight-knit community vibe.
  5. Diverse Accommodations: Choose from a variety of lodging options, including cozy cottages and convenient guest suites.

Popular types of accommodation in Guilford

Discover the charm of Guilford with a variety of vacation rentals to suit your needs. From cozy apartments and houses to quaint cottages, there's something for everyone. Whether you're looking for a Guilford guest suite for a short getaway or planning an extended stay, you'll find comfortable options, including Guilford motels and suites. Explore your perfect home base for your adventures in this beautiful coastal town!

  • Apartments: The top choice for travelers in Guilford, offering convenient living spaces ideal for individuals or families.
  • Houses: A favored option for those seeking comfort and privacy, perfect for group getaways.
  • Cottages: Charming and cozy, these rentals provide a quaint escape close to nature.
  • Condos: Modern and well-appointed, condos offer a blend of luxury and convenience.
  • House Boats: Unique lodging on the water, perfect for an adventurous stay in Guilford.**

Top attractions in Guilford

Guilford, Connecticut, is an ideal destination for outdoor enthusiasts and families alike, featuring beautiful beaches, scenic state parks, and historic college campuses. Visitors can enjoy a variety of attractions that cater to both culture and adventure, including Segway tours and local adventure experiences. Whether you're exploring the picturesque scenery or engaging in family-friendly activities, Guilford promises a memorable vacation for all travelers.

  1. Yale University: A prestigious institution with stunning architecture and rich history, Yale offers visitors a chance to explore its beautiful campus, museums, and galleries that showcase art and culture.
  2. Hammonasset Beach State Park: This expansive park features sandy beaches, scenic trails, and opportunities for outdoor adventures like swimming, hiking, and birdwatching, making it a perfect spot for nature enthusiasts.
  3. Stony Creek - Thimble Islands Historic District: A charming historic village known for its picturesque waterfront, unique architecture, and cultural heritage, ideal for leisurely strolls and local dining experiences.

Things to do recommended for couples

Ready for a romantic getaway in Guilford? Start your day with wine tasting at Chamard Vineyards, then enjoy a delightful meal at Anna Mia's. For adventurous couples, head to Powder Ridge Mountain Park for some skiing. Embrace the charm and create lasting memories together!

Things to do recommended for families

In Guilford, families can explore the energetic Connecticut Sportsplex, enjoy wellness at East Rock Park, or experience the charm of the Lighthouse Point Carousel. Each location offers unique outdoor fun and relaxation, making for a memorable family vacation.

Things to do recommended for groups

Group travelers in Guilford can enjoy shopping at Clinton Crossing Premium Outlets, relax with craft brews at Stony Creek Brewery, and catch a show at the Toyota Oakdale Theatre, all offering vibrant atmospheres and diverse entertainment options within a short drive from the town.

What do I need to keep in mind when booking a vacation in Guilford

If you're traveling with friends, family, pets, or planning an extended stay, be sure to use the appropriate filters to prioritize your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Guilford with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Guilford with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Guilford: For many families, a vacation wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Guilford: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Guilford

Guilford, Connecticut, offers a delightful blend of outdoor adventures and scenic beauty, making it perfect for family vacations. Visitors can explore charming historic sites, enjoy picturesque beach cottages, and experience the warm atmosphere created by friendly locals. Whether you're seeking a budget-friendly getaway or a relaxing retreat, Guilford's stunning landscapes and family-friendly vibes ensure an amazing travel experience. Don't miss the chance to discover the beauty of this captivating coastal town!

  • New Haven: Located 13 miles from Guilford, New Haven is a vibrant city renowned for its rich cultural scene and academic prestige. Home to Yale University, visitors can explore stunning historic architecture and numerous museums, including the Yale University Art Gallery. The city offers a lively atmosphere with plenty of shopping and dining options, as well as entertainment venues for concerts and events. Don't miss the picturesque beaches nearby, perfect for a relaxing day by the water.
  • Branford: Just 7 miles from Guilford, Branford is a charming coastal town that emphasizes outdoor family activities and scenic landscapes. With its beautiful beaches and tranquil lakes, Branford is ideal for those looking to enjoy nature. Families can partake in recreational activities such as kayaking or picnicking at local parks. The town also features educational opportunities and a friendly community vibe, making it a welcoming destination for tourists.
  • Madison: Only 5 miles from Guilford, Madison is an outdoor lover's paradise, offering stunning scenery and adventure for visitors. With its pristine beaches and access to a national state park, Madison invites exploration of nature trails and outdoor sports. The town hosts various recreational areas perfect for family outings, and music concerts add to its vibrant community spirit. Whether you’re hiking, relaxing on the beach, or enjoying a local event, Madison provides a delightful escape.

Best time to go to Guilford

If you're planning a trip to Guilford, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageModerately Low
April48.4°F (9.1°C)Light RainMostly SunnySlightly HighAverage
May58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnySlightly HighAverage
July74.1°F (23.4°C)Light RainMostly SunnySlightly HighModerately High
August73.2°F (22.9°C)Light RainMostly SunnyAverageModerately High
September66.7°F (19.3°C)Light RainMostly SunnyAverageModerately High
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnySlightly LowAverage
December37.6°F (3.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming travel plans? Staying flexible with your travel dates can help, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner truly has its rewards! By enrolling in our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can now find the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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.

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.

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 (11.2 mi / 18.1 km)
  • Lighthouse Point Park (12 mi / 19.4 km)
  • East Rock Park (12.1 mi / 19.5 km)

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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Guilford?
Cottages are the most popular style of vacation rental in Guilford, according to our data. Even if you’ve got a different vision in mind, Vrbo has vacation homes in all shapes and sizes. Filter our options to find your perfect Guilford pad.
How much does it cost to rent a vacation rental in Guilford?
The average price for a vacation rental in Guilford depends on a number of factors, like property type, length of stay and season. Whether you’d like a sprawling villa with space for extended family or a quaint cottage for just you and your sweetheart, just add your dates of travel to find stays with fantastic value.
How much does it cost to rent a beach house in Guilford?
The average price for a vacation rental close to the beach in Guilford will depend on when you’re going and the size and style of property you’re looking for. You can easily find prices on Vrbo by entering your dates of travel. Then use the handy filters to choose the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in Guilford?
With 34 vacation rentals that allow pets, your furry companion can join you on your Guilford break. Use our filter tool to browse our pet-friendly vacation rentals and find a vacation home that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Guilford?
Tick the “pool” box in our handy filter tool and take your pick of six houses with private pools in Guilford on Vrbo. Gentle soak, ball games or noodle joust? Leisure activities are up to you when your vacation home boasts a swimming pool.
What are popular rental amenities in Guilford?
When it comes to rental amenities that guests prefer in Guilford, a sauna, a swimming pool and a beach view rank the highest. With Vrbo vacation rentals, there are options to suit your style and taste, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in Guilford?
Yes, you’ll find 18 vacation rentals in Guilford that can accommodate a group of five or more guests. From family get-togethers to special occasions like birthday parties, these stays have enough room to chill out with the people that matter the most.
Are there vacation rentals in Guilford that welcome kids?
Guilford has 33 family-friendly vacation homes to choose from. And securing a stay that welcomes kiddos is easy with our “Properties good for families” filter. In addition to having the whole place to yourselves, you can also look forward to perks and amenities such as extra bedrooms, private pools and yards.
What are the top attractions for families in Guilford?
Keeping the kids amused during your vacation in Guilford is a snap with these fabulous family-friendly attractions:

  • Hyland House Museum
  • Henry Whitfield State Museum
  • Bishops Orchard and Winery

Are there one-bedroom vacation rentals in Guilford?
There are four one-bedroom properties in Guilford to choose from. A one-bedroom vacation rental is a wonderful option if it’s only the two of you or if you’re vacationing alone. Throw in more convenience, space and privacy compared to a regular hotel, and you’ve got yourself a trip to remember.
Can I find two-bedroom vacation rentals in Guilford?
Take off with your loved ones and experience complete comfort and privacy in one of the 12 two-bedroom vacation homes Guilford has to offer.
Are there vacation rentals with WiFi in Guilford?
Guilford has 20 vacation rentals with WiFi, so you’ll be able to stay connected while you’re on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Guilford?
There are 28 Vrbo vacation homes with air conditioning in Guilford giving you that cool, cool breeze and extra element of comfort. Just enter your preferred dates of travel and then make use of our filter tool to search for properties with air conditioning.
How old do you have to be to rent a vacation rental in Guilford?
The minimum required age is normally 16, 18 or 21. It can differ across properties on Vrbo, so check the rules of your preferred Guilford vacation home before booking your stay.
How long can I rent a vacation rental in Guilford for?
The length of time you can rent a vacation rental in Guilford is down to the property. Simply enter your desired travel dates to view a list of options offering extended stays. With tons of amenities like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you’re sure to find the perfect place to call your home away from home in Guilford.
Does Vrbo offer discounts for vacation homes in Guilford?
In Guilford, you’ll find some incredible discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re wanting a weekend escape or a few weeks away, we offer a variety of options that’ll suit your style.

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