Guilford vacation rentals

We found 735 vacation rentals — enter your dates for availability

Discover a selection of 27 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.

Vacation rentals with weekly discounts - Guilford

Showing deals for:May 29 - Jun 5

Image gallery for Coastal Waterfront Retreat- Private Beach & Hot Tub

You will love our Private Sandy Beach steps from the home, so relaxing:)
10 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)

Coastal Waterfront Retreat- Private Beach & Hot Tub

Branford

9% off
Price is $1,477
$10,336 for 7 nights
All fees included
Coastal Waterfront Retreat- Private Beach & Hot Tub

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Find out more about Guilford

Why visit Guilford

  • Scenic Beaches: Enjoy the picturesque beaches in and around Guilford, perfect for relaxation and outdoor activities.
  • Rich History: Explore historic sites and charming neighborhoods that reflect Guilford's heritage and culture.
  • Outdoor Adventures: Engage in various outdoor activities, including hiking and visiting nearby state parks.
  • Vibrant College Atmosphere: Experience the lively vibe of a college town with cultural events and activities.
  • Diverse Accommodations: Choose from a wide range of vacation rentals, from cozy cottages to modern apartments.

Popular types of accommodation in Guilford

If you're exploring vacation rentals in Guilford, you're in for a treat. Our platform offers a variety of popular accommodations, including houses, charming cottages, and modern apartments. Whether you're seeking cozy cottage rentals or spacious home rentals in Guilford, we have a diverse selection to meet your needs. Discover the best rental listings in Guilford, CT, and enjoy a memorable getaway with all the comfort and reassurance you deserve.

  • Houses: The top choice for travelers in Guilford, offering spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Cottages: A charming option for those looking for a cozy and rustic stay, perfect for a romantic getaway or a relaxing retreat.
  • Apartments: A convenient and versatile choice for travelers seeking a home-like atmosphere with easy access to local amenities.
  • Condos: Popular among vacationers for their modern features and shared facilities, providing a blend of comfort and community.
  • Villas: An upscale option for those desiring luxury and style, ideal for a lavish vacation experience.**

Top attractions near Guilford

Guilford, Connecticut, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering a blend of scenic beauty and rich history. Visitors can explore beautiful beaches, historic colleges and universities, and nearby national and state parks. This charming town caters to diverse interests, providing cultural experiences and family-friendly activities that create lasting memories for every traveler.

  • Yale University: A prestigious Ivy League institution located 13 miles from Guilford, Yale offers a rich cultural experience with its stunning architecture, museums, and vibrant campus life. Explore the Yale University Art Gallery and the Peabody Museum of Natural History for a glimpse into art and science.
  • Hammonasset Beach State Park: Situated 6 miles away, this beautiful state park features sandy beaches, scenic views, and plenty of outdoor activities like swimming, hiking, and picnicking, making it perfect for adventure seekers.
  • Stony Creek - Thimble Islands Historic District: Just 4 miles from Guilford, this charming historic village boasts unique architecture and cultural vibes, along with stunning views of the Thimble Islands, perfect for a leisurely stroll or boat tour.

Things to do recommended for couples

For a romantic getaway in Guilford, savor a delightful meal at Anna Mia's, only 4 miles away. Then, indulge in wine tasting at Chamard Vineyards, 7 miles from town. If you're feeling adventurous, head to Powder Ridge Mountain Park, 15 miles away, for some skiing fun together.

Things to do recommended for families

During your family vacation in Guilford, enjoy exciting sports at Connecticut Sportsplex, relax at the scenic East Rock Park, and create lasting memories on the charming Lighthouse Point Carousel. Each location offers a unique vibe perfect for family fun and togetherness.

Things to do recommended for groups

Groups visiting Guilford can enjoy shopping at Clinton Crossing Premium Outlets and North Madison Shopping Center for a lively retail experience. For a more relaxed vibe, Stony Creek Brewery offers a charming atmosphere perfect for unwinding with friends over craft brews.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Guilford with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Guilford with young kids: Traveling with little ones can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities, like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Guilford: For many families, a vacation isn't truly enjoyable without their furry companions. If you can relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer food bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Guilford: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Guilford

Guilford, Connecticut, offers a delightful mix of outdoor adventures and scenic beauty, making it an ideal destination for romantic getaways and family-friendly vacations. Explore charming neighborhoods that radiate warmth and friendliness, or relax on the picturesque beaches nearby. With a vibrant college town atmosphere and a variety of fun places to visit, Guilford promises a memorable travel experience filled with both relaxation and excitement.

  • New Haven: Located 13 miles away from Guilford, New Haven is a vibrant city steeped in culture and history. Home to the prestigious Yale University, this city offers a rich educational experience alongside diverse shopping areas and a lively music scene. Visitors can explore historic landmarks, enjoy events at conference venues, and relax at nearby beaches. With its unique blend of urban life and cultural attractions, New Haven is perfect for travelers looking for an enriching city-themed experience.
  • Madison: Situated 5 miles from Guilford, Madison is a charming town known for its stunning outdoor scenery and adventurous spirit. With beautiful recreational areas and a welcoming community, it’s an ideal spot for families and nature enthusiasts alike. The town features picturesque beaches and a national state park, perfect for hiking, picnicking, or simply enjoying the fresh air. Madison also hosts engaging music concerts and offers a popular golf course, making it a great destination for outdoor activities.
  • Westbrook: Just 12 miles from Guilford, Westbrook is a delightful destination that combines romance with breathtaking natural beauty. This coastal town offers a variety of attractions, including charming resorts and recreational areas that invite relaxation and adventure. Visitors can unwind at family-friendly beaches or partake in local music concerts. Westbrook is also home to event conference venues, making it a versatile spot for both leisure and gatherings amidst its scenic surroundings.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 HighModerately High
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 SunnyAverageAverage
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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Furthermore, extending your stay often results in even more savings. To discover the ideal Vrbo property that fits your budget, utilize our helpful filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

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

**Based on Vrbo properties bookings.

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 best area to stay in Guilford, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Guilford, Connecticut, the town's charming downtown area stands out as an excellent choice. This vibrant neighborhood is known for its picturesque streets, historic architecture, and a variety of local shops and eateries that create a friendly setting. Visitors can enjoy the beautiful Guilford Green, a lovely park that often hosts community events and offers a serene spot to relax. Additionally, the nearby Guilford Harbor is superb for those who appreciate waterfront activities and scenic views.

Another appealing area is the shoreline, where you can find access to some lovely beaches and coastal parks. This part of Guilford provides opportunities for outdoor activities, such as hiking and swimming, making it ideal for families and nature enthusiasts. The town features a range of vacation rental properties, from cozy cottages to spacious homes, accommodating different group sizes and preferences.
How much does it cost to rent a vacation home in Guilford?
Prices for vacation rentals in Guilford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Guilford to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Guilford vacation house rentals?
You can find great discounts on house rentals in Guilford on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Guilford?
For renting a beach house in Guilford, consider the picturesque shoreline along the Long Island Sound. The area near Jacobs Beach is particularly appealing, known for its sandy shores and family-friendly atmosphere. Vacation rentals here often feature amenities such as private decks with ocean views, outdoor grills for summer barbecues, and easy access to the beach, making it a great choice for families or groups looking to enjoy a relaxing seaside getaway.

Additionally, the neighborhood around the Guilford Town Green offers a charming mix of historic homes and modern rentals, providing convenient access to local shops, cafes, and seasonal events. Many properties in this area come equipped with cozy living spaces, full kitchens, and inviting outdoor areas for enjoying the coastal breeze.

For those who appreciate nature, rentals near the nearby Hammonasset Beach State Park provide access to one of Connecticut's largest beaches, along with hiking trails and picnic areas. Some properties might even include bicycles for exploring the scenic surroundings and convenient access to the park's amenities.
What is the most popular type of vacation rental accomodation in Guilford?
In Guilford, vacation houses are the most popular type of rental, with about 22 available throughout the charming coastal town. These houses often boast spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Many properties feature outdoor spaces such as decks or gardens, superb for enjoying the scenic surroundings and fresh air. Additionally, there are several cottages and cabins that provide a cozy, rustic experience, often located in more secluded areas. Apartments are also available, offering a more compact living option while still providing essential amenities.
Are there any family house rentals in Guilford?
In Guilford, Connecticut, there are numerous family-friendly house rentals available, with around 21 options to choose from. The town's charming neighborhoods offer a variety of spacious homes suited for families, often featuring amenities like full kitchens, large living areas, and outdoor spaces great for children to play. Many properties come equipped with conveniences such as Wi-Fi and air conditioning, ensuring a comfortable stay for all.

Situated along the picturesque shoreline, visitors can easily explore nearby attractions, including the scenic Guilford Green and the historic Guilford Harbor. Families can enjoy local parks, beaches, and walking trails, making this area an ideal destination for those seeking both relaxation and outdoor activities.
Can I rent a vacation home with a pool or hot tub in Guilford?
In Guilford, Connecticut, there are several vacation homes available for rent that come equipped with pools and hot tubs. This charming coastal town offers a mix of serene landscapes and historical charm, making it an inviting destination for travelers seeking relaxation. Many of the available rentals feature private pools, spacious backyards, and outdoor seating areas, superb for enjoying the beautiful New England summers. Additionally, amenities such as fully equipped kitchens, air conditioning, and Wi-Fi are commonly found, ensuring a comfortable stay.
Can I find long-stay vacation rentals in Guilford?
A long-stay vacation rental in Guilford is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Guilford?
In Guilford, travelers can find several pet-friendly house rentals that cater to families and groups looking to enjoy the charm of this coastal Connecticut town. Many of these vacation homes come equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces where pets can roam freely.

The area is known for its beautiful shoreline, and the nearby Guilford Town Green offers a lovely setting for walks. Additionally, the picturesque beaches, like Jacobs Beach, provide ample opportunities for outdoor activities, making it a great spot for pet owners looking to enjoy the sun and surf.

Local parks, such as the nearby Bittner Park, also welcome pets and feature walking trails and open spaces.
Are there any remote work vacation rentals in Guilford?
In Guilford, Connecticut, there are numerous options for remote work vacation rentals, with about 27 available in the area. Many of these properties are equipped with essential amenities for a productive work environment, including high-speed Wi-Fi and dedicated workspace options like desks and comfortable chairs. Travelers can expect a mix of charming homes and cozy apartments, often featuring inviting living spaces, fully equipped kitchens, and outdoor areas for relaxation during breaks.

The town itself is known for its picturesque shoreline and historic sites, providing a peaceful backdrop for those balancing work and leisure. Nearby points of interest include the Guilford Green and the scenic beaches along the Long Island Sound, offering opportunities for outdoor activities and local dining. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Guilford vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Guilford with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Guilford?
In Guilford, popular rental amenities include kitchens, which allow travelers to prepare their own meals, enhancing the home-like experience. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, some properties come equipped with blenders, superb for those who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit Guilford for a vacation rental?
The best time to visit Guilford for a vacation rental is during the peak summer months of June to August, with July being especially popular. This vibrant period attracts families and outdoor enthusiasts eager to explore the charming coastal town. Visitors can enjoy pleasant weather, typically ranging from the mid-70s to low 80s Fahrenheit, superb for beach outings, hiking, and local festivals.

During these summer months, Guilford comes alive with various activities, including the picturesque beaches along the Long Island Sound and the beautiful Guilford Green, where you'll often find art fairs and farmers' markets. The warm temperatures and lively option create an inviting backdrop for outdoor dining and sightseeing.

For those looking for a more budget-friendly experience, consider planning your trip in December. While this month falls outside the high tourist season, it offers a unique charm with holiday decorations and a cozy, festive atmosphere. You may find excellent deals on vacation rentals, allowing you to enjoy the tranquility of Guilford during the quieter winter months.
How early should I book a Guilford vacation rental?
Book your Guilford vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Guilford, Connecticut, United States of America?
In Guilford, visitors can enjoy a variety of attractions that showcase the town's rich history and natural beauty. The historic Guilford Green is a focal point, surrounded by charming historic architecture, shops, and eateries. Here, you can find the First Congregational Church, an iconic landmark with impressive architecture that reflects the town's heritage.

For those interested in the outdoors, Hammonasset Beach State Park offers beautiful sandy shores and scenic walking trails, making it a popular destination for beachgoers and nature lovers alike. The nearby Guilford Lakes is great for kayaking, fishing, and hiking, providing a serene escape into nature.

In addition, the Henry Whitfield State Museum, located in the oldest house in Connecticut, presents fascinating exhibits on the area's historic history, attracting history buffs and families.
Can I change or cancel my Guilford home rental booking on Vrbo?
To find Guilford vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Guilford vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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