Guilford holiday lettings

We found 742 holiday rentals — enter your dates for availability

Discover a selection of 27 homes and other holiday rentals in Guilford that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Why visit Guilford

  • Picturesque beaches: Enjoy the stunning shoreline and relax by the beautiful waterfront in Guilford.
  • Rich history: Explore historic colleges and charming architecture that reflect the town's cultural heritage.
  • Outdoor activities: Discover state parks and nature trails perfect for hiking and enjoying the great outdoors.
  • Trendy city centre: Stroll through vibrant streets filled with friendly locals, shops, and dining options.
  • Varied accommodation: Choose from delightful holiday rentals, including cosy cottages and stylish apartments.

Popular types of accommodation in Guilford

If you're considering a getaway to Guilford, you'll find a delightful range of holiday rentals to suit your needs. Our most popular options include charming houses, cosy cottages, and stylish apartments. Whether you're looking for house rentals in Guilford or seeking the perfect holiday lettings, we’re here to help you discover the ideal stay for your visit. Experience the charm of Guilford with our exceptional selection of holiday rentals.

  • Houses: A preferred choice for visitors to Guilford, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: These delightful, often quaint accommodations provide a charming and picturesque escape.
  • Flats: A practical option for those seeking convenience, offering a home-like atmosphere in the heart of Guilford.
  • Condos: Modern and well-equipped, condos offer more amenities for a relaxed stay.
  • Villas: Luxurious retreats that provide an upscale experience with ample space and privacy.**

Top attractions near Guilford

Guilford, Connecticut, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore picturesque beaches, historic colleges, and state parks that showcase the region’s natural beauty and cultural heritage. With a variety of attractions available, Guilford offers something for everyone, making it perfect for families and those looking to immerse themselves in the local culture.

  • Yale University: A prestigious institution located 8.1km from Guilford, Yale boasts stunning architecture and rich cultural heritage. Explore its museums and beautiful campus, immersing yourself in academic history.
  • Hammonasset Beach State Park: Situated 3.7km away, this expansive park offers a picturesque coastline and outdoor adventures. Enjoy swimming, hiking, and stunning scenery amidst nature's beauty.
  • Stony Creek - Thimble Islands Historic District: Just 2.5km from Guilford, this charming village features historic homes and breathtaking views of the Thimble Islands, perfect for cultural exploration and seaside relaxation.

Things to do recommended for couples

For a romantic getaway in Guilford, indulge in a delightful meal at Anna Mia's, explore the enchanting Chamard Vineyards, or embrace winter sports at Powder Ridge Mountain Park. Each experience offers a unique charm, perfect for couples seeking memorable moments together.

Things to do recommended for families

Families visiting Guilford can experience the excitement at the Connecticut Sportsplex, the tranquil surroundings of East Rock Park, and the charming Lighthouse Point Carousel, perfect for creating lasting memories together in a delightful outdoor setting.

Things to do recommended for groups

In Guilford, groups can enjoy shopping at the nearby Clinton Crossing Premium Outlets, indulge in literary finds at RJ Julia Booksellers, or unwind with craft beers at Stony Creek Brewery, all offering a delightful mix of local charm and entertainment.

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

If you’re travelling with a group, family, or pets, or if you're considering an extended stay, it's important to prioritise your search accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Guilford with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Guilford with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, considering your closeness to family-friendly attractions can be beneficial.
  • Taking your pets with you to Guilford: For many, a family holiday feels incomplete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all family members feel completely at home.
  • Planning for a long term stay visiting Guilford: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider additional features in your search, such as a parking space, a well-equipped kitchen, or even a private pool.

Where to stay near Guilford

Guilford, Connecticut, offers a delightful blend of outdoor scenery and romantic charm, making it perfect for a relaxing getaway. Explore the trendy areas and the vibrant city centre filled with friendly faces, or unwind by the picturesque waterfront. Nearby, you'll find family-friendly neighbourhoods that cater to all budgets, ensuring a memorable experience. Embrace the mix of luxury and laid-back vibes that Guilford has to offer during your visit.

  • New Haven: Located 8.1km from Guilford, New Haven is a vibrant city renowned for its rich cultural scene. Home to prestigious institutions like Yale University, visitors can immerse themselves in a plethora of educational and historical attractions. The city boasts a lively shopping area, diverse dining options, and a dynamic music concert scene. Highlights include the historic campus, the Shubert Theatre for performances, and nearby beaches that invite relaxation and exploration.
  • Madison: Just 3.1km from Guilford, Madison is a charming coastal town celebrated for its stunning outdoor landscapes and adventure opportunities. Visitors can enjoy the picturesque beaches, including a family-friendly spot perfect for a day of sun and sand. Madison’s recreational areas cater to outdoor enthusiasts, offering sailing, fishing, and golf courses. The nearby Hammonasset Beach State Park is a must-visit for nature lovers, providing scenic trails and beautiful coastal views.
  • Branford: Situated 4.3km from Guilford, Branford is an idyllic town that combines outdoor beauty with romantic settings. This scenic locale features tranquil beaches and inviting lakes, making it ideal for leisurely strolls and picnics. Branford is also known for its recreational areas where visitors can engage in various activities, including skiing in the winter months. The town's charming atmosphere and natural beauty create a perfect backdrop for couples and families alike to enjoy quality time together.

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 simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often lead to substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last stopped, or review and arrange your travel plans. You can easily locate properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The trendy area of Guilford awaits your stay

Enjoy the wineries and other features of Guilford. This trendy and welcoming city entices travellers with its restaurants and sightseeing. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Guilford

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Guilford a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Powder Ridge Mountain Park and Resort (15.1 mi / 24.3 km)
  • Machimoodus State Park (17.6 mi / 28.3 km)
  • Brownstone Exploration & Discovery Park (19.8 mi / 31.9 km)
  • Timberlin Golf Course (22.9 mi / 36.9 km)
  • TPC River Highlands (23.8 mi / 38.3 km)
  • Mount Southington Ski Area (24.1 mi / 38.7 km)

Exploring the natural features in Guilford

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Guilford is a great place to spend some time outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Chaffinch Island State Park (1.6 mi / 2.6 km)
  • Hammonasset Beach (7.2 mi / 11.6 km)
  • Clinton Town Beach (8.2 mi / 13.1 km)
  • East Haven Town Beach (10.5 mi / 16.9 km)
  • West Silver Sands Beach (11.3 mi / 18.2 km)
  • Westbrook Town Beach (11.3 mi / 18.3 km)

Travelling 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 centre. 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're travelling by train, you can make your way to Guilford Station.

Frequently asked questions

What is the best area to stay in Guilford when booking a holiday rental?
When seeking the ideal area to stay in Guilford, Connecticut for a holiday rental, the town centre is a fantastic choice. This charming area offers a delightful blend of historic architecture and modern amenities, making it a lovely place to explore. You'll find a variety of properties available, ranging from quaint cottages to more spacious homes, suiting different tastes and budgets.

Staying in the town centre puts you within walking distance of key attractions, such as the picturesque Guilford Green, a great spot for leisurely strolls and community events. The nearby Guilford Art Centre also adds a cultural touch, offering classes and exhibitions that showcase local talent. Additionally, the area boasts easy access to the scenic coastline, where you can enjoy beautiful beaches and waterfront activities.

Another great option is the neighbourhood surrounding the scenic shoreline, which offers a more tranquil atmosphere. This area features several properties that overlook the water, providing stunning views and a peaceful retreat. Here, you can explore the nearby Hammonasset Beach State Park, known for its expansive sandy beach and nature trails, great for both relaxation and outdoor adventures.
How much does it cost to rent a holiday home in Guilford?
Prices for holiday 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 holiday 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, the scenic shoreline along the Long Island Sound is a prime area to consider. The neighbourhood of Jacobs Beach is particularly appealing, offering direct access to a sandy beach and picturesque views of the water. Many properties in this area come with amenities such as outdoor decks, barbecue facilities, and spacious living areas, superb for families or groups looking to enjoy a coastal retreat.

Additionally, the nearby area around the Guilford Town Green provides a charming atmosphere with easy access to local shops and restaurants. Here, you might find historic homes turned into holiday rentals, often featuring characterful interiors, large gardens, and proximity to both the beach and the quaint downtown area.

For those who enjoy outdoor activities, the nearby Hammonasset Beach State Park offers expansive sandy beaches and picnic areas, making it an excellent spot for day trips. Rentals in this vicinity typically provide amenities like outdoor seating, beach access, and sometimes even bicycles for exploring the surrounding area.
What is the most popular type of holiday rental accomodation in Guilford?
In Guilford, holiday houses are the most popular type of holiday rental, with about 88 available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, large kitchens, and living areas that are great for families or groups. Many also come with outdoor spaces such as gardens or patios, allowing guests to enjoy the scenic surroundings. Additionally, there are around 24 cottages available, which offer a charming, cozy escape with amenities similar to those found in holiday houses. A few cabins and apartments can also be found, providing further variety for travellers looking for a comfortable stay near the picturesque coastline and local attractions.
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. This charming coastal town offers a wonderful blend of natural beauty and historical attractions, making it an ideal destination for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Amenities such as Wi-Fi and air conditioning are commonly found, ensuring a comfortable stay for all ages.

Families can explore nearby points of interest, including the picturesque Guilford Green and the stunning beaches along Long Island Sound. The town is also home to various parks and recreational areas, providing ample opportunities for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Guilford?
In Guilford, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque coastal town offers a charming atmosphere with beautiful scenery and a rich history. Many of the properties come equipped with amenities such as private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens, superb for families or groups looking to enjoy a comfortable stay.

Travellers can also explore the nearby beaches and enjoy local attractions, including parks and nature reserves.
Can I find long-stay holiday rentals in Guilford?
A long-stay holiday rental in Guilford is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Guilford?
In Guilford, there are several pet-friendly house rentals available, providing an inviting space for travellers with pets. Many of these properties come equipped with comfortable amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.

The charming town is known for its picturesque coastal setting, and you'll find holiday rentals that offer easy access to nearby beaches and parks. In particular, the scenic Jacobs Beach is a lovely spot for both humans and pets to enjoy. Additionally, the nearby Guilford Town Green features walking paths and open spaces that are great for leisurely strolls with your furry friends.
Are there any remote work holiday rentals in Guilford?
In Guilford, Connecticut, there are numerous options for remote work holiday rentals, with around 108 available. This picturesque coastal town offers a blend of natural beauty and a quaint New England atmosphere, making it an ideal spot for those looking to work while enjoying a serene environment. Many properties are equipped with reliable Wi-Fi, ensuring connectivity for remote work needs.

Travellers can expect a variety of amenities in these rentals, including comfortable workspaces, fully equipped kitchens for convenient meal preparation, and cosy living areas great for relaxation after a day of work. Some accommodations may also feature outdoor spaces, such as patios or gardens, which can provide a refreshing change of scenery during breaks.

Guilford's charming downtown area is nearby, where visitors can explore local shops and restaurants, as well as the scenic shoreline with its beautiful beaches and parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Guilford holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Guilford with parking available—perfect for families or travellers 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 fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature outdoor spaces such as decks or patios, great for enjoying the pleasant Connecticut weather. Onsite parking is commonly available, making it convenient for those travelling with a vehicle. Additionally, some rentals may provide amenities like blenders, which can be useful for making smoothies or cocktails.
When is the best time to visit Guilford for a holiday rental?
July is the most popular month to visit Guilford, Connecticut, when the summer season is in full swing. This peak season, stretching from June to August, welcomes visitors seeking a blend of coastal charm and outdoor activities. With pleasant temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for exploring the beautiful beaches, scenic parks, and vibrant local festivals.

During July, you can enjoy a lively option, with plenty of opportunities for swimming, hiking, and experiencing the local culture. The warm weather also encourages outdoor dining at charming cafés and restaurants along the picturesque shoreline.

For those looking to travel on a budget, December offers a quieter experience with its own unique charm. Although it's the low season, visitors can enjoy the festive holiday decorations and a peaceful ambiance, making it superb for a cozy retreat.

Ultimately, choosing the right time to visit Guilford depends on your preference for summer vibrancy or a tranquil winter escape.
How early should I book a Guilford holiday rental?
Book your Guilford holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Guilford?
In Guilford, visitors can enjoy a variety of attractions that highlight the town's charming New England character. The historic Guilford Green is a central hub, surrounded by quaint shops, cafes, and the striking First Congregational Church. Nearby, the Guilford Art Centre offers exhibitions and classes, showcasing local talent and crafts.

For nature enthusiasts, the nearby Hammonasset Beach State Park provides beautiful sandy shores and walking trails, great for a day of relaxation or outdoor activities. The Guilford Lakes area features picturesque landscapes, ideal for hiking and enjoying the serene environment.

Additionally, the town boasts several historic sites, including the Henry Whitfield State Museum, which is the oldest house in Connecticut, offering insights into the region's historic history.
Can I change or cancel my Guilford home rental booking on Vrbo?
To find Guilford holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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