Photo by Bibek Magar

Guilford holiday lettings

We found 716 holiday rentals — enter your dates for availability

Discover a selection of 30 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.

Holiday rentals with weekly discounts - Guilford

Showing deals for:10 Oct - 17 Oct

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.

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.

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

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.

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:

  • Chamard Vineyards (6.8 mi / 10.9 km)
  • Chatfield Hollow State Park (6.9 mi / 11.1 km)
  • 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)
  • Putter's Paradise Mini Golf (22 mi / 35.4 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:

  • Chatfield Hollow State Park (6.9 mi / 11.1 km)
  • Hammonasset Beach (7.2 mi / 11.6 km)
  • Clinton Town Beach (8.2 mi / 13.1 km)
  • Double Beach (8.4 mi / 13.6 km)
  • East Haven Town Beach (10.5 mi / 16.9 km)
  • West Silver Sands Beach (11.3 mi / 18.2 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 most popular type of holiday rental accommodation in Guilford?
Houses are the most popular style of holiday rental in Guilford, according to our data. Even if you've got something a little different in mind, Vrbo has holiday homes in many shapes and sizes. Take a look at our options to find your perfect fit.
How much does it cost to rent a holiday rental in Guilford?
Season, length of stay and property type are some factors that can determine the price of a holiday home. Simply click on your travel dates to find your ideal escape. From quaint country cottages to expansive villas, all Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Guilford?
Prices for beach houses in Guilford may differ depending on the size and type of the property and time of year you're travelling. All you have to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow down your search by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday rentals in Guilford?
Pack a travel bag for the pup in your life because Guilford has 30 stays that throw out the welcome mat to pets. Let your four-legged friend enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Guilford?
Grab your swimwear and pool noodle, because there are four houses with a private pool in Guilford. Settle in at one of these sought-after holiday rentals and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Guilford?
When it comes to rental amenities that guests are on the lookout for in Guilford, a barbecue grill, a firepit and an ocean view rank highest. With Vrbo holiday homes, there are choices to suit your style and taste, whether you're going on a holiday with family, friends or even pets.
Are there large group holiday rentals in Guilford?
Guilford has two holiday homes that can host 10 or more guests. These stays come with the space and privacy you need to enjoy good times with your nearest and dearest.
Are there holiday rentals in Guilford that welcome kids?
Guilford has 30 family-friendly holiday rentals to pick from. And tracking down a stay that welcomes kids is simple with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll have access to amenities and perks such as multiple bedrooms, kitchens and yards.
What are the top attractions for families in Guilford?
Keeping the kids entertained during your holiday in Guilford is easy with these exciting family-friendly attractions:

  • Hammonasset Beach
  • Double Beach
  • Stony Creek Museum

Are there one-bedroom holiday rentals in Guilford?
There are three one-bedroom properties in Guilford to pick from. A one-bedroom holiday home is a wonderful choice if it's only two of you or if you're travelling solo. Add in more space, convenience and privacy compared to a regular hotel, and you've got yourself a getaway to remember.
Can I find two-bedroom holiday rentals in Guilford?
Guilford has 10 two-bedroom holiday properties for you to select from. Discover a holiday home with all the space and comfort you're looking for at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in Guilford?
Pick from 15 holiday rentals with WiFi in Guilford. If you'd like to disconnect from daily life during your break, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Guilford?
Select your dates and then use the filter tool to see holiday rentals with air conditioning in Guilford on Vrbo. With 28 air-conditioned properties available, you can enjoy a cool and comfy stay.
How old do you have to be to rent a holiday rental in Guilford?
The minimum age requirements can differ between properties on Vrbo, so be sure to check the rules of the holiday home in Guilford you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday rental in Guilford for?
How long you can rent a holiday rental in Guilford is up to the property. Just enter your desired travel dates to view a list of options offering extended stays. With plenty of features such as air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you're sure to discover the perfect place to call your home away from home in Guilford.

More Holiday Rentals ideas

People also search for