Photo by Bibek Magar

Guilford holiday homes

We found 700 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:19 Dec - 26 Dec
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Why visit Guilford

  • Picturesque Beaches: Relax on beautiful beaches and enjoy stunning waterfront views, perfect for a romantic day out.
  • Historic Downtown: Wander through the charming downtown area filled with quaint shops and delightful eateries.
  • Outdoor Activities: Explore nearby state parks and enjoy golfing at the scenic Guilford Lakes Golf Course.
  • Cultural Experiences: Discover local history and enjoy family-friendly events throughout the year.
  • Relaxed Atmosphere: Experience the laid-back vibe of Guilford, ideal for both budget-conscious and luxury travellers.

Top attractions near Guilford

Guilford, Connecticut, offers a delightful mix of outdoor and scenic experiences perfect for a romantic getaway. Explore its beautiful beaches, historic college campuses, and nearby state parks. Enjoy a stroll around the town green, take in the stunning waterfront views, or tee off at the Guilford Lakes Golf Course. Whether you're after cultural experiences or family fun, Guilford has something for everyone to enjoy on your holiday.

  • Yale University: A prestigious institution steeped in history and culture, Yale offers stunning architecture and beautiful campuses. Explore its art galleries and libraries, and soak in the vibrant academic atmosphere just 20.9km from Guilford.
  • Bill Miller’s Castle: A romantic venue set in a charming castle, perfect for a picturesque outing. With its elegant design and cultural events, this delightful spot is only 6.4km away, making it an ideal choice for a memorable experience.
  • Clinton Town Beach: A beautiful beach destination 12.9km from Guilford, Clinton Town Beach boasts soft sand and inviting waters. Enjoy a relaxing day soaking up the sun or taking a dip in the sea, embodying classic beach vibes.

Things to do recommended for couples

Guilford offers delightful couple experiences. Enjoy a romantic meal at Anna Mia's, indulge in fine wines at Rose Vineyards, or hit the slopes together at Powder Ridge Mountain Park. Each spot promises special moments and great vibes for your getaway.

Things to do recommended for families

Families can have a blast at the Connecticut Sportsplex, only 12.9km from Guilford, before enjoying some fresh air and wellness at East Rock Park, 19.3km away. Don’t miss the fun at Lighthouse Point Carousel, also 19.3km out, perfect for outdoor family vibes.

Things to do recommended for groups

While in Guilford, your group can shop at the Clinton Crossing Premium Outlets or the North Madison Shopping Center for a local vibe. For a unique experience, visit Stony Creek Brewery to enjoy some craft brews in a relaxed setting.

*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

If you're heading off on a trip with a group, family, pets, or planning for an extended stay, it's important to set your filters according to your priorities. Here are some handy Vrbo booking tips to help you out.

  • 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 get-togethers. Thankfully, you can refine your search for all of these options and more on Vrbo.
  • Traveling to Guilford with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Guilford: For many, a family holiday isn’t truly finished without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Guilford: If you’re on the hunt for holiday rentals that offer great deals 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 accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Guilford

Guilford, Connecticut, is a charming small town perfect for outdoor adventures and romantic getaways. Explore the picturesque downtown with its quaint shops and eateries, or meander through scenic parks. Nearby, you'll find family-friendly neighborhoods and luxurious spots that offer a relaxed atmosphere. Whether you're after a budget-friendly stay or a touch of luxury, Guilford and its surroundings provide a delightful blend of experiences for every traveller.

  • New Haven: New Haven is a vibrant city located 20.9km away from Guilford, renowned for its rich cultural offerings and educational institutions, including the historic Yale University. Visitors will find a delightful mix of museums, art galleries, and live music venues that cater to all ages. The shopping areas offer a blend of local boutiques and well-known brands, making it a great spot for retail therapy. Don't miss out on the beautiful beaches nearby, perfect for a relaxing day by the water, or the various events held at conference venues throughout the year. New Haven truly embodies a lively city experience with something for everyone.
  • Westbrook: Just 19.3km from Guilford, Westbrook is the ideal destination for those seeking outdoor adventures and romantic getaways. With its stunning beaches and scenic landscapes, visitors can indulge in water activities or enjoy a leisurely stroll along the shoreline. The area is home to several resorts and recreational spaces that provide a perfect backdrop for relaxation or fun-filled family outings. Music concerts and community events add a lively touch to the town, making Westbrook a charming place to explore and unwind.
  • Branford: Located 11.3km away from Guilford, Branford offers a picturesque setting for outdoor enthusiasts and those looking for a romantic escape. The town is well-known for its beautiful beaches and tranquil lakes, making it perfect for a day of swimming, picnicking, or simply soaking in the serene surroundings. Branford is also home to various recreational areas where you can enjoy hiking, skiing, or educational activities. The inviting atmosphere and natural beauty make Branford a must-visit for anyone wanting to experience the best of Connecticut's coastal charm.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly Low
February32.4°F (0.2°C)Light RainMostly SunnyAverage
March38.5°F (3.6°C)Light RainMostly SunnyAverage
April48.4°F (9.1°C)Light RainMostly SunnySlightly High
May58.3°F (14.6°C)Light RainMostly SunnyAverage
June66.9°F (19.4°C)Light RainMostly SunnySlightly High
July74.1°F (23.4°C)Light RainMostly SunnySlightly High
August73.2°F (22.9°C)Light RainMostly SunnyAverage
September66.7°F (19.3°C)Light RainMostly SunnyAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverage
November45.5°F (7.5°C)Light RainMostly SunnySlightly Low
December37.6°F (3.1°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Keen to save on your next holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Vrbo accommodation that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up from where you last stopped, and manage your travel arrangements. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/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)
  • 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 most popular type of holiday home accommodation in Guilford?
Houses are the most popular style of holiday home in Guilford, according to our data. Even if you've got something a little different in mind, Bookabach 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 home 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 Bookabach holiday homes 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 Bookabach and how many guests to view your home 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 homes 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 homes on Bookabach. 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 homes and you'll enjoy pool days every day. Simply enter your dates into Bookabach, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Guilford?
When it comes to home amenities that guests are on the lookout for in Guilford, a barbecue grill, a firepit and an ocean view rank highest. With Bookabach 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 homes 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 homes in Guilford that welcome kids?
Guilford has 30 family-friendly holiday homes to pick from. And tracking down a stay that welcomes kids is simple with Bookabach'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 homes 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 homes 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 Bookabach.
Are there holiday homes with WiFi in Guilford?
Pick from 15 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Guilford?
Select your dates and then use the filter tool to see holiday homes with air conditioning in Guilford on Bookabach. 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 home in Guilford?
The minimum age requirements can differ between properties on Bookabach, 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 home in Guilford for?
How long you can rent a holiday home 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.

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