Guilford Holidays
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Top hotels in Guilford
Spark by Hilton Guilford
300 Boston Post Rd Guilford CT
Fully refundableReserve now, pay when you stay
Rp1.874.815
Rp2.156.037 total
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (203 reviews)
"We stayed at five different hotels on our trip and the front desk host Kush was by far the most friendliest and most helpful. We enjoyed our stay."
Reviewed on 3 Sept 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
Rp2.368.170
Rp2.723.440 total
30 Sept - 1 Oct
includes taxes & fees
Sound View Greenport
58775 County Rd 48 Greenport NY
Rp5.159.700
Rp7.406.530 total
28 Sept - 29 Sept
includes taxes & fees
8.4/10 Very good! (717 reviews)
"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city ..."
Reviewed on 7 Sept 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Guilford attractions
Guilford Town Green
The Guilford Town Green, one of New England's largest historic commons, offers shade trees perfect for relaxation. Explore surrounding boutiques or time your visit for farmers' markets and summer concerts.
Bishops Orchard and Winery
8.4/10 (11 reviews)
This historic family farm has cultivated Connecticut's finest fruits since 1871. Sample estate-made wines, pick seasonal berries, or browse the market's fresh produce and artisanal goods.
Chaffinch Island State Park
9.6/10 (4 reviews)
This serene 22-acre coastal park offers picturesque views of Long Island Sound and rocky shores to explore. Bring binoculars for exceptional birdwatching while enjoying the peaceful tidal pools and grassy picnic areas.
Sachem Head Harbor
This serene coastal harbour showcases New England's maritime heritage with its historic yacht club dating to the 19th century. Enjoy panoramic water views while watching sailboats glide across the picturesque bay.
Henry Whitfield State Museum
10.0/10 (3 reviews)
Built in 1639, this stone house stands as Connecticut's oldest dwelling and New England's oldest stone home. Explore three floors of period furnishings that showcase nearly four centuries of fascinating American history.
Guilford Art Center
9.2/10 (5 reviews)
This creative hub offers classes in ceramics, blacksmithing, painting, and jewellery making for all skill levels. Explore the gallery's rotating exhibits or find unique handcrafted treasures in the artisan shop.
Hyland House Museum
8.8/10 (3 reviews)
This beautifully preserved 1713 saltbox house showcases colonial life through period furnishings. Guided tours reveal historical details while surrounding gardens complement your journey.
Medad Stone Tavern Museum
Find out about the history of Guilford when you take a trip to Medad Stone Tavern Museum. While in this family-friendly area, you can enjoy the restaurants.
Frequently asked questions
How much does a Guilford holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Guilford costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Guilford?
You can typically find lower prices and better availability in January, February and March. Browse our cheap Guilford holiday packages and you could land some excellent off-season deals.
How many days is enough for Guilford?
Generally, a handful of days is ideal for a Guilford holiday. With a well-organised itinerary, you can go to all the leading attractions including Hyland House Museum, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Guilford?
Whether you're planning to explore attractions like Bishops Orchard and Winery and Guilford Art Centre, or eager to experience its terrific nature and history, a Guilford holiday is sure to exceed your expectations. Book your getaway with Expedia and discover why Guilford is such a good holiday destination.
How to find the best Guilford package deals?
Use Expedia's handy filters to find some fabulous Guilford package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Guilford package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Guilford holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging accommodation and flights separately. Better still, you can customise your Guilford escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Guilford?
If you have your Guilford holiday dates locked in, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Guilford?
- Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the available activities will also help you decide when to holiday in Guilford.
- Calculate your budget: Ensure you have enough money to cover everything from food and transportation to flights and activities. Your accommodation will probably be the biggest expense during your trip to Guilford.
- Decide your trip length: Think about how long you'd like to spend exploring Guilford. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Guilford holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
