Guilford, CT

Travel Guide

A coastal landscape with a lighthouse, beach, rocky outcrops, and a distant city skyline.
A sunset over a calm lake with a rocky shoreline.
A beach with waves gently lapping onto the shore.
A residential street with a red house, a white house with an American flag, and a tree-lined sidewalk.
A large, white, two-story house with a symmetrical facade, large windows, and a central entrance with a decorative arch.
Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
300 Boston Post Rd Guilford CT
$91 nightly
The price is $105 total per night from Nov 1 to Nov 2
$105 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Guilford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Spark by Hilton Guilford
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
$126 nightly
The price is $145 total per night from Oct 28 to Oct 29
$145 total
Oct 28 - Oct 29
Total with taxes and fees
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
New Haven Hotel
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
$70 nightly
The price is $80 total per night from Nov 1 to Nov 2
$80 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Sands State Park ...
Motel 6 Milford, CT
See all 1,779 properties in Guilford
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.
TREETOPS house! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12

TREETOPS house! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12

Guilford CT
Stay at this vacation home in Guilford. Enjoy free WiFi, private pools, and a garden. Popular attractions Medad Stone Tavern Museum and Chaffinch Island State ...
10/10 Exceptional! (53 reviews)
"This architectural gem of a house in leafy, laid-back Guilford, CT, was a great setting for a reunion of longtime friends. The five bedrooms were each handsome and comfortable. The big, well-equipped kitchen allowed various groups of us to prepare meals together, and the dining-room table seated ..."

Reviewed on Oct 8, 2026

TREETOPS house! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
9.4/10 Exceptional! (206 reviews)
"My boyfriend and I looooved our stay and plan to come back next year for 2 night!"

Reviewed on Oct 20, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (69 reviews)
"What a great place , hidden gem on North Fork! it would have been nice if the Resturant was opened. We will be back"

Reviewed on Oct 21, 2026

North Fork Resort
See all properties in Guilford
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

Sachem Head Harbor

You can learn about the history of Guilford with a visit to Sachem Head Harbor. While in this family-friendly area, you can enjoy the restaurants.
See properties

Frequently asked questions

Is Guilford worth visiting?
Guilford is worth visiting for its standout attractions, such as the historic Guilford Town Green and scenic Sachem Head Harbor. Travelers can also enjoy diverse dining options, including Italian and North American cuisine, and benefit from practical train access for easy arrivals and departures.
When is the best time to visit Guilford?
The best time to visit Guilford is from May through September, when the climate is most pleasant for exploring. For fewer crowds and better value, the quieter months of December through March are a good bet, offering cooler weather and a more relaxed atmosphere.
What is Guilford known for?
Guilford is known for its Guilford Town Green, a prominent landmark, and other sites like Sachem Head Harbor and the Guilford Art Center. Travelers can also find a strong Italian food culture, offering diverse dining options.
What is a good itinerary length for Guilford?
A good itinerary length for Guilford is one to two days to explore key highlights like the Guilford Town Green, Sachem Head Harbor, and the Guilford Art Center. An extended stay of three to four days allows travelers to enjoy more time at these attractions and savor the local Italian, North American, or European dining options.
How do you get around Guilford?
Guilford offers travelers convenient train service, with a stop directly at Guilford Station. This provides a straightforward way to get around. For exploring areas not covered by the train, rideshare services are also available, offering a flexible transportation option.
What are the top things to do in and around Guilford?
Guilford offers natural beauty, artistic exploration, and relaxing outdoor spaces for travelers to enjoy:

  • Stroll through the Guilford Town Green.
  • Visit Sachem Head Harbor.
  • Explore the Guilford Art Center.
  • Discover Chaffinch Island State Park.
  • Relax at the beach near Chaffinch Island State Park.

How do I plan a trip to Guilford?
To plan your trip to Guilford, search for places to stay and book flights in advance. You can reach Guilford by train, or consider a rental car for exploring further. Balance outdoor activities like Guilford Town Green and Sachem Head Harbor with indoor options such as Guilford Art Center, especially for weather flexibility.
What cuisines can you find in Guilford?
In Guilford you can find Thai cuisine, with dishes like Pad Thai, Green Curry, and Tom Yum soup. Travelers can also enjoy other options, including Italian, North American, and various Asian and Latin American flavors. The area also features coffee shops and speakeasy bars.
Can I book a refundable hotel in Guilford?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Guilford by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Guilford with Expedia?
Expedia makes it easier to plan your Guilford trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Guilford?
The best choice depends on your travel style. Hotels in Guilford can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Guilford trip on Expedia?
Once you've booked your Guilford trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Guilford trip?
Expedia offers customer support before, during, and after your Guilford trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Guilford?
If it's your first trip to Guilford, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Guilford hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Guilford hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Guilford

A snow-covered park with a decorated Christmas tree, a church with a steeple, and several buildings in the background.

Branford

A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Madison

A white building with a large American flag on the side.

Durham

A building with a white facade and columns, a church with a steeple, and a grassy area with trees.

North Branford

Explore a world of travel with Expedia