Guilford Vacations from $517
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Your Guilford Vacation
Experience the unique character and personality of Guilford with a tailor-made Guilford vacation package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. There's plenty to include on your must-see list during your trip to Guilford, beginning with leading attractions such as Lowes Covered Bridge and Abbot Evangelical Free Church. Your dream Guilford vacation is just clicks away. Browse airfares, hotels and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Guilford Vacation Packages
- Iris Hotel Cape Cod
Jan 15 - Jan 18Iris Hotel Cape Cod + Flight
Falmouth3 nights3.0 star property8.4/10 - Very good (439 reviews)Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • Nonstop$839$517found 23 hours agoper traveler - Boston Lodge and Suites
Dec 21 - Dec 26Boston Lodge and Suites + Flight
Dorchester5 nights4.0 star property8.4/10 - Very good (194 reviews)"The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."Reviewed October 17, 2026Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • Nonstop$1,565$769found 1 day agoper traveler - Boston Harbor Hotel
Dec 21 - Dec 26Boston Harbor Hotel + Flight
North End5 nights5.0 star property9.8/10 - Exceptional (1,002 reviews)Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • Nonstop$2,418$1,457found 1 day agoper traveler - Battery Wharf Hotel, Boston Waterfront
Jan 7 - Jan 10Battery Wharf Hotel, Boston Waterfront + Flight
North End3 nights4.5 star property9.0/10 - Wonderful (2,075 reviews)Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • 1 stop$1,039$658found 2 days agoper traveler - Four Seasons Hotel Boston
Dec 23 - Dec 27Four Seasons Hotel Boston + Flight
Bay Village3 nights5.0 star property9.4/10 - Exceptional (495 reviews)Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • 2 stops$2,179$1,438found 1 day agoper traveler
Where to stay in and around Guilford
Abbot
Discover Abbot, a welcoming destination perfectly suited for outdoor enthusiasts and families seeking adventure and natural beauty. With attractions like Lake Hebron for serene views, the historic Lowe's Covered Bridge for a glimpse into the past, and nearby national parks offering hiking trails and recreational areas, Abbot provides a perfect backdrop for exploration. Located about 4 miles by car from Guilford, this charming city is a smart choice for your next vacation, ensuring a memorable stay immersed in nature and scenery.
Sangerville
Experience the charm of Sangerville, an excellent hub for family travelers and nature enthusiasts looking for a scenic getaway. This quaint city offers access to picturesque hiking trails and the stunning Peaks-Kenny State Park, perfect for outdoor adventures. Don't miss the historic Lowe's Covered Bridge, a must-see landmark. Located about 1 mile by car from Guilford, Sangerville provides a budget-friendly option for those wanting to immerse themselves in the beauty of Maine.
Dover-Foxcroft
If you are a family traveler, look no further than Dover-Foxcroft, which features stunning natural beauty and plenty of outdoor activities. With attractions like Peaks-Kenny State Park for hiking, the historic Lowe's Covered Bridge, and the serene Lake Wassookeag, this city offers an ideal backdrop for memorable adventures. Located about 8 miles by car from Guilford, Dover-Foxcroft is a smart choice for your stay, ensuring easy access to both relaxation and recreation.
Parkman
Parkman, nestled in Guilford, stands out as a prime spot for families and nature lovers interested in outdoor adventures and scenic beauty. Visitors can explore the nearby national park, enjoy hiking trails, or relax at the picturesque Brown Hill park. The charming Lowe's Covered Bridge adds a touch of history to your stay. With its seasonal appeal peaking from July to September, Parkman offers a refreshing escape for those seeking romance and adventure, making it a smart choice for your vacation lodging.
Willimantic
Travelers looking for a charming getaway will find Willimantic to be the ideal base for their vacation, featuring stunning natural scenery and outdoor activities. This village in Guilford invites families and budget-conscious adventurers to explore its nearby attractions, including the breathtaking Borestone Mountain, serene Lake Hebron, and the expansive Peaks-Kenny State Park. With visitor numbers peaking from July to September, Willimantic offers a vibrant atmosphere during the summer months, making it a smart choice for your stay.
Discover the most popular places to visit in Guilford
Guilford Hotel Deals
"Beautiful home. Gracious hosts. Enjoyed our stay."
"You will receive the best service and the utmost kindness—the very best."
"So nice with a delicious breakfast every morning."
"Location view and balcony... Awesome Didn't like king size mattress was worse than sleeping on the ground..."
"Excellent location. It's our camp without the maintenance!"
"For those of us who still have traditional tv.....cable or satellite, it's very difficult to figure out how to use the tv with Roku or Netflix or whichever. All I wanted was a tv guide and ended up watching Leave It To Beaver all night."
Frequently Asked Questions
How much does a Guilford vacation package cost?
Offering excellent value package deals from $517 on Expedia, you'll be surprised at how little a vacation to Guilford costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Guilford?
If you'd like to snag a cheap Guilford vacation package, consider traveling in October, November and December. You're likely to find better rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Guilford?
The ideal duration for your Guilford vacation depends on what you'd like to do. Generally, a handful of days to a week will give you time to hit all the main sights and explore some hidden treasures along the way.
How to find the best Guilford package deals?
Begin your search for a Guilford package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Guilford package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Guilford escape underway.
Is it cheaper to book a Guilford vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Guilford vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Guilford?
If you're planning a spontaneous Guilford adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Guilford vacation packages?
Your Guilford trip is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.