Guilford Vacation Packages
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Your Guilford Vacation
Skip the hassle of planning your next amazing adventure with a Guilford vacation package. Whether you're in town for its landmarks, food or something else, there's a never-ending supply of new experiences to be had. Fill up your itinerary with tours of The Stone Church, Brattleboro Common and Tasha Tudor Museum, some of the attractions you should see during your trip to Guilford. Whoever you're traveling with and whatever your bank balance, your dream Guilford vacation is just clicks away with Expedia.
Top Guilford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Delamar West Hartford
CA $1,169
per person
Oct 29 - Oct 31
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
9.8/10 Exceptional! (1,006 reviews)
Room beautiful. We arrived very late, so the turn down service was very welcoming and room felt cosy. Staff were nonchalant, not particularly welcoming. Breakfast was ok, nothing special, particularly as the reviews rate the breakfast. Pastries were slightly stale. On check out I was struggling with two cases and shouted at by the housekeeper as I entered a cordoned off area where the floor had been recently washed. As I walked around I heard her very loudly say “do they not read?!!!” It was right at the front of the check out desk. Overall the Delamar is a lovely hotel in a superb location if you are visiting West Hartford, but didn’t feel particularly special. Btw, the lady on reception was nice and helpful, unfortunately I forget her name.
Reviewed on Aug 11, 2026
Sinclair Inn Bed and Breakfast
CA $1,653
per person
Nov 1 - Nov 7
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Springfield (VSF)
10/10 Exceptional! (119 reviews)
Everything about Sinclair Inn Bed and Breakfast was exceptional. Holly and Kyle were welcoming hosts the property is very well maintained and the gardens are beautiful with areas to sit and relax. Breakfast was delicious with a variety of options with fresh berries, yogurt and granola to build your own parfait, delicious quiche, fresh baked goods. And delicious cookies for Night time snack.
I would highly recommend this establishment for your next trip to the area.
Reviewed on Aug 10, 2026
Landing in Downtown Hartford Near Dunkin' Park
Downtown Hartford
CA $1,516
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hartford (BDL)
6/10 (2 reviews)
It says parking is included but I had to pay for parking every day. Front desk couldn’t fix it, the people she called didn’t fix it. Missed a work meeting because of the whole ordeal. Just the night is $24.
Reviewed on May 3, 2026
Ready to book your vacation to Guilford?
Guilford Hotel Deals
Vikings Villages Resort
360 Viking Village Drive Guilford VT
CA $190
CA $221 total
Sep 7 - Sep 8
includes taxes & fees
10/10 Exceptional! (224 reviews)
"We went just for a quiet night away and it surpassed my expectations. The cabins were wonderful and there was plenty to do to keep my teenagers entertained."
Reviewed on Aug 10, 2026
The Jelly Mill-A Peaceful River Retreat
Guilford VT
10/10 Exceptional! (72 reviews)
"Noela and Mike are the best hosts! This is our second time staying here and the house is always incredibly clean and has everything you might need. We love the sound of the river, the quiet location, and the nearby goats. We had a wonderful trip and would definitely come back."
Reviewed on Jul 21, 2026
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
Fully refundableReserve now, pay when you stay
CA $135
CA $150 total
Aug 23 - Aug 24
includes taxes & fees
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 Welcome Center
8.4/10 (5 reviews)
After visiting Guilford Welcome Center, make a plan to see the other sights and activities in Guilford. Discover the coffeehouses and its entertainment venues while you're in the area.
Fort Dummer State Park
7.4/10 (6 reviews)
You can take time to visit Fort Dummer State Park during your travels to Guilford. Discover the area's entertainment venues, or seek out its ski slopes.
Sweet Pond State Park
You can take time to visit Sweet Pond State Park during your travels to Guilford. Make some time to visit the shops while you're in the area.
What to do in Guilford
Vermont RT 100 App-Guided Driving Audio Tour
CA $24
per traveller
Mindful Forest Escape: Rebalance, reflect and connect
CA $133
per adult
Frequently asked questions
How much does a Guilford vacation package cost?
You can pick up a vacation package to this top destination from CA $924 on Expedia. However, how much your vacation to Guilford costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Guilford?
If you'd like to score a cheap Guilford vacation package, consider planning a trip in January, April and November. You'll generally find lower prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Guilford?
You can explore all the top sights in Guilford in a few days, including the must-see Brattleboro Bowl. If you're after an extended Guilford vacation, check out what sort of excursions and activities are available close by.
How to find the best Guilford package deals?
Landing a cheap Guilford package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Guilford package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
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, car rental and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have 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?
Enjoy incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Guilford getaway.
How to plan a trip to Guilford?
- Choose when to travel: Check your diary and get packing. Your favourite season and the available activities will also help you decide when to vacation in Guilford.
- Plan your budget wisely: In addition to the price of your stay, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Guilford.
- Decide how long to go for: Now that you know more about Guilford, you can work out the ideal length of your break. Create a rough plan and give yourself enough time to cover everything you want to see.
- Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Guilford vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
