Ashford Vacations from $472
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Your Ashford Vacation
With a vacation package to Ashford, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your getaway has been taken care of before you depart, so you can enjoy each moment experiencing this interesting city. Want some sightseeing ideas for your trip to Ashford? Chaplin Museum and Nickerson Park are two popular attractions here. Check out Expedia's extensive range of travel options and start organizing your ultimate vacation to Ashford today.
The Latest Ashford vacation packages
Price found within the past 48 hours. Click for updated prices.
Belden House & Mews
Litchfield Historic District
$1,687
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Pensacola (PNS) to Hartford (BDL)
9.4/10 Exceptional! (13 reviews)
The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far.
Reviewed on Oct 15, 2026
Stay near popular Ashford attractions
Tinkerville Brook Reserve
6.0/10 (1 review)
Explore the great outdoors at Tinkerville Brook Reserve, a lovely green space in Ashford. You can enjoy the coffeehouses while in the area.
Ashford Town Green
Explore the great outdoors at Ashford Town Green, a lovely green space in Ashford. While you're in the area, wander around the natural setting.
Westford Hills Distillery
You can take time to visit Westford Hills Distillery during your travels to Ashford. While you're in the area, wander around the natural setting.
Rankin Preserve
You can take time to visit Rankin Preserve during your travels to Ashford. While you're in the area, wander around the natural setting.
Langhammer Town Forest
You can take time to visit Langhammer Town Forest during your travels to Ashford. While you're in the area, wander around the natural setting.
Josias Byles Sanctuary
You can take time to visit Josias Byles Sanctuary during your travels to Ashford. While you're in the area, wander around the natural setting.
Fliegel Farm Woods
You can take time to visit Fliegel Farm Woods during your travels to Ashford. While you're in the area, wander around the natural setting.
Iron Mine Valley Preserve
You can take time to visit Iron Mine Valley Preserve during your travels to Ashford. While you're in the area, wander around the natural setting.
Ashford Hotel Deals
Ashford Motel
26 Ashford Motel Road Ashford CT
Fully refundableReserve now, pay when you stay
$73 nightly
$84 total
Oct 25 - Oct 26
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford CT
9/10 Wonderful! (41 reviews)
"Avoid this property."
Reviewed on Sep 27, 2026
Amazing lake house with everything you need!
Ashford CT
9.6/10 Exceptional! (38 reviews)
"Very nice cottage by the lake. We booked this home for UConn parents weekend and it was nice to get away from the scene for a bit."
Reviewed on Sep 27, 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.
Find the Best Ashford Vacation Packages
Ashford Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Worcester Regional Airport (ORH) |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Taylor Brooke Winery, Harrisville Golf Course and Woodstock Golf Course |
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Frequently asked questions
How much does an Ashford vacation package cost?
You'll find cheap prices from $472 on Expedia for your Ashford break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Ashford costs.
What are the cheapest months to go to Ashford?
If you'd like to book a cheap Ashford vacation package, consider planning a trip in October, November and December. You're likely to find better prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Ashford?
Usually, a handful of days is enough to explore the top attractions during your Ashford vacation. However, if you prefer to have some time to relax or go on day tours, consider extending your trip.
How to find the best Ashford package deals?
Landing a cheap Ashford package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Ashford package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Ashford vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Ashford getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Ashford?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Ashford trip.
Does Expedia offer Book Now, Pay Later Ashford vacation packages?
Secure your ideal getaway to Ashford with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snag great deals while they last.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
