Ashford Vacations from $307

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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.
The Cromwell Inn

The Cromwell Inn

2.5 out of 5
Price was $366, price is now $307 per person
$307
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
7.4/10 Good! (45 reviews)
We were disappointed that we couldn’t use the exercise equipment. We are older folks and wanted to walk on the treadmill and couldn’t figure it out. Otherwise it was a lovely six day stay. Staff was exceptional in all ways! Breakfast was adequate with oatmeal and yogurt every day plus a nice sweet bite after. Coffee machine had a problem as did the drain in our bathroom (216). Everything else was great!

Reviewed on Oct 29, 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,348, price is now $992 per person
$992
per person
Dec 29 - Jan 2
found 12 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
9.8/10 Exceptional! (1,003 reviews)

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $736, price is now $609 per person
$609
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
8.6/10 Excellent! (1,004 reviews)
No fax machine set up for business.

Reviewed on Oct 28, 2026

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $659, price is now $564 per person
$564
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hartford (BDL)
8.4/10 Very Good! (1,202 reviews)

Howard Johnson by Wyndham Hartford South – Rocky Hill

Howard Johnson by Wyndham Hartford South – Rocky Hill

2 out of 5
Price was $401, price is now $348 per person
$348
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.2/10 Very Good! (1,001 reviews)

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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.
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Ashford Hotel Deals

Ashford Motel

Ashford Motel

2 out of 5
26 Ashford Motel Road Ashford CT
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $84 total per night from Nov 1 to Nov 2
$84 total
Nov 1 - Nov 2
Total with taxes and fees
Ashford Motel
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Ashford CT
9/10 Wonderful! (41 reviews)
"Avoid this property."

Reviewed on Sep 27, 2026

Get rates
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Amazing lake house with everything you need!

Amazing lake house with everything you need!

Ashford CT
Get rates
Amazing lake house with everything you need!
See all 321 properties in Ashford
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 $307 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.