Ashford Vacations from $180

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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.
Rodeway Inn Willington North

Rodeway Inn Willington North

2 out of 5
Price was $224, price is now $180 per person
$180
per person
Feb 18 - Feb 22
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
4.2/10 (976 reviews)
Air conditioning worked Great

Reviewed on Jan 11, 2026

Solano Inn

Solano Inn

2.5 out of 5
Price was $371, price is now $283 per person
$283
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (212 reviews)
Nice room. Friendly staff. Rooms could use extra outlets for phone, I-pad, etc.

Reviewed on Dec 1, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $327, price is now $258 per person
$258
per person
Feb 18 - Feb 22
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.2/10 Very Good! (1,002 reviews)
Friendly staff , coffee always available

Reviewed on Jan 2, 2026

Graduate by Hilton Storrs

Graduate by Hilton Storrs

4 out of 5
Price was $615, price is now $496 per person
$496
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Hartford (BDL)
9.4/10 Exceptional! (1,000 reviews)
The hotel is always clean and the service is always on point.

Reviewed on Dec 15, 2025

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
Price was $900, price is now $742 per person
$742
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
9.2/10 Wonderful! (1,002 reviews)
I arrived at 2 am and front desk was able to get me into a room at a great rate so I could get a few hours of sleep. Thank you!

Reviewed on Jan 4, 2026

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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
$62 nightly
The price is $72 total per night from Jan 12 to Jan 13
$72 total
Jan 12 - Jan 13
Total with taxes and fees
6.4/10 (351 reviews)
Clean room, great staff

Reviewed on Nov 3, 2025

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

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

Ashford CT
$263 nightly
The price is $298 total per night from Jan 15 to Jan 16
$298 total
Jan 15 - Jan 16
Total with taxes and fees
9/10 Wonderful! (26 reviews)
The cabin was perfect for our short holiday trip! It was warm and cozy. Would recommend it to a small family

Reviewed on Dec 29, 2025

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

Amazing lake house with everything you need!

Ashford CT
9.6/10 Exceptional! (23 reviews)
Enjoyed our stay, cute place.

Reviewed on Dec 27, 2025

Get rates
Amazing lake house with everything you need!
See all 292 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 $180 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.