Ashford Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Ashford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing in Downtown Hartford Near Dunkin' Park
Downtown Hartford
CA $1,509
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
Sheraton Hartford Hotel at Bradley Airport
CA $1,671
per person
Oct 16 - Oct 19
found 3 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hartford (BDL)
9.2/10 Wonderful! (1,006 reviews)
Room was so hot because air was barely working. Water barely got lukewarm during shower. However room was clean and room service was quick and great.
Reviewed on Aug 10, 2026
Ready to book your vacation to Ashford?
Ashford Hotel Deals
Ashford Motel
26 Ashford Motel Road Ashford CT
Fully refundableReserve now, pay when you stay
CA $97
CA $117 total
Aug 16 - Aug 17
includes taxes & fees
6.6/10 (378 reviews)
"The bathroom, what's not as clean as I expected. The sheet had stains on it. And there was holes in the bathroom walls . Everything else was okay."
Reviewed on Aug 9, 2026
Amazing lake house with everything you need!
Ashford CT
9.6/10 Exceptional! (35 reviews)
"Overall this was a cute place to stay, but we had a couple of issuesFirst, the good: the lake was less than a minute from the front door, the water accessories were awesome, the lake was great to kayak on, the community was very cute & welcoming (yay for rainbow/BLM flags!), the house was very cute ..."
Reviewed on Aug 2, 2026
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford CT
CA $301
CA $567 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (37 reviews)
"Extremely responsive and helpful host-- no issues on our end! Great stay."
Reviewed on Aug 5, 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.
Stay near popular Ashford attractions
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.
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.
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.
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.
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.
Frequently asked questions
How much does an Ashford vacation package cost?
You'll find cheap prices from CA $1,509 on Expedia for your Ashford break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Ashford costs.
What are the cheapest months to go to Ashford?
January, March and December are great times to look for cheap Ashford vacation packages. Travelling in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Ashford?
With a well-organized itinerary, you can easily visit the most popular Ashford attractions in a handful of days. But if you want to explore off the beaten track or take day trips, think about booking your Ashford vacation for longer.
How to find the best Ashford package deals?
Landing a cheap Ashford package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize 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 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 generally lower.
Is it cheaper to book an Ashford vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Ashford vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Ashford?
If you've got your Ashford vacation dates locked in, book as soon as you can to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Ashford?
- Choose your travel dates: The things you'd like to do in Ashford and your preferred season can help you decide when to go.
- Plan your budget wisely: In addition to the price of your stay, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Ashford.
- Determine how many days away: Start by compiling a list of the activities and sights you want to get to in Ashford. Then, estimate how long you'll need for each, including any travel time.
- Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Ashford 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.
