Middlebury Vacations from $599
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
The Latest Middlebury Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Bertram Inn at Glenmoor
$599
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Akron (CAK)
8.6/10 Excellent! (324 reviews)
We had a wonderful stay. Went to country fest nearby and it was an easy drive. Good food and friendly staff. Would stay again.
Reviewed on Aug 17, 2026
Holiday Inn Canton (Belden Village) by IHG
$785
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Akron (CAK)
8.2/10 Very Good! (592 reviews)
We had a couple issues with the rooms, but the staff took immediate care of the problems. We liked the proximity to activities and venues. We had a great few days there!!
Reviewed on Aug 29, 2026
Where to stay in Middlebury
Find the best Middlebury areas and neighborhoods for the activities you enjoy most. Learn more about Middlebury
Downtown Akron
4 out of top 10 points of interest in this area
Downtown Akron is noteworthy for its restaurants, and you can make a stop at top attractions like Canal Park and EJ Thomas Hall.
Merriman Valley
While visiting Merriman Valley, you might make a stop by sights like Cuyahoga Valley National Park and Cuyahoga River.
West Akron
1 out of top 10 points of interest in this area
While visiting West Akron, you might make a stop by sights like Akron Zoo and Perkins Park.
Northwest Akron
1 out of top 10 points of interest in this area
While visiting Northwest Akron, you might make a stop by sights like Cuyahoga Valley National Park and Stan Hywet Hall and Gardens.
Fairlawn Heights
If you're looking for some top things to see and do in Fairlawn Heights and surrounding area, you can visit Summit Mall and Stan Hywet Hall and Gardens.
Middlebury Hotel Deals
Hilton Garden Inn Akron
1307 E. Market Street Akron OH
Fully refundableReserve now, pay when you stay
$130 nightly
$150 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"The power went out for the whole night so the elevators didn’t work and we had the climb the stairs tv was out as well as some lights"
Reviewed on Aug 25, 2026
Courtyard by Marriott Canton
4375 Metro Cir Nw Canton OH
Fully refundableReserve now, pay when you stay
$101 nightly
$117 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Nice bar and lobby with tvs and game tables"
Reviewed on Aug 29, 2026
La Quinta Inn & Suites by Wyndham Cleveland Macedonia
268 East Highland Rd Macedonia OH
Fully refundableReserve now, pay when you stay
$78 nightly
$90 total
Sep 7 - Sep 8
Total with taxes and 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.