Chester Vacation Packages

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Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Rochester – Mayo Clinic Area by IHG

Hotel Indigo Rochester – Mayo Clinic Area by IHG

3.5 out of 5
Downtown Rochester
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
8.8/10 Excellent! (787 reviews)
Location was perfect for what we were doing. Room clean and nice. Coffee maker didn’t work. Parking convenient but not free.

Reviewed on Jul. 28, 2025

Broadway Plaza, Trademark Collection by Wyndham

Broadway Plaza, Trademark Collection by Wyndham

3 out of 5
Downtown Rochester
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
9.2/10 Wonderful! (156 reviews)
Kitchen was good for an extended stay. We were here for almost 3 weeks. It was more convenient to be able to prepare our own meals instead of going out for each. The skywalks made the walk to the clinic easy so we did not have to rent a car, worry about parking and we saved a lot of money by dping that. It also provided us with a good workout going back and forth. The staff was friendly and always helpful. We will come back again.

Reviewed on Jul. 10, 2025

Aspen Select

Aspen Select

3.5 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
8.6/10 Excellent! (1,000 reviews)
It was in a great location. Staff was wondering and accomodating.

Reviewed on Jul. 29, 2025

The Towers At Kahler Grand Hotel

The Towers At Kahler Grand Hotel

4 out of 5
Downtown Rochester
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
9.4/10 Exceptional! (84 reviews)
Great place to stay if going to Mayo. You don’t have to go outside to get to the buildings at Mayo with the subway level. Food is good for 2 meals a day. There’s room service & deliveries from Instacart if needed for groceries or outside food/beverage source. Personalized concierge service is good. Our stay was 10 days - they accommodated our extended stay flawlessly. My only complaint is the room temperature everywhere; it can be stuffy moving place to place. Take a fan to cool off in your room.

Reviewed on Jun. 18, 2025

Hyatt House Rochester/Mayo Clinic Area

Hyatt House Rochester/Mayo Clinic Area

3 out of 5
Downtown Rochester
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
9.2/10 Wonderful! (960 reviews)
The room was clean and spacious, beds were comfortable and it had a little kitchenette. The parking garage was full, and we had to park on the street where we could see broken bottles and intoxicated people walking around. It wasn’t the safest area to leave a vehicle.

Reviewed on Jul. 12, 2025

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Chester Hotel Deals

Americas Best Value Inn & Suites Spring Valley

Americas Best Value Inn & Suites Spring Valley

2 out of 5
745 N Broadway St, Spring Valley, MN
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 30 to Jul 31
CA $131
CA $144 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very Good! (403 reviews)
"This was a clean, basic hotel that fit our needs fine. Good price, nice location."

Reviewed on Jul. 26, 2025

Americas Best Value Inn & Suites Spring Valley
AmericInn by Wyndham Osage

AmericInn by Wyndham Osage

2.5 out of 5
2212 Highway 218, Osage, IA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $166 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (253 reviews)
"The whole place was very clean. Good selection for breakfast."

Reviewed on Jul. 25, 2025

AmericInn by Wyndham Osage
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St,, Osage, IA
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Aug 28 to Aug 29
CA $81
CA $91 total
Aug 28 - Aug 29
includes taxes & fees
6.2/10 (29 reviews)
Decent room for a decent price.
"Quick check in which i like but not very friendly room was basic no frills but nice. Had a mini fridge and coffee maker. But alarm clock did not work and it’s not upgraded. I know it’s stupid but i forgot my charging square but most hotels have the lamps with usb ports. This one did not. It was quiet ..."

Reviewed on Jul. 24, 2025

Western Inn & Suites
See all 27 properties in Chester
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.
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $811 on Expedia for your Chester getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
You're likely to find lower prices and greater availability in January, February and November. Explore our cheap Chester vacation packages and you could land some great off-season deals.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to tick off all the leading sights and discover some hidden gems along the way.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Chester package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chester adventure off to a flying start.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can tailor your Chester trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you're considering an impromptu Chester adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Chester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to escape to Chester.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Chester.
  3. Decide how long to go for: Now that you know more about Chester, you can figure out the right length of your vacation. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Chester 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.