Rochester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Rochester

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$634 per night from 1 Sept to 2 Sept
S$634
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (802 reviews)
Get away to Vermont
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."

Reviewed on 14 Aug, 2025

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The Shire Woodstock
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is S$204 per night from 24 Aug to 25 Aug
S$204
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Convenient and affordable inn"

Reviewed on 14 Aug, 2025

Middlebury Inn
See all 2,015 properties in Rochester
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.

Frequently asked questions

How much does a Rochester holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Rochester costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Rochester?
January, February and March are great times to search for cheap Rochester holiday packages. Opting to travel in quieter months means you can usually find lower prices on accommodation and flights.
How many days is enough for Rochester?
The ideal length of your Rochester holiday depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to hit all the top attractions and discover some hidden treasures along the way.
How to find the best Rochester package deals?
Use Expedia's filters to find some terrific Rochester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Rochester package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Rochester holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the freedom to create a customised Rochester holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Rochester?
If you have your Rochester travel dates finalized, book early to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Rochester?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Rochester.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodation will probably be the largest expense during your trip to Rochester.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Rochester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Rochester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.