Leicester Vacation Packages

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Your Leicester Vacation

Our vacation packages to Leicester provide endless opportunities to immerse yourself in new sights, sounds and sensations. And with all of the travel arrangements taken care of, you can kick back and enjoy your city adventure in the way that you deserve. Every trip to Leicester needs a well-planned itinerary. Fill yours with major attractions like Brandon Music, Otter Creek and Neshobe River Winery. Expedia can help you escape your routine. Tailor your vacation to Leicester to suit your travel style, whatever that may be.

Top Leicester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was CA $1,936, price is now CA $1,842 per person
CA $1,842
per person
Aug 12 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rutland (RUT)
9.2/10 Wonderful! (68 reviews)
The property is certainly unique, but you have to know certain things before booking. It’s run more like an Air abnb than a hotel. There’s no formal check-in or check-out process. If you arrive before 5 PM the restaurant will be closed and there will be no one to assist you or answer any questions. There are only three rooms total and they’re all located upstairs above the restaurant. If you can’t get your own bags up the outdoor staircase this may not be the place for you. An access code gets you into the vestibule that houses the three rooms. There’s a funky key system for the rooms as well. All that being said it’s a hidden oasis down a dirt path smack in the middle of Bolton Landing. The room we had was spacious and well appointed, as was the bathroom with huge walk-in shower. Excellent water pressure as well, always a welcome treat. Although there are more dramatic views of the mountains and the lake from other vantage points, it feels very serene and tucked away. An added treat is the restaurant Chateau on the Lake. Fine dining with wonderful food, wine list, ambiance and staff—without the stuffiness.

Reviewed on Jul 12, 2026

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Leicester Hotel Deals

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester VT
The price is CA $188 per night from Aug 2 to Aug 3
CA $188
CA $295 total
Aug 2 - Aug 3
includes taxes & fees
10/10 Exceptional! (81 reviews)
"The place is really, really nice. Very nicely decorated and well appointed. Everything is very intentional- every electric socket and light switch exactly where you need it. The bed is very comfortable and bathroom is great. Very relaxing."

Reviewed on Jun 27, 2026

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jul 27 to Jul 28
CA $192
CA $212 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Very nice property and within walking distance of restaurants and shops. Their restaurant was quite good with reasonably priced options and drinks. We sat outside on the deck, which was great. Room was very nice and bed was comfortable. Could use extra sleeping pillows. The bathroom could be upgraded ..."

Reviewed on Jul 12, 2026

Middlebury Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
The price is CA $173 per night from Jul 26 to Jul 27
CA $173
CA $191 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"Staff was very friendly. The room was very clean and the breakfast was very nice overall always a very pleasant stay"

Reviewed on Jul 9, 2026

Comfort Inn Rutland - Killington
See all 691 properties in Leicester
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Stay near popular Leicester attractions

Leicester Town Hall

Leicester Town Hall is just one of the places to see in Leicester, so why not enjoy the other things to explore during your travels?
See properties

Frequently asked questions

How much does a Leicester vacation package cost?
Offering great value package deals from CA $1,842 on Expedia, you'll be pleasantly surprised at how much a vacation to Leicester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Leicester?
To pick up cheap Leicester vacation packages, plan your getaway outside of peak periods like public holidays and major festivals. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Leicester?
With a well-organized travel plan, you can easily visit the top Leicester attractions in a handful of days. But if you want to explore off the beaten track or take day trips, think about booking your Leicester vacation for longer.
How to find the best Leicester package deals?
Begin your search for a Leicester package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Leicester package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Leicester escape underway.
Is it cheaper to book a Leicester vacation as a package?
You can enjoy significant savings on your next Leicester escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Leicester?
If you have your Leicester vacation dates confirmed, book as soon as you can to grab 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 great for setting off on a whim.
How to plan a trip to Leicester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Leicester.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Leicester.
  3. Decide your trip length: Think about how long you want to spend discovering Leicester. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Leicester vacation package for you.

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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.