Leicester Vacations from $660

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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.

The Latest Leicester vacation packages

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

Chateau Rooms

4.5 out of 5
Price was $842, price is now $660 per person
$660
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
9.2/10 Wonderful! (62 reviews)
We've stayed here 3x now. (1) stay in each of the room options available. You can't beat the lake front rooms. But the 3rd room in the back is nice and cozy. Will absolutely be back next summer and fall. Our only wish is that the fireplace didn't have such a short timer on it. It only stays on for 15 minutes and then shuts off. Hard to get it on as well. It must have some type of thermostat sensor or something. But quite frustrating on a cool fall day when you just want the warm glow of a fire for extended stay.

Reviewed on Oct 20, 2025

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Save 100% on your flight
Price was $2,107, price is now $1,813 per person
$1,813
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
9.8/10 Exceptional! (16 reviews)
Amazing castle! Beautiful views of Lake George. Your own private hidden getaway. The most unique experience in Lake George.

Reviewed on Jul 5, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,129, price is now $1,046 per person
$1,046
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Great place to stay! The balcony was definitely nice to have as an option. The Mountain View were phenomenal. Highly recommend staying at this facility.

Reviewed on Oct 18, 2025

Sugar Hollow in Chittenden

Sugar Hollow in Chittenden

2 out of 5
Price was $4,467, price is now $4,162 per person
$4,162
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
No reviews
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $3,159, price is now $2,946 per person
$2,946
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rutland (RUT)
No reviews
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Discover the most popular places to visit in Leicester

Otter Creek

Commune with nature and explore the great outdoors at Otter Creek during your travels in Brandon. Discover the mountain views while you're in the area.

Otter Creek

Neshobe Golf Club

Enjoy a round of golf in Brandon at Neshobe Golf Club. Discover the mountain views while you're in the area.

Neshobe Golf Club

Brandon Music

You can spend an afternoon studying the exhibits at Brandon Music during your travels in Brandon. Discover the mountain views while you're in the area.

Brandon Music

Leicester Hotel Deals

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester
$149 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
10/10 Exceptional! (63 reviews)
The place was amazing. So well appointed and exactly as described.

Reviewed on Oct 5, 2025

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Nov 11 to Nov 12
$121 total
Nov 11 - Nov 12
Total with taxes and fees
8/10 Very Good! (1,023 reviews)
The room only had one chair. A second chair for a two person room or a couch would have been nice.

Reviewed on Oct 14, 2025

Comfort Inn Rutland - Killington
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Nov 17 to Nov 18
$141 total
Nov 17 - Nov 18
Total with taxes and fees
8.8/10 Excellent! (1,023 reviews)
At age 77 I found the multiple sets of stairs a challenge.

Reviewed on Oct 20, 2025

Middlebury Inn
See all 645 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.

Find the Best Leicester Vacation Packages

Leicester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
1,100
Top Sights
Neshobe River Winery, Brandon Museum and Otter Valley Winery

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Frequently asked questions

How much does a Leicester vacation package cost?
Offering great value package deals from $660 on Expedia, you'll be surprised at how little a vacation to Leicester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Leicester?
You're likely to find reduced prices and better availability in September, October and December. Check out our cheap Leicester vacation packages and you could get some great off-season discounts.
How many days is enough for Leicester?
Typically, a handful of days is enough to visit the major sights during your Leicester vacation. But if you'd like to have more time to relax or go on day tours, think about extending your trip.
How to find the best Leicester package deals?
Landing a cheap Leicester package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Leicester package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Leicester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Leicester vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Leicester?
If you're considering a spontaneous Leicester getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Leicester vacation packages?
Set off on your dream trip to Leicester with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.