Leicester Vacations from $543

Book a Hotel + Flight or Car together to unlock savings

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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $625, price is now $543 per person
$543
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (821 reviews)
Beautiful setting with our room directly on the lake.

Reviewed on Sep 28, 2025

Summit Lodge

Summit Lodge

3 out of 5
Price was $902, price is now $785 per person
$785
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
8.6/10 Excellent! (390 reviews)
A unique, older building with a funky layout. Great outdoor space including pool, fire pit, plunge pool and plenty of outdoor seating. Inside includes a pub (upstairs and down) and hot tub. Staff are friendly. Some restaurants and markets are within a 3-5 minute drive if needed.

Reviewed on Sep 15, 2025

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

2 out of 5
Save 100% on your flight
Price was $3,613, price is now $3,155 per person
$3,155
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

2 out of 5
Save 100% on your flight
Price was $12,470, price is now $10,964 per person
$10,964
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $878, price is now $773 per person
$773
per person
Dec 15 - Dec 18
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Best place in Killington!

Reviewed on Sep 30, 2025

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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
$167 nightly
The price is $187 total per night from Oct 1 to Oct 2
$187 total
Oct 1 - Oct 2
Total with taxes and fees
10/10 Exceptional! (61 reviews)
"Incredible spot! Beautiful setting, quaint and well thought out spaces with the joy of playing piano over your morning coffee."

Reviewed on Sep 8, 2025

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

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
$199 nightly
The price is $219 total per night from Oct 26 to Oct 27
$219 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
"Enjoyed the stay"

Reviewed on Sep 19, 2025

Middlebury Inn
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
$132 nightly
The price is $145 total per night from Oct 20 to Oct 21
$145 total
Oct 20 - Oct 21
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"The room was very clean and comfortable."

Reviewed on Sep 18, 2025

Comfort Inn Rutland - Killington
See all 649 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.

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Frequently asked questions

How much does a Leicester vacation package cost?
Offering great value package deals from $543 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.