Leicester Vacations from $444
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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.
Bentley House Bed and Breakfast
Price was $510, price is now $444 per person
$444
per person
Oct 16 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
10/10 Exceptional! (2 reviews)
Beautiful old building, well-maintained, filled with vintage furniture and collectable items. Like staying in a museum. Owners are very friendly and helpful. Breakfast was great.
Reviewed on Jul 26, 2026
Align Inn Vermont
Price was $724, price is now $605 per person
$605
per person
Oct 16 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.4/10 Exceptional! (1,256 reviews)
It's not glamorous but it's clean, maintained and the staff are very kind and helpful. The location is great, with easy access to local towns, the state park and anything we could need.
Reviewed on Jul 24, 2026
Golden Stage Inn B&B
Price was $963, price is now $833 per person
$833
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rutland (RUT)
10/10 Exceptional! (45 reviews)
Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!
Reviewed on Jul 6, 2026
Greenbrier Inn
Price was $697, price is now $620 per person
$620
per person
Oct 16 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.4/10 Exceptional! (684 reviews)
The hotel was very nice, quaint and clean. It is in a great location just prior to the entry of the access road. Large room. Small hotel with only about 20 rooms. Breakfast included. I would recommend a stay.
Reviewed on Jul 16, 2026
Stay near popular Leicester attractions
Leicester Hotel Deals
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester VT
$170 nightly
The price is $190 total per night from Jul 28 to Jul 29
$190 total
Jul 28 - Jul 29
Total with taxes and fees
10/10 Exceptional! (82 reviews)
"Overall, the place was quite inviting and very clean. In terms of sleeping arrangements, the mattress upstairs was very comfortable. I truly only used this property as sleeping accommodations for my annual weeklong family reunion at Branbury State Park as I am no longer able to camp for health reasons. ..."
Reviewed on Jul 25, 2026
Middlebury Inn
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $166 total per night from Jul 27 to Jul 28
$166 total
Jul 27 - Jul 28
Total with taxes and fees
9/10 Wonderful! (1,012 reviews)
"The staff was very nice and answered any question we had. The rooms were very clean and well stocked. If we couldn't find it in the room the staff got it for us. The tavern food was delicious and the wait staff very pleasant. We needed gluten free meals and they made it happen."
Reviewed on Jul 25, 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
$123 nightly
The price is $135 total per night from Jul 29 to Jul 30
$135 total
Jul 29 - Jul 30
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"Great, quiet, clean hotel. Great breakfast too!"
Reviewed on Jul 25, 2026
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.