Winchester Vacation Packages
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Your Winchester Vacation
When a city stay is calling, answer it with a vacation package to Winchester. With all your travel needs organized before you leave, all you need to do here is focus on having a ball. If a sightseeing tour is on the to-do list during your trip to Winchester, look around leading attractions like Thomas Aquinas College, Pisgah State Park and Birch Point. Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester vacation plans into motion!
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort
Price was CA $1,428, price is now CA $1,304 per person
CA $1,304
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Springfield (VSF)
10/10 Exceptional! (195 reviews)
Super clean, staff very nice, cabins had kitchens and fireplace that were very nice, but the coffee maker did not work. Nice you could spend just one night but really once there you are going to want to spend at least two. No amenities like pool or gym but they did have the worlds smallest sheep. :) It would be nice if they had a couple of cabins with a jacuzzi tub for after a long drive. It was hard to get to but i think our GPS messed up and took us onto lots of gravel roads to get there so be careful.
Reviewed on May 19, 2026
Latchis Hotel
Price was CA $1,169, price is now CA $1,070 per person
CA $1,070
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Springfield (VSF)
8.6/10 Excellent! (883 reviews)
Great location downtown near good restaurants. The hotel is old and full of character and history. Microwave, good shower, many cable TV channels, refrigerator, elevator- all in good order. With a cinema and restaurant in the lobby. We watched a movie (The Sheep Detectives).
Reviewed on May 29, 2026
Hampton Inn Brattleboro
Price was CA $1,296, price is now CA $1,231 per person
CA $1,231
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Springfield (VSF)
8.2/10 Very Good! (978 reviews)
Great rooms, comfortable, clean, very modern. Friendly staff. Highly recommend!
Reviewed on May 30, 2026
Grand Summit Resort, A Vail Resorts Property
Price was CA $1,134, price is now CA $1,085 per person
CA $1,085
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Springfield (VSF)
8.6/10 Excellent! (268 reviews)
Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful
Reviewed on May 2, 2026
Winchester Hotel Deals
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Jun 30 to Jul 1
CA $207
CA $231 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Very helpful staff."
Reviewed on May 27, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Jun 2 to Jun 3
CA $156
CA $171 total
Jun 2 - Jun 3
includes taxes & fees
8.6/10 Excellent! (889 reviews)
"Great location downtown near good restaurants. The hotel is old and full of character and history. Microwave, good shower, many cable TV channels, refrigerator, elevator- all in good order. With a cinema and restaurant in the lobby. We watched a movie (The Sheep Detectives)."
Reviewed on May 29, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jun 14 to Jun 15
CA $175
CA $192 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (986 reviews)
"Great rooms, comfortable, clean, very modern. Friendly staff. Highly recommend!"
Reviewed on May 30, 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.
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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.
