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.
Mountaineer Inn
Price was CA $1,555, price is now CA $1,402 per person
CA $1,402
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Nanaimo (YCD) to Springfield (VSF)
8.8/10 Excellent! (503 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.
Reviewed on Aug 23, 2025
Chalet 239
Price was CA $1,595, price is now CA $1,473 per person
CA $1,473
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Nanaimo (YCD) to Springfield (VSF)
9.4/10 Exceptional! (74 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept.
The free breakfast was a plus.
Reviewed on Aug 12, 2025
Mount Snow Grand Summit Resort
Price was CA $1,568, price is now CA $1,490 per person
CA $1,490
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Nanaimo (YCD) to Springfield (VSF)
8.6/10 Excellent! (220 reviews)
Our room was clean and comfortable .The hot tub, sauna and heated pool were very enjoyable. Staff was kind and responsive. Amazing location!
Reviewed on Sep 6, 2025
Winchester Hotel Deals
The Colonial Hotel
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Sep 11 to Sep 12
CA $199
CA $222 total
Sep 11 - Sep 12
includes taxes & fees
Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
The price is CA $187 per night from Sep 17 to Sep 18
CA $187
CA $205 total
Sep 17 - Sep 18
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Sep 16 to Sep 17
CA $173
CA $187 total
Sep 16 - Sep 17
includes taxes & fees
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.
