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.
Deerfield Valley Inn
Price was CA $1,085, price is now CA $1,001 per person
CA $1,001
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (118 reviews)
Way overpriced . I’ve stayed in other hotels in the area that included breakfast with hot tubs that are 50% less than this place. The place to put your shoes in the room had mud all over it. Maybe clean it before your next guest.
Reviewed on Mar 2, 2026
Stone Hearth Inn and Eatery
Price was CA $1,567, price is now CA $1,343 per person
CA $1,343
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (118 reviews)
Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking.
Reviewed on Mar 29, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,370, price is now CA $1,256 per person
CA $1,256
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.
Reviewed on May 17, 2026
Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
Price was CA $1,499, price is now CA $1,393 per person
CA $1,393
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know
Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.
Reviewed on Oct 8, 2025
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,461, price is now CA $1,359 per person
CA $1,359
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Winchester Hotel Deals
The Colonial Hotel
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from May 25 to May 26
CA $198
CA $221 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Over priced for the accommodation We stayed there because of a wedding, the ballroom next to us was so loud and noisy that we couldn’t hear the ceremony That was really annoying"
Reviewed on May 19, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jun 7 to Jun 8
CA $174
CA $191 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (978 reviews)
"Staff were amazing !!! The continental breakfast turbed out like a meeting ground for all the travellers. Everyone was so friendly."
Reviewed on May 19, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from May 28 to May 29
CA $160
CA $176 total
May 28 - May 29
includes taxes & fees
8.6/10 Excellent! (883 reviews)
"Great"
Reviewed on May 19, 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.
