Winchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,244, price is now CA $1,085 per person
CA $1,085
per person
Jun 1 - Jun 6
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8/10 Very Good! (222 reviews)
Great location. Staff slow to respond.
Reviewed on Feb 21, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,362, price is now CA $1,144 per person
CA $1,144
per person
Jun 1 - Jun 6
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,500, price is now CA $1,275 per person
CA $1,275
per person
Jun 1 - Jun 6
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) 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
Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
Price was CA $1,364, price is now CA $1,174 per person
CA $1,174
per person
Jun 1 - Jun 6
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) 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
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was CA $1,281, price is now CA $1,112 per person
CA $1,112
per person
Jun 1 - Jun 6
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 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 Apr 27 to Apr 28
CA $199
CA $222 total
Apr 27 - Apr 28
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Bathroom should have a safety grab bar in the shower as well as hooks for towels.
Reviewed on Apr 5, 2026
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
6.8/10 (1,004 reviews)
Eletric was out without. Found a note on door at check.in to call and they said no information if reopening. Man was pleasant not his fault he is employee. had to find another place that night. Expedia helped.
Reviewed on Apr 10, 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Apr 22 to Apr 23
CA $164
CA $181 total
Apr 22 - Apr 23
includes taxes & fees
8.2/10 Very Good! (956 reviews)
Nice
Reviewed on Mar 29, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
