Colchester Vacations from $370

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Your Colchester Vacation

Amazing adventures await when you reserve a Colchester vacation package. Whether you're a history buff, foodie or just a traveler who loves to discover new places, there's something for everyone in this exciting city. You'll want to do some exploring during your trip to Colchester. Drop by popular attractions like Coopers Hawk Vineyards, Sprucewood Shores Estate Winery and Colio Estate Winery. Stop dreaming and start doing. Browse the multitude of options on Expedia today and finally put your Colchester vacation plans into gear!

The Latest Colchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
Downtown Windsor
Price was $392, price is now $370 per person
$370
per person
Dec 20 - Dec 22
found 6 hours ago
Roundtrip flight included
Greensboro (GSO) to Windsor (YQG)
8/10 Very Good! (1,002 reviews)
The first room we checked into had a toilet that leaked and the AC/Heat unit was not working. Initially they sent maintenance to resolve it. The repair could not be completed immediately so they moved us to another room and comped us our parking for the inconvenienve. The second room was great.

Reviewed on Nov 3, 2025

Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
City Centre
Price was $465, price is now $422 per person
$422
per person
Dec 20 - Dec 22
found 6 hours ago
Roundtrip flight included
Greensboro (GSO) to Windsor (YQG)
8.6/10 Excellent! (3,091 reviews)
Outstanding service.

Reviewed on Nov 3, 2025

Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
Downtown Windsor
Price was $439, price is now $404 per person
$404
per person
Dec 20 - Dec 22
found 6 hours ago
Roundtrip flight included
Greensboro (GSO) to Windsor (YQG)
8.6/10 Excellent! (1,348 reviews)
Room was great - waterfront view amazing! Great breakfast, overall the hotel was amazing!!

Reviewed on Nov 3, 2025

Windsor Manor

Windsor Manor

4 out of 5
City Centre
Price was $454, price is now $419 per person
$419
per person
Dec 20 - Dec 22
found 6 hours ago
Roundtrip flight included
Greensboro (GSO) to Windsor (YQG)
No reviews
Hotel STRY

Hotel STRY

2 out of 5
Price was $544, price is now $516 per person
$516
per person
Dec 20 - Dec 22
found 6 hours ago
Roundtrip flight included
Greensboro (GSO) to Windsor (YQG)
9.8/10 Exceptional! (20 reviews)
Absoultely enjoyed our stay. Sucess is always based on attention to details, in any business, and every detail here is well thought out. Look forward to many more visits.

Reviewed on Oct 10, 2025

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Discover the most popular places to visit in Colchester

Cooper's Hawk Vineyards

You can enjoy a tasting or tour at Cooper's Hawk Vineyards during your travels to Town of Essex. Savor the area's wineries and restaurants.

Cooper's Hawk Vineyards

Sprucewood Shores Estate Winery

4/5(2 reviews)

You can enjoy a tasting or tour at Sprucewood Shores Estate Winery during your travels to Town of Essex. Discover the countryside while you're in the area.

Sprucewood Shores Estate Winery

North 42 Degrees Estate Winery

You can enjoy a tasting or tour at North 42 Degrees Estate Winery during your travels to Town of Essex. While in this relaxing area, you can savor the wineries and restaurants.

North 42 Degrees Estate Winery

What to do in Colchester

Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

$68
per adult
Roasting Experience at 14th Coffee Co
See all activities in Colchester

Colchester Hotel Deals

Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!

Harrow
9.8/10 Exceptional! (127 reviews)
As always the cottage was perfect. This is my fifth time renting from Denise and this time we brought friends who also loved the cottage. We ate at a local winery and went to Point Pelee national park. Lovely memories and great place to relax.

Reviewed on Sep 14, 2025

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Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!
Lake front escape - a quiet lake front cottage with easy access to the beach

Lake front escape - a quiet lake front cottage with easy access to the beach

Colchester
9.6/10 Exceptional! (97 reviews)
Monique's cottage is a very cute home with AMAZING views of the lake. It can't get better. It's exactly as per the listing. The sun room facing the lake was our favorite spot, besides the fire pit outside. The main bedroom overlooks the lake too. The home has all the amenities, one can ask for and ...

Reviewed on Sep 21, 2025

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Lake front escape - a quiet lake front cottage with easy access to the beach
Sippin' & Stylin' in Wine Country!

Sippin' & Stylin' in Wine Country!

Essex
9.8/10 Exceptional! (7 reviews)
Very clean property, good location. well appointed.

Reviewed on Sep 8, 2025

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Sippin' & Stylin' in Wine Country!
See all 230 properties in Colchester
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 Colchester Vacation Packages

Colchester Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Windsor Airport (YQG)
Top Sights
Sprucewood Shores Estate Winery, Coopers Hawk Vineyards and North 42 Degrees Estate Winery

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Frequently asked questions

How much does a Colchester vacation package cost?
Offering excellent value package deals from $370 on Expedia, you'll be surprised at how little a vacation to Colchester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Colchester?
You're likely to find lower prices and better availability in December, January and February. Check out our cheap Colchester vacation packages and you could land some great off-season deals.
How many days is enough for Colchester?
The ideal duration for your Colchester vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to go to all the leading attractions and discover some hidden spots along the way.
How to find the best Colchester package deals?
Use Expedia's filters to find some of the best Colchester package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Colchester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Colchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Colchester escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Colchester?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Colchester trip.
How to plan a trip to Colchester?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Colchester.
  2. Calculate your budget: Make sure you have enough money to cover everything from food and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Colchester.
  3. Use Expedia's trip planning tool to discover Colchester: Research every part of your trip to Colchester with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by making a list of all the attractions and activities you want to get to in Colchester. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Colchester vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Colchester has to offer. Find all the incredible things to do in Colchester with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Colchester vacation packages?
Your Colchester getaway should be an escape from your busy life, not a source of money worries. So to give you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.