Winslow Vacations from $267

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Your Winslow Vacation

Take the worry out of organizing your next grand adventure with a Winslow vacation package. Whether you're visiting for its cuisine, history, art or other highlights, you'll find countless exciting experiences to delve into. Every trip to Winslow needs a well-designed itinerary. Fill yours with leading attractions like Colby College, Waterville Opera House and Thomas College. Your dream Winslow vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Winslow vacation packages

Price found within the past 48 hours. Click for updated prices.
Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

2.5 out of 5
Price was $317, price is now $267 per person
$267
per person
Jan 15 - Jan 18
found 8 hours ago
Roundtrip flight included
New York (JFK) to Augusta (AUG)
9/10 Wonderful! (463 reviews)
The Inn was very pleasant. All the rooms on the second level had balconies with lovely views of the town and river. The staff were very friendly and there was plenty of parking.

Reviewed on Nov 4, 2025

Jordan Hotel

Jordan Hotel

3 out of 5
Save 100% on your flight
Price was $599, price is now $448 per person
$448
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Augusta (AUG)
8.8/10 Excellent! (411 reviews)
Staff were very courteous and super friendly. Exterior is beautifully surreal as well as the main lobby. Interior rooms were a little outdated but kept clean. Zero complaints from my stay. Only slight issue was that the breakfast/ coffee shop was not up to par for my liking. Pool / Spa area was kept clean as well as the Sauna and Steam room. Super plus on the amenities. Would highly recommend a stay if you are in the area.

Reviewed on Nov 7, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
Price was $366, price is now $285 per person
$285
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Augusta (AUG)
8.2/10 Very Good! (1,009 reviews)
Clean room. All personnel was friendly and very helpful. The breakfast was good, had all the things we wanted. Free cookies! Overall, a great experience and close to all stores. Thanks for a great stay!

Reviewed on Nov 9, 2025

My Valhalla Farm

My Valhalla Farm

3.5 out of 5
Price was $586, price is now $463 per person
$463
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Augusta (AUG)
No reviews
Stone Park

Stone Park

4 out of 5
Price was $354, price is now $299 per person
$299
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Augusta (AUG)
9.2/10 Wonderful! (167 reviews)
My wife and I have been here several times and loved it

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Winslow

Sunsets in Colby

Colby College

4.5/5(37 reviews)

Explore the campus of Colby College, during your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Colby College

Waterville Opera House

4.5/5(7 reviews)

You can get tickets for a performance at Waterville Opera House on your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Waterville Opera House

Thomas College

4.5/5(2 reviews)

Explore the campus of Thomas College, during your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Thomas College

Winslow Hotel Deals

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundable
$134 nightly
The price is $146 total per night from Nov 16 to Nov 17
$146 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Staff was excellent, and the property was in a great shape

Reviewed on Nov 9, 2025

Maine Evergreen Hotel, an Ascend Collection Hotel
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave, Augusta, ME
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $119 total per night from Nov 16 to Nov 17
$119 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Room was clean and quiet. Restaurant menu was pretty limited.

Reviewed on Nov 9, 2025

Senator Inn & Spa
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $122 total per night from Dec 6 to Dec 7
$122 total
Dec 6 - Dec 7
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
Convenient on/off highway. Shopping nearby, attached to a reputable restaurant that is accessed from a corridor. Comfy bed, gas fireplace. A good nights rest!

Reviewed on Nov 8, 2025

Fireside Inn & Suites Waterville
See all 437 properties in Winslow
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 Winslow Vacation Packages

Winslow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Augusta State Airport (AUG)
Population
7,800
Top Sights
First Congregational Church, Colby College and Waterville Opera House

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Frequently asked questions

How much does a Winslow vacation package cost?
Offering great value package deals from $267 on Expedia, you'll be pleasantly surprised at how much a vacation to Winslow costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Winslow?
If you'd like to book a cheap Winslow vacation package, consider visiting in November, December and January. You'll typically find lower rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Winslow?
With a well-organized schedule, you can easily tick off the top Winslow sights in a few days. But if you want to discover hidden gems or go on day tours, consider booking your Winslow vacation for longer.
How to find the best Winslow package deals?
Bagging a cheap Winslow package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Winslow package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Winslow vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize your Winslow getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winslow?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winslow adventure.
Does Expedia offer Book Now, Pay Later Winslow vacation packages?
Jet off on your perfect escape to Winslow with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up bargains while they last.

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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.