Winslow Vacations from $563

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $671, price is now $563 per person
$563
per person
Dec 2 - Dec 5
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
9.6/10 Exceptional! (51 reviews)

Cozy Keyes Cottage-family-friendly Amazing Views

Cozy Keyes Cottage-family-friendly Amazing Views

3.5 out of 5
Save 100% on your flight
Price was $3,074, price is now $2,432 per person
$2,432
per person
Jan 18 - Jan 25
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Augusta (AUG)
No reviews

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was $1,633, price is now $1,343 per person
$1,343
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Augusta (AUG)
10/10 Exceptional! (1 review)
Very charming place with great breakfast and beautiful lake

Reviewed on Oct 4, 2026

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Price was $3,174, price is now $2,635 per person
$2,635
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Augusta (AUG)
No reviews

Sunset Chalet-amazing Views Private hot tub

Sunset Chalet-amazing Views Private hot tub

3 out of 5
Price was $2,248, price is now $1,887 per person
$1,887
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Augusta (AUG)
10/10 Exceptional! (2 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Winslow
View all trips

Stay near popular Winslow attractions

Fort Halifax

9.2/10 (15 reviews)
America's oldest wooden blockhouse stands as a riverside sentinel from the French and Indian War era. Explore this 1754 military relic while enjoying views of the converging Kennebec and Sebasticook rivers.
See properties

Winslow Hotel Deals

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $121 total per night from Nov 19 to Nov 20
$121 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"We loved our room! It was very spacious! Comfortable bed, cozy fireplace, and massage chair! Large TV with full size reclinable couch, coffee table, and the usual fridge, microwave, and Keurig. There was also a safe and ironing board which we didn't need but are helpful to some. Two luggage stands ..."

Reviewed on Nov 1, 2026

Fireside Inn & Suites Waterville
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
$129 nightly
The price is $140 total per night from Nov 29 to Nov 30
$140 total
Nov 29 - Nov 30
Total with taxes and fees
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
$101 nightly
The price is $111 total per night from Nov 8 to Nov 9
$111 total
Nov 8 - Nov 9
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"The neighborhood did not feel secure but the room was nice. Pool is also available for public use, not just hotel guests"

Reviewed on Oct 31, 2026

Senator Inn & Spa
See all 458 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winslow vacation package cost?
Offering great value package deals from $563 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.

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.