Deals on vacations and trips to Winslow

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Winslow flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was $706, price is now $625 per person
$625
per person
Oct 8 - Oct 12
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Augusta (AUG)
Ski-in/ski-out access, a gym, and a restaurant are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski rentals and ski passes are available on site. Enjoy the outdoor pool and perks like free self parking.
Topside Inn

Topside Inn

3 out of 5
Price was $2,390, price is now $2,057 per person
$2,057
per person
Oct 1 - Oct 5
just found
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
A bar/lounge and a garden are featured at this hotel, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A snack bar/deli, luggage storage, and concierge services are also on offer.
Five Gables Inn

Five Gables Inn

3 out of 5
Price was $937, price is now $833 per person
$833
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.
Peaceful Lakefront Escape With Outdoor Dining, Beach Access, Deck & Firepit

Peaceful Lakefront Escape With Outdoor Dining, Beach Access, Deck & Firepit

2 out of 5
Price was $1,781, price is now $1,606 per person
$1,606
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Augusta (AUG)
This vacation home features laundry facilities. Take advantage of the free self parking.
Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $1,329, price is now $1,209 per person
$1,209
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Fargo (FAR) to Augusta (AUG)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A 24-hour business center, a lobby fireplace, and a communal living room are also on offer.

Top Winslow hotels deals

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $138 total per night
$138 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features a hot tub, a gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Free parking, a business center, and free WiFi in public areas are also offered.
Pool
Hot Tub
Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd Augusta ME
Free Cancellation
$151 nightly
The price is $165 total per night
$165 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave Augusta ME
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $149 total per night
$149 total
Sep 30 - Oct 1
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr Waterville ME
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $138 total per night
$138 total
Sep 22 - Sep 23
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Days Inn by Wyndham Augusta

Days Inn by Wyndham Augusta

2 out of 5
18 Edison Dr. Augusta ME
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $119 total per night
$119 total
Aug 31 - Sep 1
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden and a computer station are also provided.
Breakfast included
Pet friendly
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St Waterville ME
Free Cancellation
$119 nightly
The price is $130 total per night
$130 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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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.

Stay near popular Winslow attractions

Fort Halifax

9.2/10 (15 reviews)
Learn about the local history of Winslow when you spend time at Fort Halifax. Stroll along the riverfront or experience the area's entertainment venues.
See properties

Frequently asked questions

How much are vacation packages to Winslow?
Starting from as little as $625, flight and hotel packages are a superb way to stretch your vacation budget. Winslow, here you come!
Where can I get the best vacation package deals for Winslow?
With around 400 air carriers and 1,000,000 properties across the globe, you can't go wrong with Travelocity. Browse our comprehensive range and pick up the best package deal to Winslow. Isn't it great when organizing a trip is that easy?
Why should I book my Winslow vacation bundle with Travelocity?
You'll not only enjoy huge savings, but you'll also have access to our round-the-clock support, top-notch service and a Price Match Guarantee. Roam across the globe, uncover hidden gems and create lifelong memories — we'll take care of the important details.
Will I save money on my Winslow car rental if I bundle it with hotels and flights?
Absolutely — and if you also add an activity or experience to your Winslow vacation package, you'll save even more. With a package, you can find things to do in the area that are perfect for you, Then, jump in your rental car and work your way through the list. Franconia Notch State Park is one terrific attraction to visit. It's 110 mi from Winslow.

Photos of local treasures

Browse Winslow vacation photos for more inspiration

A steel bridge over a river with lush greenery on both sides.
A suspension bridge with a red structure on the right side, a river below, and trees in the background.
A steel bridge with a truss design, surrounded by lush green trees and a body of water.
A rocky shoreline with a lake, autumn leaves, and a cloudy sky.