Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Skowhegan By Kasa

The Skowhegan By Kasa

2 out of 5
per person
Sep 5 - Sep 7
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Augusta (AUG)
A 24-hour gym, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
House near Acadia National Park

House near Acadia National Park

4 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Augusta (AUG)
Topside Inn

Topside Inn

3 out of 5
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Augusta (AUG)
A bar/lounge and a snack bar/deli are featured at this hotel, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. Luggage storage and concierge services are also provided.
Jordan Hotel

Jordan Hotel

3 out of 5
per person
Sep 5 - Sep 7
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Augusta (AUG)
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. 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 and a free area shuttle.

Top Windsor hotels deals

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Free Cancellation
Reserve now, pay when you stay
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This hotel features an outdoor pool and a 24-hour gym. 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
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
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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.
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
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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.
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave, Augusta, ME
Free Cancellation
Reserve now, pay when you stay
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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.
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Free Cancellation
Reserve now, pay when you stay
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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.
Breakfast included
Pet friendly
Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

2.5 out of 5
110 Community Drive, Augusta, ME
Free Cancellation
Reserve now, pay when you stay
Get rates
A restaurant and a gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, express check-out, and dry cleaning are also on offer.
Breakfast included
Pet friendly
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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.

Frequently asked questions

How much are vacation packages to Windsor?
Prepare to be surprised — you can recharge your batteries in Windsor for as low as $317. Let Travelocity save you money and hassle with our vacation packages. With experiences, hotels and flights all in one place, why wait?
Where can I get the best vacation package deals for Windsor?
Travelocity is where to go to score an awesome Windsor package deal. Choose from as many as 400 airlines and 1,000,000 properties around the world and create a vacation package that’s perfect for you. With this amount of choice, now’s the time to book your next big adventure.
Why should I purchase my Windsor vacation bundle with Travelocity?
From incredible destinations to memorable experiences, we have everything you need to satisfy your travel desires. Our 24/7 customer support will also ensure you’re being well taken care of before, during and after your getaway. And don’t panic if you spot a lower price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Will I save money on my Windsor car rental if I combine it with my hotel or flight?
With a Windsor vacation package, you can combine your hotel, car and flight bookings and save a nice amount. If you can’t wait to explore the best of this wonderful destination, why not make tracks to Franconia Notch State Park? This famous attraction is 110 mi from Windsor. With your own wheels, you’ll be there soon enough.
Which airport is best for Windsor?
Portland Intl. Jetport Airport (PWM) is 60 mi from the city center and is the starting point for many adventures. Alternatively, Bangor Intl. Airport (BGR) is 50 mi away from central Windsor and Knox County Regional Airport (RKD) is 30 mi away from central Windsor.
Where should I stay when visiting Windsor?
If you’re searching for somewhere to base yourself, take a look at the Windsor Lakefront House. It’s the top choice for many visitors.

Photos of local treasures

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