Deals on vacations and trips to Chebeague Island

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Chebeague Island flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Jul 3 - Jul 7
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. A bar/lounge, a terrace, and a garden are also provided.
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
Downtown Portland
per person
Jul 3 - Jul 7
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a gym on site, and laundry facilities and concierge services are also offered.
Hidden Pond

Hidden Pond

4 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
A full-service spa, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Families will appreciate the arcade/game room and picnic area. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and a beach shuttle.
White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Enjoy the seasonal outdoor pool and perks like free valet parking.

Top Chebeague Island hotel deals

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $85 per night
$85
per night
Apr 28 - Apr 29
This hotel features 2 restaurants, 2 spa tubs, and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Hot Tub
Pet friendly
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $178 per night
$178
per night
May 6 - May 7
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
Pet friendly
Breakfast available
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $145 per night
$145
per night
Apr 28 - Apr 29
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Pet friendly
Breakfast available
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $80 per night
$80
per night
Apr 28 - Apr 29
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pet friendly
Breakfast included
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $197 per night
$197
per night
May 14 - May 15
This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Breakfast available
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $172 per night
$172
per night
Apr 29 - Apr 30
A full-service spa, a spa tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.
Hot Tub
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 Chebeague Island?
Prepare to be pleasantly surprised — you can unwind in Chebeague Island for only $979. Allow Travelocity to save you time and stress with our vacation packages. With flights, hotels and tours all ready to go, why wait?
Where can I get the best vacation package deals for Chebeague Island?
Check out Travelocity. With access to 400 airlines and a whopping 1,000,000 properties across the globe, finding the perfect Chebeague Island package deal couldn’t be easier.
Why should I purchase my Chebeague Island vacation bundle via Travelocity?
With our Price Match Guarantee, we’ll match any better price you find. Add to that our 24/7 support and high-quality service and the vacation you’ve been dreaming of is closer than ever before.
Will I save money on my Chebeague Island car rental if I combine it with a hotel or flight?
Bundling your bookings into a Chebeague Island vacation package will save you a tidy sum. You can combine a flight and car; a hotel, car and flight; or a hotel and car. You won’t find a better way to explore the greater Chebeague Island area than with your own ride. You can also add experiences and activities to your Travelocity package.
What is the best time of year to go to Chebeague Island?
You’ll land the lowest hotel prices around and pay the highest prices during . You can expect it to be more relaxed in November, December and January, while you’re likely to find more fellow travelers to meet during March, July and August. It comes down to what prices you’re willing to pay, the weather conditions and how you deal with crowds.