Gray Vacation Packages 2025/2026 from $576

Gray flight + hotel vacation packages

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

The McKernan Inn

$576

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Portland (PWM)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

The Docent's Collection

Downtown Portland

Save 100% on your flight

$900

per person

Oct 25 - Oct 31

found 20 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out and dry cleaning are also provided.

Canopy by Hilton Portland Waterfront

Downtown Portland

Save 100% on your flight

$980

per person

Oct 25 - Oct 31

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

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.

Homewood Suites by Hilton Portland

$691

per person

Oct 25 - Oct 31

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a free grocery shopping service are also on offer.

Hampton Inn & Suites Portland West

Nasons Corner

$690

per person

Oct 25 - Oct 31

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Gray hotels deals

Clarion Hotel Portland

1230 Congress St, Portland, ME

$152 nightly

$168 total

Oct 19 - Oct 20

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

Germaine Inn South Portland

675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME

Free Cancellation

$85 nightly

$93 total

Oct 23 - Oct 24

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

340 Park Ave, Portland, ME

$149 nightly

$165 total

Oct 20 - Oct 21

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$314 nightly

$347 total

Oct 22 - Oct 23

Total with taxes and fees

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

Free WiFi

Portland Harbor Hotel

468 Fore Street, Portland, ME

$348 nightly

$385 total

Oct 20 - Oct 21

Total with taxes and fees

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

Free WiFi

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$136 total

Oct 19 - Oct 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

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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.

Popular places to visit

Maine Wildlife Park

Take the family on an outing to Maine Wildlife Park during your trip to Gray. While you're here, you can savor the top-notch restaurants.

Spring Meadows Golf Course

Enjoy a round of golf in Gray at Spring Meadows Golf Course. While you're in the area, find time to visit its shops.

Frequently asked questions

How much are vacation packages to Gray?

Get ready to be surprised — you can vacation in Gray for a paltry $576. Let Travelocity save you money and hassle with our fantastic vacation packages. With experiences, hotels and flights all ready to go, why put it off?

Where can I get the best vacation package deals for Gray?

Travelocity has everything you need to score a great Gray package deal. Take your pick of 400 partner airlines and 1,000,000 properties around the world and create a vacation package that suits your style. With so much choice, it's easy to organize your next big adventure.

Why should I book my Gray vacation bundle via Travelocity?

Because we believe in crafting unforgettable vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our support team is on hand 24/7 to make sure you'll never roam alone. We also have a Price Match Guarantee, so you can secure your trip knowing you've landed the best deal possible.

Can I save on my Gray car rental if I book it with hotels and flights?

Combining your flight, car and hotel into a Gray vacation package is a surefire way to land the best prices. Plus, having your own rental car gives you freedom to get to all those famous sights you're hoping to explore. Sitting 110 mi away from Gray, Fenway Park is one place that should be on your agenda. Load up the car and make a day trip of it.

Which airport is best for Gray?

Portland Intl. Jetport Airport (PWM) is where many travelers step off the plane. You'll find it located around 17 mi south from inner Gray. You can also check out the deals to Augusta State Airport (AUG), which is 40 mi away from central Gray.

What is there to do in Gray?

Snap up the excellent photo-ops at Spring Meadows Golf Course, one of the most well-known attractions in Gray. There's plenty more to discover in this exciting city, so make sure you have enough time to explore some off-the-beaten-path gems.

Where should I stay when visiting Gray?

If you're searching for someplace comfortable to lay your head, have a look at the [Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger](https://www.travelocity.com/Gray-Hotels-Edgewater-Retreat-On-Little-Sebago-Lake-Lakefront-WSauna-EV-Charger.h101762094.Hotel-Information). It's the top choice for many travelers.