Raymond Vacations from $824

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Your Raymond Vacation

Book a custom vacation package to Raymond and get ready for your next great adventure. Stay in the neighborhood of North Sebago, which is great for views and camping, for a real taste of this exciting city. If your trip to Raymond includes a little sightseeing, hit up major attractions such as Sebago Lake, Little Sebago Lake and St Josephs College. Stop dreaming and start traveling. Explore the wide range of options on Expedia today and finally put your Raymond vacation plans in motion!

The Latest Raymond vacation packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
Save 100% on your flight
$824
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (65 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
Save 100% on your flight
$847
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

Cliff House Maine

Cliff House Maine

Bald Head
Save 100% on your flight
$1,166
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
$870
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,845 reviews)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

West End
Save 100% on your flight
$1,730
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Staying at the Blind Tiger truly enhanced our experience in Portland. The hotel is thoughtfully planned with tasteful common areas. The rooms were chic and I loved the fireplace in our room.

Reviewed on Oct 3, 2026

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Stay near popular Raymond attractions

Crescent Lake

Crescent Lake's crystal-clear waters stretch across 703 acres of Maine's scenic landscape. Paddle through the Tenney River connection to Panther Pond or cast a line for brook trout in this peaceful outdoor haven.
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Panther Pond

This 1,417-acre Maine lake offers crystal-clear waters perfect for both cold and warm water fishing. Rent a kayak to explore its tranquil shoreline or book a waterfront cottage for an extended summer retreat.
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Rattlesnake Mountain Trail

8.0/10 (3 reviews)
This moderate Maine trail rewards hikers with breathtaking panoramas of Sebago Lake and the Lakes Region. Traverse pine forests to reach multiple viewpoints where the landscape unfolds in spectacular fashion.
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Raymond Pond

Raymond Pond offers crystal-clear waters perfect for fishing, swimming, and kayaking in Maine's natural landscape. Early mornings reveal wildlife and mirror-like reflections across this serene freshwater gem.
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Raymond Cape

This tranquil peninsula extends into Sebago Lake, offering pristine waterfront views and natural Maine beauty. Rent a lakeside cottage for private swimming and spectacular sunset reflections across the clear waters.
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Ramond Beach

This sandy shoreline on Sebago Lake's Jordan Bay offers clear waters perfect for swimming and boating. Enjoy a tranquil day with free parking and easy access for families seeking a refreshing lake experience.
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Raymond Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$71 nightly
$78 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

157 High St Portland ME
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"Quick check-in and check-out. Reasonable valet pricing. ."

Reviewed on Oct 5, 2026

The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$87 nightly
$96 total
Oct 29 - Oct 30
Total with taxes and fees
Fireside Inn & Suites Portland
See all 2,876 properties in Raymond
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 Raymond Vacation Packages

Raymond Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
4,600
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Sebago Lake State Park, Seacoast Adventure and Maine Wildlife Park

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Frequently asked questions

How much does a Raymond vacation package cost?
You can snap up a vacation package to this destination from $824 on Expedia. But how much your vacation to Raymond costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Raymond?
If you'd like to snag a cheap Raymond vacation package, consider traveling in November, December and January. You're likely to find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Raymond?
When planning your Raymond vacation, a few days will be enough to see the best spots. Make sure to stop by Crescent Lake — it's one of the most popular sights in this destination. If you want more adventure, think about basing yourself here and heading off on some day tours from Raymond.
Is it worth booking a vacation package to Raymond?
It's easy to see why a Raymond vacation is on the must-do list of many travelers. Leading attractions like Panther Pond are just the start of things to see and do here.
How to find the best Raymond package deals?
Start your search for a Raymond package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Raymond package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Raymond adventure off to a flying start.
Is it cheaper to book a Raymond vacation as a package?
You can enjoy significant savings on your Raymond escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Raymond?
If you have your Raymond travel dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Raymond?
  1. Pick your dates: What you want to do in Raymond and your favorite season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and flights. Your hotel will probably be the biggest expense during your trip to Raymond.
  3. Use Expedia's trip planning tool to explore Raymond: Research every aspect of your trip to Raymond with this comprehensive planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Determine how many days away: Start by listing all the attractions and activities you'd like to experience in Raymond. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Raymond vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to do and see. Explore some of the incredible things to do in Raymond and book your tickets early to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Raymond vacation packages?
Set off on your dream trip to Raymond with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until the next payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snag great deals while they last.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.