Great Island Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
Top Luxury vacation packages in Great Island
Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview
Downtown Portland
Price was $514, price is now $433 per person
$433
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
8.8/10 Excellent! (1,007 reviews)
Clean and great staff, plenty of places to eat or go out that is very close walking distance to the hotel
Reviewed on Aug 20, 2025
Cliff House Maine
Save 100% on your flight
Price was $1,653, price is now $1,179 per person
$1,179
per person
Sep 30 - Oct 4
found 24 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025
Inn By The Sea
Save 100% on your flight
Price was $877, price is now $645 per person
$645
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025
Kennebunkport Captains Collection
Price was $665, price is now $495 per person
$495
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
9.4/10 Exceptional! (608 reviews)
We stayed in one of the older / darker rooms. It had charm but in hindsight, I would have preferred the brighter rooms which were pictured on the website.
A hot breakfast is included with one hot dish each morning as well as fruits and yogurt. One of our egg dishes was undercooked and the yogurt offered was underwhelming- most likely from store bought containers.
It is a great location, walking distance to all of the restaurants, bars and shopping. We had our car so we were able to drive to other popular sites including the beach.
Reviewed on Aug 18, 2025
Portland Harbor Hotel
Downtown Portland
Price was $577, price is now $436 per person
$436
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Lovely and knowledgeable staff. Welcoming and romantic stay in a foodie and artsy community.
Reviewed on Aug 20, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Island
View all trips5* Luxury vacations in Great Island
Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Resorts Collection
Save 100% on your flight
Price was $4,300, price is now $3,776 per person
$3,776
per person
Sep 30 - Oct 4
found 24 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (100 reviews)
Best resort ever! I can't say one bad thing about this place. Loved loved loved the room they gave us! Super huge and spacious! amazing bathroom, all impeccably decorated and a most comfortable bed. the pool area is gorgeous and relaxing. the restaurant totally spectacular. they had Mercedes - like 5 of them of all types, including a Mayback that they just lend out to their guests for 4 hours at a time. They also have bikes and the town is very bicycle friendly. The hotel is perfectly situated between the downtown brimming with restaurants and cafes and the gooches beach that allows dogs during certain hours so our doggie got to swim in the ocean for the very first time in her life. Was brilliant. the whole stay totally memorable. could not recommend this place any more. please go!
Reviewed on Aug 20, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Island
View all trips3 Night Luxury vacations in Great Island
Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection
Price was $665, price is now $495 per person
$495
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
9.4/10 Exceptional! (608 reviews)
We stayed in one of the older / darker rooms. It had charm but in hindsight, I would have preferred the brighter rooms which were pictured on the website.
A hot breakfast is included with one hot dish each morning as well as fruits and yogurt. One of our egg dishes was undercooked and the yogurt offered was underwhelming- most likely from store bought containers.
It is a great location, walking distance to all of the restaurants, bars and shopping. We had our car so we were able to drive to other popular sites including the beach.
Reviewed on Aug 18, 2025
Inn By The Sea
Save 100% on your flight
Price was $877, price is now $645 per person
$645
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025
Cliff House Maine
Save 100% on your flight
Price was $3,500, price is now $2,636 per person
$2,636
per person
Oct 5 - Oct 8
found 20 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Island
View all trips4 Night Luxury vacations in Great Island
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $655, price is now $457 per person
$457
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Lovely and knowledgeable staff. Welcoming and romantic stay in a foodie and artsy community.
Reviewed on Aug 20, 2025
The Docent's Collection
Downtown Portland
Save 100% on your flight
Price was $821, price is now $574 per person
$574
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
This property was beyond expectation. As long as you are comfortable using the app, check in was super easy and so was getting into our suite. The kitchen had everything we could have possibly needed, and having a living space was a great lift from a normal hotel room.
Reviewed on Aug 16, 2025
Inn By The Sea
Save 100% on your flight
Price was $1,020, price is now $720 per person
$720
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Island
View all tripsAll you need to know about luxury vacations in Great Island
What can I expect from a luxury Great Island vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Great Island vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.
How can I find all-inclusive luxury vacation packages in Great Island?
By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.
Can I book a cheap Great Island luxury vacation?
Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $433. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Great Island?
Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.
Can I book a package in Great Island with a luxury vacation home?
A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.
How can I find the best luxury vacation deals in Great Island?
Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.
Can I book a luxury holiday in Great Island with free cancellation and/or flexible dates?
Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.
Why should I book my luxury trip to Great Island with Expedia?
A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.