Little Diamond Island Vacation Deals: Little Diamond Island, Portland Vacations

Little Diamond Island vacation package deals

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

Ramada Plaza by Wyndham Portland

Nasons Corner

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Portland (PWM)

2 hot tubs, an indoor pool, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Cliff House Maine

Save 100% on your flight

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Kennebunkport Captains Collection

Save 100% on your flight

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Portland (PWM)

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

Inn By The Sea

Save 100% on your flight

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

The McKernan Inn

per person

Sep 8 - Sep 11

found 14 hours ago

Roundtrip non-stop flight included

Charlotte (CLT) 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.

Frequently asked questions

How much are vacation packages to Little Diamond Island?

Let Travelocity take all the hard work out of arranging your trip to Little Diamond Island. Take a look at our fabulous $561 package deal and save both time and money. With your flights and hotel locked in, you can channel your energy into planning the fun parts of your adventure — like crossing off those well-known attractions!

Where can I get the best vacation package deals for Little Diamond Island?

With around 400 airlines and 1,000,000 properties around the world, you can't go wrong with Travelocity. Look through our comprehensive range and pick up the best Little Diamond Island package deal. Isn't it amazing when vacation planning is that easy?

Why should I purchase my Little Diamond Island vacation package via Travelocity?

By booking your hotel, flights, car rental and activities all in the one place, you'll save big bucks as well as precious time. All our bookings come with an expert team of customer service specialists available 24/7, and you'll know that you'll always be getting the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book the getaway of your dreams today and get packing!

Top Little Diamond Island hotel deals

Large, light filled 4 bedroom house - walk to ocean and ferry

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Inn On Peaks Island

33 Island Avenue, Peaks Island, ME

$365 nightly

$398 total

Jul 31 - Aug 1

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. Wedding services are provided for your convenience.

Parking included

Free WiFi

Portland Regency Hotel & Spa

20 Milk Street, Portland, ME

$302 nightly

$335 total

Aug 27 - Aug 28

Total includes taxes and fees

A full-service spa, a hot 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.

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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.