Exclusive Sleepers Island Vacation Deals

Sleepers Island vacation package deals

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $559, price is now $415 per person
$415
per person
Mar 16 - Mar 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $651, price is now $507 per person
$507
per person
Mar 16 - Mar 19
found 10 hours ago
Roundtrip 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 – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $609, price is now $479 per person
$479
per person
Mar 16 - Mar 19
found 10 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 is provided and the front desk is staffed around-the-clock.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $710, price is now $584 per person
$584
per person
Mar 16 - Mar 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $672, price is now $562 per person
$562
per person
Mar 16 - Mar 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $544, price is now $456 per person
$456
per person
Mar 16 - Mar 19
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
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.

Frequently asked questions

How much are vacation packages to Sleepers Island?
If you love the sound of hassle-free planning and big savings, our $415 Sleepers Island vacation package has got you covered. With your hotel and flights sorted, organizing your trip around this renowned attraction has never been more simple.
Where can I get the best vacation package deals for Sleepers Island?
Travelocity is the only place you need to go to score an amazing Sleepers Island package deal. Take your pick of 400 airlines and 1,000,000 properties all over the world and craft a travel itinerary that suits your style. With so many options, it's easy to organize your next big escape.
Why should I book my Sleepers Island vacation package via Travelocity?
Whether you're in search of the ultimate unplugged getaway or you crave the fun and excitement of the big city, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available for you round-the-clock.

Top Sleepers Island hotel deals

Sleeper Island need boat dream cabin adventure lakefront family and pet friendly

Sleeper Island need boat dream cabin adventure lakefront family and pet friendly

Alton NH
This cabin featured laundry facilities and barbecue grills.
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Charming 3 story retreat in the shadows of Lake Winnipesaukee

Charming 3 story retreat in the shadows of Lake Winnipesaukee

Alton NH
This chalet features a garden, laundry facilities, and barbecue grills.
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Smith's Point Retreat on Lake Winnipesaukee with indoor pool!

Smith's Point Retreat on Lake Winnipesaukee with indoor pool!

Alton Bay NH
A water park and an indoor pool are featured at this smoke-free vacation home. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Pool
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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.