Small Point Vacation Packages for 2025
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Small Point Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites By Wyndham Windham
Save 100% on your flight
per person
Jun 30 - Jul 5
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.
Chebeague Island Inn
Save 100% on your flight
per person
Jun 9 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
per person
Jun 30 - Jul 5
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection
Save 100% on your flight
per person
Jun 19 - Jun 24
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.
Cambria Hotel Portland Downtown-Old Port
East Bayside
Save 100% on your flight
per person
Jun 30 - Jul 5
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The McKernan Inn
Save 100% on your flight
per person
Jun 19 - Jun 24
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
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The Freeport Hotel, Ascend Hotel Collection
506 Us Route 1, Freeport, ME
25.49 km from Small Point
Book a stay at this business-friendly motel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Harraseeket Inn & Event House
162 Main St, Freeport, ME
25.15 km from Small Point
Stay at this 3.5-star business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express Hotel & Suites Freeport by IHG
450 U.S. Route 1, Freeport, ME
25.63 km from Small Point
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Travelers Inn
130 Pleasant St, Brunswick, ME
22.84 km from Small Point
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Residence Inn Bath Brunswick Area
139 Richardson St., Bath, ME
19.12 km from Small Point
Book a stay at this business-friendly hotel in Bath. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the property ...
Comfort Inn Brunswick
199 Pleasant St, Brunswick, ME
23.17 km from Small Point
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
SpringHill Suites by Marriott Freeport Brunswick
500 US-1, Freeport, ME
25.57 km from Small Point
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Fairfield Inn & Suites by Marriott Brunswick Freeport
36 Old Portland Rd, Brunswick, ME
23.69 km from Small Point
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hilton Garden Inn Freeport Downtown
5 Park St, Freeport, ME
24.88 km from Small Point
Stay at this 3-star business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Tugboat Inn
80 Commercial St., Boothbay Harbor, ME
21.12 km from Small Point
Stay at this 3-star hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the helpful staff in our reviews. ...
Flagship Inn and Suites
200 Townsend Avenue, Boothbay Harbor, ME
22.11 km from Small Point
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular ...
Hampton Inn Freeport/Brunswick
194 Lower Main St, Freeport, ME
25.34 km from Small Point
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Casco Bay Inn
107 US Route 1, Freeport, ME
26.2 km from Small Point
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, May 29 - Wed, Jun 4
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Sun, Aug 17 - Tue, Aug 19
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Sat, Jun 28 - Sat, Jul 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227 Roundtrip, found 1 hour ago
$227
Roundtrip
found 1 hour ago
Wed, Sep 3 - Wed, Sep 10
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Best points of interest in Phippsburg
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