Shepherd Island

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

The McKernan Inn

3 out of 5
Price was S$2,616, price is now S$2,122 per person
S$2,122
per person
1 Dec - 8 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Portland (PWM)
9.2/10 Wonderful! (60 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland

Reviewed on 18 Aug, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was S$2,801, price is now S$2,304 per person
S$2,304
per person
1 Dec - 8 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Portland (PWM)
9.8/10 Exceptional! (79 reviews)
The property was extreme clean. Staff was extremely helpful and responded quickly to requests. Very safe location. Loved that there was a washer and dryer and also a small kitchen area in the property.

Reviewed on 15 Sept, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was S$3,146, price is now S$2,640 per person
S$2,640
per person
1 Dec - 8 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Portland (PWM)
9.4/10 Exceptional! (280 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on 10 Sept, 2025

Popular places to visit

Wilson Lake

Wilson Lake

Commune with nature and explore the great outdoors at Wilson Lake during your travels in Acton.

Wilson Lake

Hidden Lake

Commune with nature and explore the great outdoors at Hidden Lake during your travels in West Newfield.

Hidden Lake

Lake Ivanhoe Beach

Why not spend a lazy afternoon at Lake Ivanhoe Beach during your trip to East Wakefield?

Lake Ivanhoe Beach

Lake Ivanhoe

Commune with nature and explore the great outdoors at Lake Ivanhoe during your travels in East Wakefield.

Lake Ivanhoe

BLPOA Beach

Why not spend a lazy afternoon at BLPOA Beach during your trip to East Wakefield?

BLPOA Beach

Hansen Pond Preserve

You can take time to visit Hansen Pond Preserve during your travels to Acton.

Hansen Pond Preserve

Top Shepherd Island Hotel Deals

The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd, Laconia, NH
The Naswa Resort
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
352 North St, Saco, ME
Ramada by Wyndham Saco/Old Orchard Beach Area
Weirs Beach Motel and Cottages

Weirs Beach Motel and Cottages

2 out of 5
396 Lakeside Ave, Laconia, NH
Weirs Beach Motel and Cottages
Port Inn & Suites Kennebunk, an Ascend Collection Hotel

Port Inn & Suites Kennebunk, an Ascend Collection Hotel

2.5 out of 5
55 York St, Kennebunk, ME
Port Inn & Suites Kennebunk, an Ascend Collection Hotel
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy, Meredith, NH
Mill Falls Resort Collection at the Lake
Classic Inn

Classic Inn

2 out of 5
21 Ocean Park Rd, Saco, ME
Classic Inn
See all 5,383 properties in Shepherd Island
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.