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Smith Island Vacation Packages

Smith Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was $644, price is now $606 per person
$606
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,057, price is now $911 per person
$911
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $826, price is now $761 per person
$761
per person
Dec 11 - Dec 15
found 12 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Price was $792, price is now $730 per person
$730
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Best Western Salisbury Plaza

Best Western Salisbury Plaza

2.5 out of 5
Price was $712, price is now $666 per person
$666
per person
Dec 31 - Jan 4
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Poplar Hill Mansion and Coco's Funhouse are located nearby.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $655, price is now $615 per person
$615
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this motel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $873, price is now $822 per person
$822
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
Wingate by Wyndham Salisbury

Wingate by Wyndham Salisbury

2.5 out of 5
Price was $756, price is now $719 per person
$719
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eastern Shore Baseball Hall of Fame Museum and Arthur W. Perdue Stadium are located nearby.
Gillis Grier Bed & Breakfast

Gillis Grier Bed & Breakfast

3 out of 5
Price was $813, price is now $776 per person
$776
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star B&B in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Poplar Hill Mansion and City Park Picnic Island are located nearby.
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
Price was $765, price is now $732 per person
$732
per person
Dec 31 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Queenstown Harbor Golf Club are located nearby.
Residence Inn by Marriott Salisbury

Residence Inn by Marriott Salisbury

3 out of 5
Price was $951, price is now $911 per person
$911
per person
Dec 11 - Dec 15
found 19 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Salisbury. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

4 out of 5
Price was $853, price is now $819 per person
$819
per person
Dec 11 - Dec 15
found 19 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 4-star beach hotel in Ocean City. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

3-4 Night Vacations in Smith Island

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $770, price is now $718 per person
$718
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,057, price is now $911 per person
$911
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $826, price is now $761 per person
$761
per person
Dec 11 - Dec 15
found 12 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3 out of 5
Midtown Ocean City
Price was $792, price is now $730 per person
$730
per person
Dec 31 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)

5-7 Night Vacations in Smith Island

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

Park Place Hotel

3 out of 5
Downtown Ocean City
Price was $371, price is now $353 per person
$353
per person
Dec 23 - Dec 28
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $492, price is now $416 per person
$416
per person
Dec 23 - Dec 28
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)

Smith Island Last Minute Hotel Deals

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr, Crisfield, MD
Stay at this motel in Crisfield. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Somers Cove Marina and J. Millard Tawes Museum are located ...
Rodeway Inn at Somers Cove Marina
Econo Lodge Princess Anne

Econo Lodge Princess Anne

2 out of 5
10936 Market Lane US 13, Princess Anne, MD
Book a stay at this business-friendly motel in Princess Anne. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Econo Lodge Princess Anne
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

2.5 out of 5
125 Newtowne Blvd, Pocomoke City, MD
Book a stay at this business-friendly hotel in Pocomoke City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Best Western Plus Pocomoke City
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd, Ridge, MD
Stay at this 5-star luxury B&B in Ridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Saint Jerome Beach and Cardinal Gibbons Park ...
Swanendele Inn at St. Mary's Maryland
Onley Inn

Onley Inn

2 out of 5
25297 Lankford Hwy, Onley, VA
Stay at this hotel in Onley. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Onley Inn
Econo Lodge Pocomoke City Hwy 13

Econo Lodge Pocomoke City Hwy 13

2 out of 5
825 Ocean Hwy, Pocomoke City, MD
Book a stay at this business-friendly hotel in Pocomoke City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Econo Lodge Pocomoke City Hwy 13
Best Western Kilmarnock Hotel

Best Western Kilmarnock Hotel

2.5 out of 5
599 N Main St, Kilmarnock, VA
Book a stay at this business-friendly hotel in Kilmarnock. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Kilmarnock Hotel
The Charlotte Hotel & Restaurant

The Charlotte Hotel & Restaurant

3.5 out of 5
7 North Street, Onancock, VA
Stay at this 3.5-star hotel in Onancock. Enjoy free parking, breakfast (surcharge), and daily housekeeping. Popular attractions North Street Market and Red Queen ...
The Charlotte Hotel & Restaurant
See all 449 properties in Smith 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.