Search Deals onWestover Vacation Packages
Westover Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Chestertown
Price was $308, price is now $291 per person
$291
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.

Beach Walk
Price was $2,701, price is now $2,352 per person
$2,352
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.
Reviewed on Oct 13, 2026

Hyatt Regency Chesapeake Bay
Price was $909, price is now $823 per person
$823
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Salisbury (SBY)
Book a stay at this 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.

Studio 6 Suites Pocomoke City, MD
Price was $785, price is now $717 per person
$717
per person
Dec 12 - Dec 19
found 11 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.
Very nice staff. They are working hard to make it better. I definity would stay again.
Reviewed on Oct 29, 2026

Wingate by Wyndham Salisbury MD Airport North
Price was $911, price is now $836 per person
$836
per person
Dec 12 - Dec 19
found 11 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 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.
Parking
Reviewed on Nov 10, 2026

Dagsboro Retreat
Price was $1,400, price is now $1,307 per person
$1,307
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this apartment in Dagsboro. Enjoy free WiFi and free parking. Popular attractions Baywood Greens Golf Course and Nanticoke Indian Museum are located nearby.
I loved it
Reviewed on Jul 17, 2026

Comfort Inn & Suites Chestertown
Price was $387, price is now $362 per person
$362
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.
Convenient location, friendly staff, clean
Reviewed on Nov 8, 2026

Home2 Suites By Hilton Salisbury Fruitland
Price was $770, price is now $767 per person
$767
per person
Jan 15 - Jan 19
found 1 hour ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Salisbury (SBY)
Stay at this hotel in Fruitland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions SU Indoor Tennis Center and Pemberton Historical Park are located nearby.
Westover Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Westover Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Feb 9 - Wed, Feb 24
LGA
LaGuardia
SBY
Salisbury - Ocean City Wicomico Regional
$527 Roundtrip, found 5 days ago
$527
Roundtrip
found 5 days ago

Wed, Feb 17 - Wed, Feb 24
EWR
Newark Liberty Intl. Airport
SBY
Salisbury - Ocean City Wicomico Regional
$549 Roundtrip, found 13 hours ago
$549
Roundtrip
found 13 hours ago

Fri, Jan 8 - Wed, Jan 20
SWF
Stewart Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$623 Roundtrip, found 1 day ago
$623
Roundtrip
found 1 day ago

Fri, Nov 13 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$643 Roundtrip, found 4 days ago
$643
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Chesapeake Bay Vacations
- Salisbury University Vacations
- Chincoteague National Wildlife Refuge Vacations
- University of Maryland Eastern Shore Vacations
- Wicomico Youth and Civic Center Vacations
- Delmarva Discovery Center Vacations
- Smith Island Vacations
- Assateague Lighthouse Vacations
- Wallops Flight Facility Vacations
- Henry S. Parker Athletic Complex Vacations
- Salisbury Zoo Vacations
- Centre at Salisbury Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations


