Caine Woods Vacations from $518

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Your Caine Woods Vacation

Our Caine Woods vacation packages are a fast and practical way to plan and reserve your next getaway. Experience the magic of this unique neighborhood without the hassle of organizing it all yourself. Not sure what to do and see during your trip to Caine Woods? Nearby attractions such as Maryland Beach, Carousel Ice Skating Rink and Northside Park are excellent places to start. Whatever your travel goals or the size of your budget, booking the ultimate Caine Woods vacation has never been easier with Expedia.

The Latest Caine Woods Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $637, price is now $518 per person
$518
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
17.6/10 Exceptional! (1,002 reviews)
Clean room, convenient on-site parking. Just be aware that if your room faces Dickinson Ave, the LED sign for the Nalu Grill will be blasting a rainbow of light into your window all night long if you don’t position the blackout curtains perfectly w/ zero gaps.

Reviewed on Nov 19, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,550, price is now $1,753 per person
$1,753
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
15.2/10 Exceptional! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

2.5 out of 5
Downtown Ocean City
Price was $1,129, price is now $939 per person
$939
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
18.4/10 Exceptional! (1,112 reviews)
Not much to do during off season here. Since, it's a Howard Johnson's you would expect a Howard Johnson restaurant to be there right? Nope. I'm sure during the summer the place is hoping. Other good places around to eat thankfully. Not bad place.

Reviewed on Nov 22, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $773, price is now $648 per person
$648
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
16.8/10 Exceptional! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Price was $743, price is now $629 per person
$629
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Salisbury (SBY)
17.2/10 Exceptional! (58 reviews)
Did not like the outdated furniture, small televisions and the hot tub wasn’t sanitized until the next day. Notified office told them hot tub cover was not on and they said they were waiting for a new cover to come in. Pools don’t open until 10 There were ants on the counter tops and the first night we were locked out . Staff said they had us listed as checked out . We did get new cards immediately. We have stayed in the condos for over 30 years Disappointed especially for paying g what we paid

Reviewed on Jul 7, 2025

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Where to stay in Caine Woods

Find the best Caine Woods areas and neighborhoods for the activities you enjoy most. Learn more about Caine Woods
North Ocean City featuring swimming, a beach and general coastal views

North Ocean City

3 out of top 10 points of interest in this area

A pretty shoreline, miniature golf, watersports and seafront accommodations make this a great spot for a fun-filled summer vacation.

Find hotels in North Ocean City

Caine Woods Hotel Deals

Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Dec 8 to Dec 9
$84 total
Dec 8 - Dec 9
Total with taxes and fees
8.6/10 Excellent! (1,995 reviews)
The room was very clean and the staff was friendly and helpful.

Reviewed on Nov 18, 2025

Fenwick Inn
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
1 16th Street Ocean City MD
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Nov 30 to Dec 1
$89 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,586 reviews)
A nice spot with great views of the beach and boardwalk. A touch dated, the tech is behind by about 4 years, so no USB-C ports or streaming apps. But you’ll be too busy sleeping or out and about to notice. Good location near a lot of restaurants within walking distance but about a 30 minute walk ...

Reviewed on Nov 19, 2025

Hyatt Place Ocean City / Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
$88 nightly
The price is $97 total per night from Nov 25 to Nov 26
$97 total
Nov 25 - Nov 26
Total with taxes and fees
8.6/10 Excellent! (2,273 reviews)
Staff was great

Reviewed on Nov 17, 2025

Princess Royale Oceanfront Resort
See all 11,799 properties in Caine Woods
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Caine Woods

Ocean City Boardwalk featuring rides

Ocean City Boardwalk

4.5/5(1,896 reviews)

Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.

Ocean City Boardwalk
Ocean City Beach which includes rides and a sandy beach as well as a small group of people

Ocean City Beach

4.5/5(1,615 reviews)

Swim in the waves of the Atlantic Ocean, relax on soft white sands or stroll by the arcades and shops on the exciting boardwalk at this family-friendly city beach.

Ocean City Beach
Roland E. Powell Convention Center which includes general coastal views

Roland E. Powell Convention Center

4/5(285 reviews)

You can always find something exciting to see or do at this entertainment complex in the heart of Ocean City, with major music concerts and events.

Roland E. Powell Convention Center

Things to do

Bethany Beach Bash Scavenger Hunt

Bethany Beach Blitz Scavenger Hunt

$29
per adult
Bethany Beach Blitz Scavenger Hunt
Historic Berlin Foodie Tour

Berlin Tasting Tour: A Delicious Walk Through History

$110
per adult
Berlin Tasting Tour: A Delicious Walk Through History
See all activities in Ocean City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.