Assateague Island Pet-friendly Vacations

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Flight and Pet-friendly hotel deals in Assateague Island

Price found within the past 48 hours. Click for updated prices.
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

Midtown Ocean City
CA $1,586
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (1,358 reviews)
We love staying here because of the views and large rooms with tub. However this week, they had a temporary water shutoff and didn’t tell us until 45 mins after they shut it off. My husband was in the shower and was covered in soap when he found out. We called the front desk to be told “oh yeah it’ll be off for a couple hours. a flyer is to be posted on your door” (it wasn’t until an hour later and the damage already done) This is a nice hotel and not cheap. Getting a heads up that our water was going to be shutoff would’ve been at minimum the right thing to do. Especially for rooms that have kitchens and tubs! Then there’s the parking….hidden fee of $10 a day to park on premises. No other options. Just include it in the total ahead of time instead of offering the surprise, especially when there are no other options. It’s bare miminum customer service 101! (Or should be)

Reviewed on Oct 14, 2026

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

CA $1,787
per person
Dec 23 - Dec 30
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
8.8/10 Excellent! (1,009 reviews)
Cypress River Inn & Spa

Cypress River Inn & Spa

CA $2,242
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very good! (7 reviews)
The bathroom vent had mold. I have photos of the vent

Reviewed on Sep 25, 2026

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5* Pet-friendly holidays in Assateague Island

Price found within the past 48 hours. Click for updated prices.
Cypress River Inn & Spa

Cypress River Inn & Spa

CA $2,242
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very good! (7 reviews)
The bathroom vent had mold. I have photos of the vent

Reviewed on Sep 25, 2026

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4 Night Pet-friendly holidays in Assateague Island

Price found within the past 48 hours. Click for updated prices.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

CA $1,200
per person
Dec 10 - Dec 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9.4/10 Exceptional! (858 reviews)
Beach Walk

Beach Walk

Downtown Ocean City
CA $3,309
per person
Dec 10 - Dec 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

North Ocean City
CA $1,276
per person
Dec 10 - Dec 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (2,809 reviews)
The pool is spectacular. This was a main reason my family selected this hotel. Another reason was the availability of a few on site restaurants. Unfortunately, presumably due to it being offseason, two of the three restaurants were not open as advertised. I understand that restaurant hours might need to change, but it would have been helpful for the hotel to have provided updated information about this upon check in so my family could make alternate arrangements instead of trying to figure out what/when restaurants in the hotel would be open on our own on a daily basis. Signage indicating restaurant hours that was posted outside restaurant was inaccurate as well. Aside from this inconvenience, we would stay here again.

Reviewed on Oct 15, 2026

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Things to do

Ocean City: Ripley's Believe It or Not! + Mirror Maze

Ocean City: Ripley's Believe It or Not! + Mirror Maze

CA $39
per adult
Ocean City: Ripley's Believe It or Not! + Mirror Maze
Ocean City: Downtown and Boardwalk Foodie Walking Tour

Ocean City: Downtown and Boardwalk Foodie Walking Tour

CA $154
per adult
100% of travellers recommend
Ocean City: Downtown and Boardwalk Foodie Walking Tour
Berlin, Maryland: Historic Walking Food Tour with Tastings

Berlin, Maryland: Historic Walking Food Tour with Tastings

CA $154
per adult
Berlin, Maryland: Historic Walking Food Tour with Tastings
See all activities in Assateague Island

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