The Best Pet-friendly Hotels in Highland, NY from ￥14,935 in 2026

panoramic view of mid hudson bridge over hudson river valley (poughkeepsie, upstate new york) sunny day train station wide angle sun glare crossing suspension small town travel metro north

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Our top choices for Highland pet-friendly hotels

Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (with Sofabed) | Desk, laptop workspace, blackout drapes, soundproofing

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Highland

Leonor

￥14,935 total

includes taxes & fees

Jun 28 - Jun 29

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland

Pinal

￥118,744 total

includes taxes & fees

Jun 9 - Jun 10

Borland House Inn

Montgomery

"Did you ever want to experience what it would be like to stay at a bed in breakfast? Well this is the place to go! So quaint and cute! Located right in the heart of the town of Montgomery. Plenty of things to walk to and see in the area. Brianna the manager was wonderful. Very helpful and informative. The breakfast choices were delicious. Would definitely stay here again and recommend it to others."

roxanne

￥19,101 total

includes taxes & fees

Jun 7 - Jun 8

Breakfast, lunch, dinner and brunch served

Stonehill's Farmhouse

Accord

etgar

￥27,903 total

includes taxes & fees

Jun 9 - Jun 10

Best Western Plus The Inn & Suites At The Falls

Red Oaks Mill

Michele

￥17,233 total

includes taxes & fees

Jun 10 - Jun 11

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Dover Plains

JoAnna S.

￥21,379 total

includes taxes & fees

Jun 8 - Jun 9

Rhinebeck Village Inn

Rhinebeck Village

Nuala

￥21,110 total

includes taxes & fees

Jun 17 - Jun 18

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

New Windsor

Janice

￥17,754 total

includes taxes & fees

Jun 21 - Jun 22

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Top Highland Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

6/10 Okay

"No microwaves in rooms"

DoubleTree by Hilton Poughkeepsie Convention Center

4/10 Poor

"My family and I went on a trip to the Poughkeepsie area due to my son being recruited for football. We arrived at the hotel. The staff was OK. We got up to the room. The room was extremely hot. We made several attempts to call to ask them what was going on they said their air-conditioning was down however it was being fixed now. Mine knew it is easy degrees outside and to me that was an unacceptable response. We waited several more hours. Nothing happened. Had a hard time sleeping went downstairs spoke to the ninth desk clerk. He told me to take the panel off and to turn a button which I was not going to do. This trip was very stressful, and I would never revisit this hotel again in life."

Best Western Plus Kingston Hotel And Conference Center

4/10 Poor

"First Lady at the desk was rude and dismissive from the start and straight up walked away without saying anything. This then turned into a 25-30 minute wait with nobody at the front desk to assist. When the lady eventually came back, she had an even crappier attitude. The second guy (Kevin) was a not much better…. After a two hour and half hour delay to get our room, the lock was busted and when we told him about it he suggested we just use the arm bar on the door (the one that allows partial opening) and thought this was a sufficient answer to the inadequate maintenance they had conducted on their property. It was readily apparent that other room doors had similar problems and damage was plainly visible on many of them from the outside. Kevin’s suggestion was dismissive of the issue at hand, and totally negligent in terms of high quality customer service. All this to say that a quick call to Best Westerns Customer Service support line seemed to motivate the team to finally solve the problems we alerted them to. After another delay, we were provided with a different room that was adequate but smelled strongly of cigar smoke. Overall 1/10 at best. The bed was quality though, I slept soundly."

Frequently asked questions

What's the best pet-friendly hotel in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie is a top dog-friendly hotel, and offers laundry facilities along with WiFi for its human guests.

What's the best time of year to travel to Highland with my pet?

When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Highland are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.

What is there to see and do with your pet in Highland?

Known for its hiking trails, Highland has lots to offer visitors including its riverfront, natural beauty, and mountains. See the local sights and visit Walkway Over the Hudson State Historic Park and Franklin D Roosevelt Library & Museum. While you're there, make sure you don't miss Berean Park Beach and Franny Reese State Park.

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Check availability on Highland Pet-friendly Hotels

Our top choices for Highland pet-friendly hotels

SureStay Plus Hotel by Best Western Highland Poughkeepsie