Oscar’s Travels – Our Pet Friendly Stay at The Wolfeboro Inn

gazebo at the pet friendly Wolfeboro Inn
The Gazebo


Leaving your pet behind when you vacation is never easy. My situation with Oscar got more complicated last year when he was diagnosed with diabetes. Now, he requires two insulin shots a day and while he is doing very well, I worry about him much more than before. So whenever possible, I like to travel with him.

We’ve rented a house with him before and that was pretty seamless. This past weekend, however, we decided to try something new and checked into a pet friendly hotel. On a whim, I called The Wolfeboro Inn on Lake Winnipesaukee and, by chance, they had a pet friendly suite available for just one night. We took it! The ground level room was very spacious and its patio door led us right out to the property’s grassy lawn. It was perfect.


my daughters and dog on the dock at the Wolfeboro Inn
A walk on the Inn’s dock


Oscar was certainly nervous and excited. He’s a Schnauzer; by nature he’s rigid with his schedule and routine. I knew it would take him time to adjust to this new situation. I made no plans to rush out for the first few hours and planned nothing where he couldn’t come along. In the evening, we dined in the hotel’s, Wolfe’s Tavern, so that we could check on him frequently. He never made a peep.

During the day, he joined us for lunch, a little shopping, a lot of walking and, for the first time since we’ve had him, swimming. We adopted Oscar when he was seven in 2013 and since then I’ve always wondered if he could swim. What better place to test the waters than the lake. I’m happy to say, he pulled off a doggie paddle like a pro.


oscar's first swim in lake winnipesaukee
He did it!


I really enjoyed this experience with Oscar. It brought a new dimension of fun to our travels and it certainly encouraged conversation. So many nice folks stopped to talk and give Oscar a pat on the head. I’d be lying if I said it wasn’t tiring – for the both of us.


my dog oscar sleeping
Wiped out!


There were so many new things for Oscar to experience and for me to take into consideration that we both crashed on the drive home. The funniest experience was when we walked into the hotel lobby in the morning for coffee and he began barking at all of the people who he seemed to think were invading his space. I imagine his mindset was, “why are all these strangers here in my big new house?” Well, that certainly woke me up.

The best part – no one so much as flinched. The hotel receptionist was obviously accustomed to the pet friendly environment and just smiled while a lovely couple, who were staying at the hotel with their two Maltese, came right over to say hi and calm Oscar’s nerves.

I think, for Oscar, a few more five-star stays would be just what he needs to get more comfortable. I would love to try the grand Wentworth by the Sea in New Castle, NH and The Woodstock Inn in Vermont – both of which offer pet accommodations.

Do you travel with your dog? Any suggestions or recommendations?

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7 years ago

Glad that you and Oscar had fun in your old stomping grounds! Topnotch in Stowe, VT is a wonderful pet-friendly resort. Makes for an awesome fall getaway.

7 years ago

Oscar had a more relaxing vacation than I did!!!!! Good for him.

7 years ago

Glad you had such a good experience, ours, however, wasn’t as smooth. It’s nice to know that there are nice hotels that offer pet friendly accommodations, maybe we’ll give it a try again.