Portsmouth doesn't chase the spotlight the way Nantucket or Kennebunkport do, and that's part of its appeal. Founded in 1623, this compact New Hampshire coastal city packs colonial history, boutique shopping and a genuinely good dining scene into a downtown built around pedestrian-friendly Market Square. With the University of New Hampshire nearby, there's a younger energy here than in most historic New England towns — and a TravelAwaits roundup of seven Vrbo rentals makes the case for exploring it all on foot.
The standout for location is Tugboat Vista, a two-bedroom overlooking the Piscataqua River with views of Memorial Bridge. Tugboats pass right by the windows, which is about as Portsmouth as it gets. Couples after something simpler can book the Historic 1BR in the historic district, which keeps its exposed brick and wood beams but adds a full kitchen — handy, though the city's best restaurants are minutes away anyway.
Design lovers get the Penthouse at Penhallow, a two-bedroom with exposed brick, beams and leather furniture in the heart of the historic area. Two flights of stairs and no elevator is the trade-off. History buffs should look at the Sunny Private Studio, part of the former home of Daniel Webster, the two-time Secretary of State; it's basic (kitchenette, non-working fireplace) but comes with a parking spot.
Groups have options too. Historic Charm in West End is a four-bedroom home on land first settled in 1623, with the current house dating to 1869, plus gardens that have made a local tour and a backyard fire pit. The State Street Parlor, a freshly updated two-bedroom just outside the downtown core, is the budget pick — bold wallpaper, a sunroom porch, a fenced yard and pet-friendly policies. And Downtown House sleeps up to ten across three king bedrooms and sofa beds, best suited to a group of six who want real beds and a big open kitchen-living space.
Why it matters: Portsmouth is an easy fall trip for travellers who want walkability over driving, history over theme parks, and a rental that puts dinner and drinks within a ten-minute stroll. Autumn brings crisp weather, fewer crowds than the Cape, and fire-pit evenings — exactly what most of these listings are set up for.
