The Black Point Inn offers stunning waterfront on three sides, in a secluded spot along Western Cove. It's the only resort on Prouts Neck, and many guest enjoy the remote environment (though it's still convenient, as Portland is only a 20-minute drive away). Spacious rooms have classic New England style, and there are two restaurants on-site (so visitors won't have to drive all the way back into town to get a meal). There's a heated pool , but no spa or Jacuzzi, and the property is open only seasonally.

Miller’s Guest House is a waterfront guest house on Tobago’s Buccoo Point that draws budget travelers and backpackers. It’s eight compact, air-conditioned rooms are worn and include bright, colorful interiors, hardwood furniture, and TVs (some have flat screens). It’s a low-frills kinda place but the ocean-view restaurant serves up tasty Trinidadian and international dishes. There’s no pool and although its located next to the water, the waterfront is used by fishermen and isn’t swimmable -- the swimming beach is a five-minute walk away. The hotel rents snorkeling equipment and beach chairs. For a similar stay also on Buccoo Bay, it’s worth considering the nearby Fish Tobago Guesthouse, which has slightly nicer rooms, lush grounds, and a communal kitchen.