Pet-friendly vacation rentals in Westport Island

Tiny A-Frame Romantic Getaway

Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

Pets · Outdoor spaces · Laundry

Maine Cottage/Your Year-Round Destination

The Stowaway sits on 5.5 private acres atop a hill with breathtaking waterviews from every level. This pet-friendly, 3 story home offers 4 bedrooms, 3 baths & sleeps 8. Perfect for family getaways, milestone celebrations or relaxing escapes, the cottage combines comfort & style! The carriage house sleeps 4 more & together the property can host events of 50-150 guests (event fee $9000). Explore Maine's beauty year-round from summer by the sea, to colorful fall foliage, to snowy winter holidays.

Outdoor spaces · Pets · Kitchen

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Walkability · Pets · Check-in

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Outdoor spaces · Pets · Bathroom

Captain Fuller House: Boat Builders Retreat - Main

Wake up to sweeping views of Linekin Bay at this pet-friendly coastal retreat . Nestled in a quiet neighborhood, the home sleeps 6–8 guests with three bedrooms and two full bathrooms, perfect for families or small groups. Enjoy peaceful waterfront scenery, fresh ocean air, and easy access to Boothbay Harbor. Modern comforts include an on-site EV charger, while classic Maine charm makes it an ideal place to relax, recharge, and enjoy life by the bay—paws included.

Pets · Outdoor spaces · Accuracy

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

Outdoor spaces · Walkability · Backyard

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

Pets · Walkability · Long stay

Captains View at Pemaquid Point

Brand New Construction 2021!! Sitting on almost 3 acres on Pemaquid Point with ocean view, beautiful sunsets, pounding surf, white sand beach, tidal pools, and your own cathedral forest to play in , have a picnic or whatever you want- Captains View is part of Cottages at the Point and is the sister cottage to Arch Angel. Rent one or both!

Walkability · Pets · Bathroom

Classic Maine, Modern Comfort

NOTE: Summer Bookings are 7 Days from Saturday-Saturday and tend to fill up by February/March or sooner. All the comforts of home while you're away from home. Come enjoy a newly built beach house (2008) just short walk from beautiful Popham Beach - one of Maine's most beautiful and expansive beaches, one hour north of Portland, Maine.

Pets · Walkability · Amenities

Beautiful Summer River Retreat

Charming victorian house on the Kennebec River on the outskirts of historic and beautiful Bath, Maine. Close to great shops, restaurants, ski slopes and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Maritime Museum and a scenic dog park.

Outdoor spaces · Pets · Location

Sheepscot Harbour Village - 3 Bd Condo Waterview

Relax with the whole family at this peaceful place to stay. This newly renovated and well kept cottage features water views and easy access to all attractions. Located with in Sheepscott Bay Village with Deep Water dock and on site restaurant (seasonal pop-up). You will be in the middle of it all.

Pets · Outdoor spaces · Getting around

Newly renovated 3BR house w/ stunning ocean views

Relax and unwind with family and friends in this newly renovated 3 bedroom, 2 bathroom house at Popham Beach. The house features breathtaking ocean views from every room and is just steps to the 7-mile sandy beach, which is never crowded. The only way to be closer to the ocean is to be in it!

Walkability · Outdoor spaces · Cleanliness