Winter Harbor Classified Ad Listings

Avg / night: $863. Enchanting dog-friendly ocean view home with grill, balcony, TV, & deck | Located in Southwest Harbor, ME | 4.43 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Listen to wildlife sing at The Birdhouse of Maine! You'll be just a short drive away from the wonderful Arcadia National Park, where you'll be able to hike on its many breathtaking trails and enjoy t...

Avg / night: $922. Dog-friendly ocean-view home with grill, wood stove, deck, washer/dryer, & AC | Located in Southwest Harbor, ME | 4.47 Stars | 3 Bed, 2.5 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Take some time to relax and reconnect with nature at this beautifully furnished home in Southwest Harbor! You'll be just a short drive away from the wonderful Arcadia National Park, where you...

Avg / night: $509. Open layout Maine cottage with washer/dryer & grill - dog-friendly | Located in Gouldsboro, ME | 5.0 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Maine's natural beauty is ever-present at The Blue Button Cottage! Nestled near a variety of popular attractions, your days spent exploring Gouldsboro are guaranteed to come with ease. Put on your hiking shoes a...

Avg / night: $596. Charming Coastal House with Cozy Living Spaces and Outdoor Firepit | Located in Winter Harbor, ME | 4.5 Stars | 3 Bed, 2 Bath | No Pets. No pets. Max 6 guests. Nestled in the charming town of Winter Harbor, Maine, this spacious house is the perfect retreat for families seeking a coastal getaway. With plenty of room for everyone to unwind, it's an inviting space where relaxati...

Avg / night: $2,089. Dog-friendly ocean-view duplex with wood stoves, decks, grills, kitchens, ACs | Located in Southwest Harbor, ME | 5.0 Stars | 7 Bed, 5 Bath | Pet-friendly. Dog-friendly. Max 14 guests. Create everlasting memories with your loved ones at this fantastic duplex made up of two separate units! This dog-friendly duplex is in Southwest Harbor, just a short drive away from the wond...

Avg / night: $532. Cozy Cabin with Ocean and Mountain Views, Free Internet | Located in Sullivan, ME | 4.71 Stars | 1 Bed, 1 Bath | No Pets. No pets. Max 2 guests. Escape to this charming cabin in Sullivan, ME, perfect for a romantic getaway for two. Enjoy breathtaking ocean and mountain views from your cozy retreat. The cabin features a kitchenette equipped with essentials like a fridge, micro...

Avg / night: $400. Charming Lakefront House with Outdoor Firepit, Washer/Dryer and Wifi | Located in Gouldsboro, ME | 4.88 Stars | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 7 guests. Escape to this charming lakefront house in Maine, where you can unwind and enjoy stunning water views from your own deck. This spacious vacation rental offers a variety of sleeping arrangements, making it per...

Avg / night: $1,016. Dog-friendly 3-story home with wood stove, deck, grill, ocean views, W/D, AC | Located in Southwest Harbor, ME | 4.88 Stars | 4 Bed, 2.5 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Come and experience a tranquil and unique getaway at this multi-level home in Southwest Harbor! You'll be just a short drive away from the wonderful Arcadia National Park, where you'll be ab...

Avg / night: $842. Dog-friendly oceanfront home with private shorefront, two fireplaces, & firepit | Located in Steuben, ME | 4.86 Stars | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Wake up each morning to a spectacular sunrise view from the privacy of the front porch where you will have amazing views of Bois Bubert Island at this sweet country home overlooking the Atlantic Ocean...

Avg / night: $306. Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking | Located in Hancock, ME | 4.6 Stars | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 2 guests. Escape to this inviting, dog-friendly home in Hancock, ME, where a warm and cozy atmosphere will make you feel right at home. Whether you're relaxing by the gas fireplace or enjoying the fresh air on ...

Avg / night: $1,118. Cozy seaside retreat w/ waterfront deck, expansive lawn, & breathtaking sunsets | Located in Trenton, ME | 3 Bed, 2 Bath | No Pets. No pets. Max 9 guests. Delight in breathtaking sunsets, stunning mountain views, and your own private sandy beach when you book this unique, two-story chic cottage! Nestled at the end of a private road, the cottage sits on an expansive lawn per...

If you have been looking for the perfect partner to navigate the unpredictable beauty of a Maine winter, this 2026 Subaru Outback Limited in Ice Silver Metallic has arrived just in time. It combines the rugged capability of an SUV with the refined comfort of a premium sedan, making it just as comfortable pulling up to a trailhead as it is finding a spot in a crowded downtown parking lot. Becaus...

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Avg / night: $540. Charming Cottage with Cozy Comfort and Easy Access to Outdoor Adventures | Located in Lamoine, ME | 4.64 Stars | 3 Bed, 1 Bath | No Pets. No pets. Max 5 guests. Escape to this charming cottage in Lamoine, ME, where comfort and convenience await you. Featuring cozy sleeping arrangements and all the essentials for a relaxing stay, including a washer/dryer, TV with Netflix strea...

Avg / night: $1,178. Charming Coastal Retreat with Ocean Views, Porch and Private Cabin | Located in Sullivan, ME | 4.0 Stars | 6 Bed, 3 Bath | No Pets. No pets. Max 12 guests. Escape to this serene ocean-view retreat in Sullivan, ME, where coastal tranquility meets modern comfort. The main house offers ample space for relaxation, with a cozy living room, multiple bedrooms, and a fully equipped...

Avg / night: $380. Cozy Cabin with Ocean and Mountain Views, Free Internet | Located in Sullivan, ME | 4.71 Stars | 1 Bed, 1 Bath | No Pets. No pets. Max 2 guests. Escape to this charming cabin in Sullivan, ME, perfect for a romantic getaway for two. Enjoy breathtaking ocean and mountain views from your cozy retreat. The cabin features a kitchenette equipped with essentials like a fridge, micro...

Avg / night: $219. Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking | Located in Hancock, ME | 4.6 Stars | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 2 guests. Escape to this inviting, dog-friendly home in Hancock, ME, where a warm and cozy atmosphere will make you feel right at home. Whether you're relaxing by the gas fireplace or enjoying the fresh air on ...

Avg / night: $426. Charming Coastal House with Cozy Living Spaces and Outdoor Firepit | Located in Winter Harbor, ME | 4.5 Stars | 3 Bed, 2 Bath | No Pets. No pets. Max 6 guests. Nestled in the charming town of Winter Harbor, Maine, this spacious house is the perfect retreat for families seeking a coastal getaway. With plenty of room for everyone to unwind, it's an inviting space where relaxati...

Avg / night: $871. Coastal Serenity Retreat with Ocean Views, Spacious Porch and Modern Comforts | Located in Sullivan, ME | 4.2 Stars | 4 Bed, 2 Bath | No Pets. No pets. Max 10 guests. Discover this serene ocean-view retreat in Sullivan, ME, where coastal tranquility meets modern comfort. Enjoy spacious relaxation in a cozy living room, multiple bedrooms, and a fully equipped kitchen ready for...

Avg / night: $286. Charming Lakefront House with Outdoor Firepit, Washer/Dryer and Wifi | Located in Gouldsboro, ME | 4.88 Stars | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 7 guests. Escape to this charming lakefront house in Maine, where you can unwind and enjoy stunning water views from your own deck. This spacious vacation rental offers a variety of sleeping arrangements, making it per...