Holiday rentals with outdoor seating in Waldoboro

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Top-rated rentals with outdoor seating in Waldoboro

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in East End

4.96 out of 5 average rating, 559 reviews

Peaceful Oasis on Munjoy Hill -1st flr/3BR+parking

Spacious, light-filled 3 Bedroom/1 bath 1st-floor apartment with tasteful art, contemporary furnishings, + a well-appointed kitchen. Fantastic location! -A 5-minute walk to the Eastern Promenade with its food trucks, beach & scenic trails -Nearby are bakeries, cafes, world-class restaurants and popular breweries -Relax in the serene garden w/ outdoor seating -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

Guest favourite

Flat in East End

4.96 out of 5 average rating, 394 reviews

Munjoy Hill, East End 1 BR Portland, ME

The Portland Observatory marks your way home to this apartment atop Munjoy Hill. Furnished for guests, private entrance, 1st floor unit of our 2 unit home of twenty years. BEST LOCATION! Skip the car. WALK to restaurants, music, shops, breweries, beach, parks, & historic Old Port. Stones throw to fresh produce, bakeries, wine & spirits. Furnished with LOCAL ART (made by your host in adjacent studio) the cozy apartment offers humble elegance. Just arrive, fun awaits. All are welcome here.

Superhost

Home in West Bath

4.86 out of 5 average rating, 104 reviews

Oak Leaf

Take it easy at this unique and tranquil getaway. This sweet cottage offers scenic water views and much more. Overlooking the New Meadows river, it is nestled in a quiet area and surrounded by 100 yr old oak trees. It is loaded with charm yet offers modern amenities. You feel tucked away, yet the place is only 10 to 20 minutes from beautiful beaches, hiking, fine dining, and shopping opportunities. Enjoy beautiful sunsets from the back porch and cozy up to fire pit while you make memories.

Superhost

Flat in Downtown Portland

4.88 out of 5 average rating, 169 reviews

The LUXE Treehouse

This charming West End top-floor unit offers privacy and style, highlighted by an expansive rooftop deck. A true urban oasis, the deck is perfect for unwinding with cocktails or having a morning coffee. Located in one of Portland’s best neighborhoods, you’ll be within walking distance of the waterfront, plus top-rated restaurants, museums, and music venues. With its prime location and inviting outdoor space, this is the perfect place to experience the city and the beach is just 10 min away.

Guest favourite

Home in Bucksport

4.92 out of 5 average rating, 100 reviews

Maine Wilderness Oasis: Hike Swim Kayak Fish

Take it easy at this unique getaway. Spend your days hiking the backyard trails (25 acres behind the house!), swimming or paddle boarding on the lake with a private dock (lake is a 2 minute walk down the driveway!), or traveling to near by coastal towns like Bar Harbor (Bucksport was voted #1 small coastal town in USA!). For dinner, stop by one of the lobster shacks just down the road to bring home your fresh Maine lobster! Come and disconnect (or stay connected if you’re working remotely!).

Guest favourite

Cottage in South Thomaston

4.95 out of 5 average rating, 104 reviews

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Superhost

Flat in Boothbay

4.92 out of 5 average rating, 223 reviews

Farnham Point Retreat

New modern apartment over garage. Brand new patio and fire Pit area. Nestled in the woods. 10 minutes from downtown scenic Boothbay Harbor and Botanical Gardens. Near Carriage House Restaurant. Near Ocean Point. Large walk-in closet. Two large flat screen TVs. BBQ Grill, Fire Pit, and outdoor Dining area with table and chairs. Corn hole and ring toss games. Firewood in the shed for guests. Outlet for EV charger available for small fee, upon request.

Guest favourite

Guest suite in Penobscot

4.88 out of 5 average rating, 109 reviews

Waterfront Getaway on the coast of Maine.

Cozy waterfront, two bedroom apartment with separate entrance and private deck overlooking the beautiful Maine coast. Walk the shore path through a field, filled with wildflowers, to a private cove on the Bagaduce River. The light filled apartment is located above the garage of a restored antique farmhouse and has beautiful water views from the living room and private deck. The perfect spot for a relaxing vacation on the coast of Maine.

Guest favourite

Tent in Liberty

5 out of 5 average rating, 11 reviews

Porcupine Creek Rustic Camping - Owls Nest

The Owls Nest Tent is a luxury platform tent that sits on a rise overlooking a small field. Inside, there is a comfortable queen-sized bed. Outside, the tent canopy extends over the tent deck to provide a shaded place to sit in one of two comfortable Adirondack chairs. This is a perfect place to enjoy a morning cup of coffee or afternoon cup of tea! Additional information can be found on our website: Porcupine Creek Rustic Camping

Top guest favourite

Home in Yarmouth

4.93 out of 5 average rating, 54 reviews

New Home by Breweries, Outlets, and Portland Food!

Newly renovated and centrally located in charming Yarmouth Village! Enjoy a short walk to shops and restaurants, drive 15 minutes to Portland Old Port and renowned restaurants, or 5 minutes to Freeport Breweries/Outlets. Maine Beer Company, Mast Landing, LL Bean, Ottos, Royal River Grill all just minutes away. This is the perfect pit stop on your way to Acadia/ski mountains or to plan a day trip up the coast to Boothbay Harbor.

Top guest favourite

Guest house in Newcastle

4.98 out of 5 average rating, 103 reviews

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!

Guest favourite

Flat in East End

4.86 out of 5 average rating, 210 reviews

Secret Garden

2bed, 1bath-2nd Floor Unit. Located in the middle of Portland's most desirable neighborhood - the top of Munjoy Hill in the East End of Portland. Hardwood floors throughout. The double lot offers a LARGE and PRIVATE fenced in yard, complete with 2 patios/sitting areas, a grill, and beautifully maintained flower/vegetable gardens. One off street parking spot and city bus stop on the street.