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, 560 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, 396 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.

Guest favourite

Home in Portland

4.95 out of 5 average rating, 135 reviews

Lovely 3Bdrm Home w/ AC & BBQ 10min to DT Portland

Enjoy your visit to Portland at our beautiful, newly renovated home, equipped with everything for a perfect, stress-free stay! This spacious, stylish house has lots of natural light, a fully-fenced backyard with a firepit and BBQ, laundry, a full kitchen, and a double farmer’s porch! There is a desk and wifi, perfect for guests working from home! Get to downtown Portland in 10 minutes, where you will find coffee shops, great bars and restaurants, museums, shopping, and plenty more to explore!

Superhost

Home in West Bath

4.86 out of 5 average rating, 105 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.

Guest favourite

Home in Bucksport

4.9 out of 5 average rating, 101 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!).

Superhost

Campervan/Motorhome in Blue Hill

4.85 out of 5 average rating, 20 reviews

Pampered Camper

Reconnect with nature at this unforgettable escape. 30 miles to Acadia National Park this RV gives you a quiet place to rest after a busy day of hiking and enjoying all Maine has to offer. Come back to a place where you can enjoy the beautiful big back yard space, reclining leather sofa, king size memory foam bed, full size refrigerator, gas stove and a fireplace. Wifi, Grille, and private parking. Pampered Camper also has fun little surprises for our guests to make you feel truly pampered.

Guest favourite

Campsite in Friendship

4.86 out of 5 average rating, 29 reviews

Seaside Glamping in Retro Camper for 2 guests

Glamp in style in our vintage camper at Snug Harbor Camps! The 1959 Trotwood is bursting with retro flare, and sits on a tidal cove minutes from bustling Friendship Harbor, where lobsters are the daily catch. Your coastal vacation will be complete with our firepit and Adirondacks, hammocks, kayaks, rowboat, and beach. Enjoy the beautiful landscape, vintage nautical decor, and all the necessities to enjoy oceanside glamping in midcoast 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, 104 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, 211 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.

Guest favourite

Tent in Freeport

5 out of 5 average rating, 9 reviews

Large, luxurious glamping tent - 14

Enjoy a luxury outdoor camping experience like no other! Sleep out in nature in our 16'x20' luxury glamping tent with a queen bed, queen sleeper sofa, and a seating area. Located in a recently renovated luxury campground with tall northern pines all around. It has a front porch with comfy chairs and a charming outdoor seating area with a fire ring, bistro lights, and Adirondack chairs.