Vacation rentals with outdoor seating in Wiscasset

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Top-rated outdoor seating rentals in Wiscasset

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 346 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Nov 28 – Dec 5

G$32,218 GYD per night

Guest favorite

Tiny home in Dresden

4.96 out of 5 average rating, 160 reviews

Maplenook Tiny Cabin - A Cozy Woodland Oasis

Escape the hustle and bustle and retreat to the woods with this off grid tiny cabin nestled among a nook of maples. Surrounded by 20 acres of woods with a wide winding walking path to a beaver pond and a stone’s throw away from the Kennebec and Eastern Rivers. This is the perfect little woodland oasis! - 15 minutes to scenic Route 1 + Maine’s beautiful coast, 30 minutes to the Freeport outlets + LLBean Flagship Store and 45 minutes to Portland and the white sandy beaches of Popham and Pemaquid.

Dec 28 – Jan 4

G$23,552 GYD per night

Guest favorite

Cabin in Dresden

4.98 out of 5 average rating, 213 reviews

Merrymeeting Midcoast Cabin

RUSTIC-no running water! cabin perfect for exploring all mid-coast Maine has to offer: 3 hours from Boston or Acadia, 1 hour to Portland and Maine’s gorgeous beaches. 10-30 minute drive to Hiking, swim spots, farm-stands, nationally recognized dairy farms, breweries, restaurants. 5 minute walk from a pickleball court. Stargaze in the hammock by campfire, Grill dinner, check out local tide charts to float in canoe or kayak on the Eastern river. Wood fired oven can be rented for additional fee.

Oct 5 – 12

G$23,440 GYD per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Mar 20 – 27

G$33,516 GYD per night

Guest favorite

Guesthouse in Bath

5.0 out of 5 average rating, 113 reviews

Waterfront Sunrise Cove Cottage

Unwind and enjoy spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! Less than 30 minutes to Popham Beach, this is the perfect home base for a midcoast Maine getaway. The cottage has a post-and-beam design, cozy furnishings, and expansive views across the field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river, and nights are full of stars. Best for 2 adults or a small family. Owners live on property with small dog.

Dec 27 – Jan 3

G$33,022 GYD per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

May 10 – 17

G$27,954 GYD per night

Guest favorite

Guest suite in Woolwich

4.92 out of 5 average rating, 187 reviews

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking, comfortable queen bedroom, Wifi; fully equipped kitchenette; spacious bathroom with large jacuzzi tub and separate walk-in shower. Roomy sitting/dining area opens out onto deck with Adirondack chairs; table and grill. Large smart TV. Fast Wi-Fi. Firepit.

Jul 28 – Aug 4

G$21,071 GYD per night

Guest favorite

Cottage in Wiscasset

4.87 out of 5 average rating, 211 reviews

Waterscape Cottage - private waterfront

A picturesque cottage perched on the hillside and visible as you cross the Davey Bridge. Elevated panoramic views of the Sheepscot R. and Wiscasset Harbor. When the Prince of Thailand owned the property the cottage was staff quarters! A rustic, comfy, quiet and peaceful little 2-story on 34 acres of woodlands. IN the woods so you may encounter creatures out and about - porcupine, ticks, mosquitoes, ants, fox, birds of prey and our hens, bees or dogs : ) 2 quiet furry friends welcome.

Jan 13 – 20

G$36,986 GYD per night

Guest favorite

Apartment in Damariscotta

4.94 out of 5 average rating, 339 reviews

Cottrill House on Damariscotta River # 1

Cottrell House/Studio. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, off street parking, private bath, living room with mini fridge, microwave and coffee maker. Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board right across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. This is non smoking property!

Dec 5 – 12

G$22,063 GYD per night

Guest favorite

Guesthouse in Wiscasset

5.0 out of 5 average rating, 262 reviews

Recharge at Tranquil Sea Salt Cottage in Historic Wiscasset

Grab a book and curl up in the swing seat overlooking idyllic lawned gardens at this serene abode. Browse the owner’s fine art studio gallery on the property, then walk to local landmark “Red's Eats” for an iconic lobster roll. Wiscasset village hosts fantastic boutique shops, antique stores, art galleries, wine bar, restaurants all within walking distance. And just up the road is “The Alna Store”recently nominated for a James Beard Award!

Oct 1 – 8

G$50,637 GYD per night

Guest favorite

Guesthouse in Richmond

4.9 out of 5 average rating, 138 reviews

The Studio

Welcome to our 2.5 acre haven! This studio is full of life with color that will bring your spirits up. It is a little over 400 sq. ft. with your own private entrance from the garage and above apartment, on the first floor, your own parking and not too far from the city. Richmond is a small town that sits near the Kennebec River and Swan Island where you can enjoy outdoor adventures. * Space not equipped for children *

Apr 6 – 13

G$21,901 GYD per night

Guest favorite

Apartment in Damariscotta

4.92 out of 5 average rating, 255 reviews

Fernald's Backside

Fernald's Backside is a sunny, comfortable 2nd floor apartment , tucked behind S. Fernald's Country Store in the heart of downtown Damariscotta. It features a deck with views of the Damariscotta River and Harbor. A one bedroom apartment with ample living space and full kitchen, it can sleep 5 with a double and single bed and a sleeper sofa. Fernald's Backside is Pet free.

Nov 2 – 9

G$24,476 GYD per night