Holiday rentals in Wiscasset

4.98 out of 5 average rating, 243 reviews

Cabin in Dresden

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.

4.89 out of 5 average rating, 209 reviews

Flat in Richmond

Designers Dream 1br Apt where class meets relax!!!

This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.

4.91 out of 5 average rating, 116 reviews

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

4.97 out of 5 average rating, 101 reviews

Flat in Bath

1820s Maine Cottage with Garden

Enjoy your stay in a cozy, shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own private entrance and contains one bedroom, one bathroom, a full kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer!

4.98 out of 5 average rating, 282 reviews

Cottage in Edgecomb

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.

4.98 out of 5 average rating, 161 reviews

Townhouse in Wiscasset

Retreat at Sea Cloud Cottage in Historic Wiscasset

Welcome to Sea Cloud Cottage - A Charming Retreat in Wiscasset, Maine Sea Cloud Cottage is a beautiful one-bedroom home, once the guest house to the larger Acorn Cottage next door. Perfectly designed for a couple or small family (with an extra child or adult on the pull-out sofa), this 900-square-foot gem offers an inviting, comfortable space for your getaway. You can also rent it alongside Acorn Cottage for larger parties, accommodating up to 9 guests.

4.85 out of 5 average rating, 517 reviews

"Ship Shape": waterfront, cozy studio- downtown

Located in a historic 200 year old building "Ship Shape" is close to downtown but on a quiet tree-lined residential street. It is just one block to the library, bookstore, post office and all the lovely shops. It is on the shore of the Damariscotta River with wonderful views from inside and out.. You’ll love my place because of the neighborhood, the light, the outdoor space, and the comfortable bed. My place is good for couples and solo adventurers.

4.91 out of 5 average rating, 191 reviews

Apartment in Edgecomb

A Spacious Vacation Cottage in Sheepscot Harbour

A large and stylish one bedroom cottage with water views. Newly renovated and offering style and convenience. Located within walking distance to Wiscasset. A great home base for exploring Boothbay Harbor and many more midcoast Maine destinations! Plan a day excursion, or relax inside with the view of the harbor. Make yourself at home in the cottage! Enjoy and walk the resort common areas including a gazebo, riverside lawn, and a 100 ft pier.

4.88 out of 5 average rating, 274 reviews

Cottage in Wiscasset

Waterscape Cottage - private waterfront

This is where you want to stay! Away from all the traffic and noise of HWY 1, down a long driveway but super close to the village. Perched on the hillside with elevated panoramic views of the river and Wiscasset Harbor. This adorable little building is post and beam construction - comfy, quiet, peaceful on 34 acres of woodlands and river front. Want to squeeze in more kids? Talk to us. 2 quiet nonaggressive furry friends welcome.

4.98 out of 5 average rating, 106 reviews

Guest house in Newcastle

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!

4.92 out of 5 average rating, 203 reviews

Mystical Mary Howe Room, Downtown Damariscotta

This spacious studio apartment is perfect for relaxing after a day of exploring beautiful Damariscotta and surrounding communities. Situated on the third floor of one of Damariscotta's many historical buildings this apartment consists of a large living room area with kitchenette and a separate large bedroom with bath. Parking is right next to the building and a key will be provided for your apartment.

4.92 out of 5 average rating, 286 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.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Wiscasset holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Wiscasset

Home in Wiscasset

5 out of 5 average rating, 4 reviews

Lilac Cottage

BeckiRating, 5 stars8 months ago

If you adore old homes that are charming, and laid out in an old time way, you will love this place! If you want a contemporary space, pass it by. But you are missing a piece of history! Everything you need is available and the sheets and towels and new. Plus the location is the best as it is not far from the Maine coast and numerous charming New England towns!

4.99 out of 5 average rating, 70 reviews

Cottage in Edgecomb

Coastal Cotton Cottage on Sheepscot Harbour

DerrickRating, 5 stars6 months ago

Great location and a beautiful property. Very comfortable and feels like you are at home when you walk in.

Apartment in Wiscasset

4.92 out of 5 average rating, 13 reviews

Green Gables, garden bliss in Maine's sea air

ChristinaRating, 5 stars2 weeks ago

We stayed a long weekend over Memorial Day and Rob’s place was the perfect launching spot for us to be able to enjoy the entire Midcoast area without spending too much time in the car. The kitchen was well stocked, the beds were comfy and the beautiful yard was an added bonus. I loved walking next door to Treats, getting a cappuccino and enjoying it on the front porch while the church bells rang. Rob was very responsive and allowed us to check out at a later time, which was very helpful and much appreciated! Thank you! We’ll definitely be back:)

4.97 out of 5 average rating, 79 reviews

Tiny home in Edgecomb

Waterfront Cottage in Mid-coast Maine

BarbaraRating, 5 stars3 weeks ago

I escaped to Sara's for a couple days of quiet and solitude, and I chose the perfect spot. The cottage is clean, comfortable, and in a great location with a fine view. The coast of Maine is beautiful even when it's cold and foggy in the middle of May!

Flat in Wiscasset

4.76 out of 5 average rating, 107 reviews

Waterview Studio | Next to River and Antique Shops

JoniRating, 5 stars8 months ago

We really enjoyed our stay. As other reviewers have said, there were steep steps up to the second story apartment so we were prepared for it. The house is on a beautiful street and was super quiet at night. The dedicated parking spot was nice and you could see the line at the front of Red's right from the windows. The owner was so nice and told us we were free to use her lovely patio whenever we wanted. We would stay again.

Flat in Edgecomb

4.75 out of 5 average rating, 12 reviews

The Lighthouse Keeper’s Sanctuary

MaryRating, 5 stars2 weeks ago

What a lovely night we had at Caroline’s place. Comfy bed, great pillows, beautiful view. Very clean, convenient access/parking, great directions from the host. Lots of nice touches!