Holiday houses in Waldoboro

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Top-rated holiday rentals in Waldoboro

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Guest favourite

Guest suite in Thomaston

4.86 out of 5 average rating, 110 reviews

Private Top Floor Waterfront Apartment

Welcome to Gabriel's Anchor! 10 min walk to Main St, 10 min drive to Rockland, 2 min walk to public overlook, across the street from the lively Slipway Restaurant, on the waterfront. Gabriel's Anchor is great for couples, families, and solo adventurers looking to stay in the heart of the wonderful coastal Thomaston, Maine. 2 bdrm/1bath. 1 king bed & 1 double. kitchenette has a stovetop, fridge (no freezer, but feel free to use ours if needed), cooking utensils, dishes, coffee maker & coffee.

10 – 17 May

$1,150 AUD total

Guest favourite

Guest suite in Round Pond

4.79 out of 5 average rating, 107 reviews

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

29 Dec – 5 Jan

$1,172 AUD total

Guest favourite

Apartment in Nobleboro

4.89 out of 5 average rating, 137 reviews

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

16 – 23 Sept

$1,335 AUD total

Guest favourite

Apartment in Damariscotta

4.94 out of 5 average rating, 338 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!

16 – 23 Mar

$1,339 AUD total

Guest favourite

Home in Appleton

4.96 out of 5 average rating, 122 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

21 – 28 May

$1,771 AUD total

Guest favourite

Guest suite in Damariscotta

4.93 out of 5 average rating, 149 reviews

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.

7 – 14 Jan

$1,318 AUD total

Guest favourite

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

Salty Dog Hilltop Guest Suite (permit #SDR22-18)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

21 – 28 Nov

$1,853 AUD total

Guest favourite

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes gets you to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOGS

3 – 10 Oct

$1,224 AUD total

Guest favourite

Apartment in Damariscotta

4.92 out of 5 average rating, 252 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.

12 – 19 Mar

$1,411 AUD total

Guest favourite

Cabin in Nobleboro

4.94 out of 5 average rating, 108 reviews

Waterside Cabin the Woods 50 acres-No hidden fees!

Enjoy Maine cottage living the way it used to be! Our 100+ year old cabin is 20'x20' with a kitchen ell and 8'x20' enclosed porch with deck. Kitchen with gas stove, sink. fresh spring water. Gas lighting, no electricity, linens included. Outdoor shower with hot water. Composting toilet. Dock, canoes, paddleboat. Very private setting yet just 10 minutes to Damariscotta.

23 – 30 Sept

$1,821 AUD total

Guest favourite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

17 – 24 Oct

$1,033 AUD total

Guest favourite

Cabin in Camden

4.83 out of 5 average rating, 706 reviews

Cozy Village Cottage

Cozy, isolated, well stocked cottage cleaned by a professional cleaning crew awaits your visit. Need a quiet, inexpensive 'get away' where you can work and relax? Contact for long term stays this winter and alternatives to the week long requirement.

25 Feb – 4 Mar

$1,173 AUD total