Pet-friendly holiday rentals in Waldoboro

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Top-rated pet-friendly home rentals in Waldoboro

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Guest favourite

Guest house in Appleton

4.95 out of 5 average rating, 349 reviews

BRAEBURN at The Appleton Retreat

The Appleton Retreat is a short scenic drive to Belfast, Camden and Rockland. Braeburn at The Appleton Retreat is down a 1/2 mile driveway, on 120 acres of private land, bordered by a 1,300 acre Nature Conservancy reserve. A 25 minute trail leads to a large secluded pond, perfect for a refreshing swim. Braeburn feels like a treehouse, with expansive windows, overlooking woods and wildlife. After a hike, grilling on the porch or dinner out, indulge in your private therapeutic year round hot tub.

6–13 Apr

$207 SGD per night

Guest favourite

Guest house in Washington

4.95 out of 5 average rating, 131 reviews

Fox and Bird Retreat on Davis Stream

Our off-the-grid, solar-powered cottage is nestled within our 18 acres in the town of Washington, Maine. The cottage borders a beautiful stream, is surrounded by tall pines and is several hundred feet away from our home, providing a very private and serene experience. Guests can wander or snowshoe on our property, relax in the screen house next to the cottage or hang by the accessible fire pit. We are close to many local lakes and hiking trails and only 30 minutes from Camden & Rockland.

16–23 Oct

$172 SGD per night

Guest favourite

Flat in Edgecomb

4.91 out of 5 average rating, 298 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

7–14 Nov

$137 SGD per night

Guest favourite

Guest house in Lincolnville

4.97 out of 5 average rating, 328 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

25 Dec – 1 Jan

$185 SGD per night

Guest favourite

Guest house in Orland

4.99 out of 5 average rating, 105 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

16–23 Dec

$144 SGD per night

Guest favourite

Home in Waldoboro

4.85 out of 5 average rating, 180 reviews

Thistledown Farm's Pennysworth - An 1800's barn.

You'll love Pennysworth's ambiance of re-purposed post & beam barn/house, the large stone terrace, indoor and outdoor fireplaces, & huge firepit with an endless supply of wood. There is a huge open kitchen that can easily accommodate multiple chefs. The 2 bedrooms & loft combined can sleep up to 8. Thistledown Farm's location offers fresh & saltwater activities, walking preserves all on our dead-end road. It's a quiet getaway, yet close to all there is to do in mid-coast Maine.

25 May – 1 Jun

$391 SGD per night

Guest favourite

Dome in Jefferson

4.98 out of 5 average rating, 168 reviews

ComfyDome Glamping Hill-Side Site!

Situated on a cozy little hill, you'll be elevated above all the other domes, affording you a "royal" view of the landscape! With a clear view of the sprawling fields, you'll frequently be the first to spot the family of deer that visit ComfyDome. Your heart will be filled with joy at the sight of the newborn fawns walking through the grass. You'll be surrounded by stunning natural beauty on all sides and will have ample open space to enjoy your site in comfort!

13–20 Oct

$173 SGD per night

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.

26 Feb – 5 Mar

$147 SGD per night

Guest favourite

Guest house in Unity

5.0 out of 5 average rating, 193 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

15–22 Feb

$134 SGD per night

Guest favourite

Home in Rockport

4.95 out of 5 average rating, 261 reviews

Sweet home away (pet friendly)

Single floor living at its finest. Conveniently located to both Camden and Rockland, enjoy this 3 bdrm 1.5 bath home in a great country setting. Just 1/2 mile to route 1 and very close to the ocean. Come enjoy the large back deck over looking the peaceful maine woods. The front door in about 50’ from the road, which can be busy at certain time of the day. There is 1 ring doorbell for everyone’s security outside the front door of the house.

16–23 Oct

$233 SGD per night

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.

22–29 Jan

$206 SGD per night

Guest favourite

Place to stay in Owls Head

4.98 out of 5 average rating, 162 reviews

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

21–28 Mar

$196 SGD per night