Pet-friendly holiday rentals in Winterport

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 800 Mbs fiber 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. We’re very pet friendly!

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

King Bed|Historic DTWN Hotel|Fiber Internet (FAST)

1873 historic hotel that sits in the heart of downtown Bangor. Just steps from fantastic restaurants, breweries, & coffee shops! 1/2 mi. to Amphitheater *10 minute walk* 43 mi. to Acadia Nat'l Park 3 mi. to Bangor Airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ Plush King-sized bed w/ high end Centium Satin linens ☀ High Speed Fiber Internet ☀ 50” Roku TV w/ HULU + ☀ Desk ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

Lakefront Cottage on Tracy Pond

Lakefront cottage on 47 acre Tracy pond. The pond has no public access so it is quiet with only my home and another Air BnB on site. You share the backyard with my home. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

Lakefront Gem with Breathtaking Island Views

You didn’t know you needed this- until you arrived. A modern studio tucked right on the water’s edge, where nothing is between you and the lake but loons, sunlight, and a whole lot of time to just be. Private dock (float, fish, float again) Spa-style indoor + outdoor showers (yes, both. Why not?) Outdoor movie night under a blanket of stars Pet-friendly Swimming, stargazing, and stories you’ll be telling next year Just a short drive from town or Acadia — if you ever want to leave.

"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.

Harborview Escape Downtown Belfast

Enjoy a bright, sun-filled, stylish experience at this centrally-located 2nd floor apartment. This open concept, king bed studio apartment is perfect for a couple or a solo experience. (The bedroom space is defined but does not have a door.) Spacious and cozy with a well-appointed kitchen and washer/dryer. Lots of restaurants & shops nearby with a superb coffee bar downstairs. Belfast waterfront, Saturday morning United Farmers Market, and the fabulous Harborwalk just 2 blocks away.

Field of Dreams Tiny Home

Cozy Tiny Home with Stunning Views Escape the hustle and bustle in this charming tiny home with serene field views. Enjoy the tranquility of nature while still being conveniently located just minutes from Bangor's airport and town center. Relax and unwind in the private Jacuzzi with stunning views of the endless field or gather around the fire pit for a cozy evening under the stars. The projector screen offers endless entertainment options, perfect for movie nights or gaming.

Waterfront Tipi Glamping // Phoenix Landing

Majestic private waterfront Tipi * on a lake. Quiet nature oasis with hot tub, woodstove, firepit, modern grill, and all the essentials. Ice skate or xc-ski across the frozen lake and watch the bald eagles fly overhead, or relax in the Adirondack chairs in front of the bonfire while you make smores and cook dinner on the grill or over the open fire, then snuggle up inside the tipi while you listen to vintage vinyl and let the owls hoot you to sleep. *Tipi closed March-April.

Modern RV on Tracy Pond

Peaceful, spacious RV parked in a wooded setting on Tracy Pond. You have all the comforts of home plus a beautiful setting in this 30 foot trailer. Full kitchen, comfy theater seating with a great WiFi connection. You can fish in the lake, or use the kayaks to watch the eagles soar and otters play. You have a fire pit and large picnic table to enjoy the outdoors. Only 15 minutes to downtown Bangor and the airport. One hour to Acadia National Park.

Graham Lakeview Retreat

Escape to the beauty of coastal Maine in this peaceful and fully-equipped waterfront home—just 40 minutes from Acadia National Park. Enjoy serene water views, launch one of the provided kayaks, or soak in the jacuzzi tub after a day of hiking. Ideal for couples, families, solo travelers, and your four-legged friends, too! Whether you're here for the national park, the coast, or just a quiet escape, this welcoming retreat has everything you need.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.