Home Vacation Rentals By Owner In Deer Isle, ME

Showing 40 Of 51 Vacation Rentals
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Exceptional(6)

$281.21

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Private Vacation Home

Waters Edge- Oceanfront Farmhouse in Deer Isle

Deer Isle, Maine, United States

A classic, oceanfront farmhouse in Deer Isle. Water`s Edge is cozy, clean and comfortable. This laid back Deer Isle setting is sure to be relaxing and refreshing.Water’s Edge is a classic farm house overlooking the island of Stonington – the home has a unique position at the end of Deer Isle as you pass over to Stonington. Water Edge has a couple hundred feet of shore frontage which makes it great for kayakers or water faring folks. brbrWater’s Edge is a two bedroom one and a half bath farmhouse with nice views and central island position – making it easy to get to Deer Isle or Stonington villages from this location. The home has a nice first floor with a gallery style kitchen (yes – there is a lobster kettle). The home has a comfortable living room with couch and arm chair and a formal dining room with seating for six. Rounding off the first floor is a half bathroom with a sink and a flush. brbrThe second floor of Water’s Edge has two bedrooms and a full bathroom. The first bedroom has a queen sized bed, a dresser and closet. The second bedroom has two twin bed and a full bed. This room also has a dresser, a closet and nice views of the cove. brbrWater’s Edge is an affordable oceanfront option in Stonington. Come and unwind in this sweet little cottage by the ocean’s edge.brbr* Please note that if you elect to book this property you will be expected to sign a vacation rental agreement with The Island Agency. For specific terms of the agreement inquire before using the Book Now feature as the expectation of having a returned agreement within 7 days of reservation.Ocean Frontage - Good place to launch kayaks-Coffee Maker, Toaster, Dishwasher-Outdoor Cooking - Gas Grill -Wireless Internet, Cable Television -Washer and DryerThe Island Agency is located on Main Street in Stonington village. We are available to our guests through phone, internet and in-person during your stay.Water`s Edge location is central to Deer Isle or Stonington village. Classic farm house with many recent updates provides for very comfortable accommodations.Deer Isle is a bridged island, easily accessible by car. The island does not have public transportation so a car is highly recommended for your stay. The closest public airports are Bangor International and Hancock County-Bar Harbor.Deer Isle and Stonington have many awesome hiking trails and preserves. If you like hiking, biking, sightseeing and boating then this is the place to be.
Bed 2

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Bath 1

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Sleep 6

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Exceptional(2)

$326.38

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Private Vacation Home

Sherwood Cottage-Along the Shores of Penobscot Bay

Deer Isle, Maine, United States

Sherwood Cottage is a ranch-style home nestled along the shores of Penobscot Bay. This classic Maine cottage offers stunning south-facing oceanfront views, a brick fireplace, screened in porch and completed with a sandy pocket beach located on 751' of picturesque water frontage. Private and peaceful, this home invites you to slow down, reconnect with nature, and embrace the simplicity of life.brbrSherwood Cottage is a three-bedroom, two-bathroom house which sits in a wooded, seaside location in the Sunshine area of Deer Isle. It has been a cherished family heirloom for generations with the owners opening the doors to guests when they are unable to visit. Sherwood Cottage offers many of the qualities that make for an ideal vacation retreat: ocean views, a private beach, outdoor screened porch, a cozy fireplace as well as the option to bring your family pet.brbrThe home is designed for easy, one-level living. On the ground floor, you'll find two bedrooms, a well-equipped kitchen, a comfortable living room and a laundry area. The kitchen features all the essentials for preparing meals and there is a dishwasher to take the sting out of the clean up process.brbrThe first bedroom is furnished with a King-sized bed, dresser, and closet plus a private ensuite bathroom with a shower/tub combo. The second bedroom offers a Queen-sized bed, dresser, and closet, with access to a full bathroom featuring a tub/shower combo. The third bedroom is located on the second floor and includes both a King-sized bed and two Twin-sized beds. brbrSherwood Cottage offers plenty of outdoor activities to help you fully enjoy the natural beauty of the area. Guests have exclusive access to the private pocket beach. In addition the owners provide bicycles and two kayaks for your use (at your own risk). For relaxation, you can unwind on the deck which enjoys ocean views on the screened-in porch, which provides shade and protection from the sun, as well as from summer bugs.brbrSherwood Cottage is the quintessential Maine getaway—seaside, serene, and off the beaten path. Reach out today to reserve your summer escape at Sherwood Cottage.
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Bath 2

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Sleep 9

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$322.83

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Private Vacation Home

Shangri-La - Private, Oceanfront Home, Deer Isle

Deer Isle, Maine, United States

*Shangri-La*, a treasured family home nestled on the shores of Brays Narrows, near Long Cove and the scenic waterways of Deer Isle. With its nostalgic vibe, this well-kept waterfront retreat which blends retro charm with modern comfort.brbrShangri-La* boasts four bedrooms and two bathrooms, offering plenty of space to stretch out. On the first floor, you’ll find a cozy queen bedroom, a handy ¾ bathroom (shower stall), and a spacious living area. The living room, complete with a decorative (non-functional) fireplace and large sliding doors, opens onto a seaside deck with a patio set—perfect for enjoying the view over dinner or morning coffee. The kitchen, while timeless, comes fully equipped, including a dishwasher and a quaint breakfast nook for lazy morning meals.brbrUpstairs, there are three additional bedrooms. One has a full bed and playful nautical touches, another features a queen bed and a private balcony with sweeping ocean views, while the third holds a full bed with plenty of clothing storage. The second-floor bathroom features a full tub/shower combo.brbrBut that’s not all. The lower level has a game room where you can challenge friends to some air hockey, ping pong, a game of pool or break out a classic board game.brbrOutside, a small lawn surrounds the home, and just down the driveway, you’ll find access to a private boat launch and cove. Two kayaks are available for your use—just be mindful of the tide to avoid any mishaps. brbrIf you’re looking for a fun getaway with waterfront beauty, *Shangri-La* is calling your name. Reach out to learn more or book your stay!
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Bath 2

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Sleep 8

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Exceptional(7)

$730.3

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Private Vacation Home

Light-Filled Oceanfront Home Offering Stunning Views of Penobscot Bay

Deer Isle, Maine, United States

Immerse yourself in the enchanting beauty of Deer Isle from this delightful 3-bedroom house. Nestled atop Northwest Harbor, Fairwinds is a charming waterfront property just a stone’s throw away from Deer Isle Village. This modern cottage features an open and airy living space that offers breathtaking views of Penobscot Bay and the surrounding islands. Private stairs lead to a tranquil cove below, inviting you to explore the quintessential Maine Coastline. Whether you’re a kayaking enthusiast or simply seeking a peaceful spot to hunt for beach treasure, this place is the perfect getaway.brbrFairwinds is a meticulously appointed three-bedroom, three-bathroom home featuring a fully completed walk-out basement. The basement includes a billiards/ping-pong table, and a compact kitchenette with a bar area. A three-season screened-in porch and expansive deck with a grill provides ample outdoor space for relaxation and entertainment. The property also includes two stone patios and a fire pit, inviting guests to enjoy the natural surroundings. Fairwinds comfortably accommodates up to eight guests and is equipped with high-speed internet.brbrUpon arriving at Fairwinds, guests will be delighted to find ample parking space for four vehicles. A small mudroom welcomes guests to remove their shoes before entering the main living space. The room features an LG washer and dryer, as well as a deep sink.brbrThe home’s entrance leads to a spacious great room, a dining area, and a kitchen with soaring cathedral ceilings and sky lights. The decor combines coastal charm with eclectic coziness.brbrAt the heart of the home lies a stunning Deer Isle granite hearth and gas fireplace flanked by built in bookcases. Cozy seating beckons one to unwind with a board game, embark on a jigsaw puzzle, or enjoy a show on the 54-inch smart TV. A reading nook, tucked away in the living area, offers a haven for book lovers, complete with an extensive collection of books suitable for all ages.brbrThe dining area rests in the center of the home with a farm style table and seating for eight to ten people. Beyond that is the well equipped kitchen with a spacious granite island, a Bosch gas stove and oven, a Sub-Zero fridge and an ultra quiet Bosch dishwasher.brbrFrench doors open to the three-season screened-in porch, featuring glass windows that overlook the tranquil waters of Penobscot Bay. A seating area is conveniently located for enjoying morning coffee or tea, while an oval table accommodates six guests. For extended outdoor entertaining, a screen door leads to a charming deck equipped with a Weber Grill.brbrThe master suite on the east side of the home features a standalone tiled shower, double vanity sinks, built-in dressers, and a separate toilet area. A walkthrough dressing area with ample space for hanging clothes separates the bedroom area from the rest of the suite. The bedroom boasts a spacious California King bed, and windows surrounding the room offer breathtaking views of the water.brbrThe West side of the house features a bedroom with two extra-long twin-size beds that overlook the enclosed potager garden. The third bedroom offers a comfortable queen-size bed and provides a stunning view of the water. A bathroom with a tub and shower is conveniently located next to the bedrooms.brbrThe lower level of the home spans 1400 square feet and features a lounge area complete with a billiards/ping pong table and a bar/mini kitchen equipped with a dishwasher, sink, toaster oven, and microwave. A living/sleeping area accommodates a queen-size pull-out sofa and a twin-size bed. For an immersive movie experience, there is a large smart TV with surround sound. A curtain can be drawn to provide privacy from the lounge area. A spacious full bathroom with a large shower completes the lower level amenities.brbrTwo stone patios, perched above the breathtaking 200-foot waterfront on Penobscot Bay, offer a perfect spot to unwind and enjoy the spectacular sunsets. Evening cocktails while watching the sunset is a popular pastime among guests.brbrTall oak trees shade the lawn area, perfect for playing games of croquet or bocce. Stairs lead to the rocky shorefront, ideal for launching kayaks, paddle boards, or canoes. Unfortunately, due to insurance restrictions, we are unable to provide guests with any water equipment. However, we welcome guests to bring their own boats or rent from local establishments on the island.brbrA haven for nature enthusiasts, Fairwinds offers an array of captivating activities to explore the enchanting Maine landscape. With binoculars in hand, you can witness the playful seals bobbing in the bay, observe the Ospreys nesting near the pond across the way, and even catch a glimpse of majestic bald eagles perched gracefully in the trees along the shore.brbrFairwinds offers an unparalleled escape into the captivating beauty of Deer Isle. Whether you're seeking a peaceful retreat with stunning views or an adventure on the Maine coastline, this charming home provides the perfect setting for a memorable getaway.
Bed 3

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Bath 3

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Sleep 8

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Exceptional(2)

$564.57

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Cottage

Eastman's Seaside Cottage with Private Beach

Deer Isle, Maine, United States

With panoramic ocean views on a 4 acre property, this historic beachfront Deer Isle, Maine cottage -- renovated in 2021 -- transports you to a cozy and character filled seaside paradise. Watch the sunset over the water from the expansive deck, make s'mores around the firepit, head down the stairs to the private beach and collect shells or launch a kayak, or sit in the living room by the wood burning stove. There are 5 bed bedrooms, a living room, and a separate kid den with smart TV.brbrWe are at the top of Deer Isle with a large private beach just a few steps down from our front yard with large deck and fire pit. The cottage was originally built by our grandfather in 1970's and renovated in 2021 with a massive addition. It's a mix of old and new, with furniture and Maine needlepoint artwork throughout that were built by our grandparents but with all the modern amenities you need to feel comfortable, including two smart TVs and wifi. We are just a short drive from Stonington where you can check out local art galleries and antique shops or pick your own lobster. Yes, we have everything you need to cook your lobster at the cottage!brbrYou will need a car to get around, there is plenty of parking on the property.brbrWe are based in Washington, DC but have a local caretaker who can come over and help with anything you might need during your stay.brbrDeer Isle is located in the Penobscot Bay and is part of the traditional territory of the Penobscot Nation. It's natural beauty is breathtaking--walk along the shell filled beaches, hike the granite quarry, kayak or stand-up paddle board off our private beach (you must rent your own kayaks) or you can drive into Stonington and kayak or SUP in the bay. Stonington which is a short drive from the cottage is dotted with antique shops, restaurants, art galleries, and of course the Stonington Opera House. It is also an authentic fishing village filled with lobster boats and delicious fresh lobster. Within a 5 minute drive from the cottage we also have a small grocery store, a lobster shack, a burger shack and playground, a local coffee shop, and art galleries.brbrYou will need a car to get around.brIt's rugged deep woods setting so we request that you consider removing your shoes when inside keep the dirt away. There is a generator to restore power in the event of severe weather. Thank you
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Bath 2

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Sleep 10

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$590.39

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Private Vacation Home

Oak Point Cottage- Bold, Southern Facing Ocean Frontage

Deer Isle, Maine, United States

**NEW RENTAL FOR 2026**brOak Point Cottage is a private home in a quiet, off the beaten path island location. The home has bold, southern facing ocean frontage on the Eggemoggin Reach and Fish Creek Cove. Guests will enjoy easy access to a beach great for kayaking, boating or for the brave: swimming! Oak Point Cottage has beautiful yard spaces, making this property a joy for those who are seeking a water connection. Enjoy all the wonders of being on an island in Maine from this unique and scenic location in Deer Isle. brbrOak Point Cottage is a three bedroom, two bath home located beyond Reach Beach on the shores of Deer Isle. The home has bold ocean frontage and a contemporary construction offering bountiful natural light for many of the living spaces and bedrooms. A one level floor plan makes it easy to enjoy all that this property has to offer. brbrThe kitchen, dining area and living space have a nice open concept making it wonderful for evening dinners or morning coffee. The kitchen has all the essentials in place to make meals from home (think seafood)! There is a dining table for 6-8 people and a series of comfortable seating options in the living room area that make this gathering space comfortable and inclusive. brbrThe home has three bedrooms. The first bedroom has two sets of bunk beds, a dresser, closet and lamp. The second bedroom has two twin beds, ocean views, a closet and a dresser. The third bedroom, the primary room, has a queen size bed, dresser, big ocean views as well as a door that leads out to the ocean view deck system. The primary bedroom has an ensuite bathroom and large closet space. brbrThe outdoor spaces at Oak Point Cottage is captivating. A waterfront that invites play by day, and smores by night. A large lush yard, comprised of wild flowers and large, green spaces. Mature hydrangeas line the deck and the side of the home. There Is a large seaside deck and a gas grill to make the outdoor spaces even more alluring. brbrOak Point Cottage is the perfect place to unwind, relax and enjoy all that midcoast Maine has to offer.
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Exceptional(20)

$1586.84

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Private Vacation Home

Historic Maine Summer Cottage with private beach, 8BR, 3BA

Deer Isle, Maine, United States

The Frederick Law Olmsted Summer Home, also known as Felsted, is a historic house located on the west side of Deer Isle, Maine. It was designed by well-known architect William Ralph Emerson and built in 1896. It was originally the summer home of the landscape architect Frederick Law Olmsted (designer of Central Park in NY). The house is a high-quality example of Shingle style architecture and was listed on the National Register of Historic Places in 1976. Among its many incredible features is that Mr. Emerson placed the house so that you can see the sunset over the ocean and distant islands every day of the year. It is a unique and beautiful property, with stunning views to North Haven, the Camden Hills, and the Eagle Island lighthouse. There are over 600 feet of shoreline along East Penobscot Bay, with Pink granite ledges, and a private beach. The covered porch sits high over the ocean and is the ideal spot to sit peacefully with morning coffee, and to watch the sunset in the evenings.brbrFelsted has been a long-time family home. Your hosts live nearby, and have many years of experience in hospitality and property management. They will do everything they can to make sure you have a wonderful stay. Please read this entire description before requesting a reservation. Thank you!brbrFelsted was a hotel between about 1925 and 1940, and it has been the setting for two movies: Mel Gibson’s 1993 movie “Man Without a Face”, and the 2003 movie “Finding Home”. Felsted has also been featured in numerous books on architecture, including on the cover of Bret Morgan’s recent book: “Summer Houses by the Sea”. It is a wonderful spot for extended family gatherings, and a great place to explore! brbrIn total, there are 8 bedrooms and 3 bathrooms. There are 6 bedrooms on the second floor - two kings, one queen, one bunk bed (double below, twin above), and two twins. One of the 2nd floor twin bedrooms has a trundle bed. There are also two full bathrooms on the 2nd floor. (1 tub/shower combination, and 1 stall shower), and a laundry room. There are two bedrooms on the first floor – one king and one twin with trundle bed, as well as a full bath (1 tub/shower combination). brbrOn the first floor you will find a large eat-in kitchen with gas stove, dishwasher and microwave. There is an elegant wood-paneled living room, dining room and sitting room all overlooking the ocean. brbrFelsted sits on over 4 acres, and has a private beach with beach chairs, hammock, and a picnic table. It is the perfect spot to launch your kayaks, or enjoy swimming and beach combing. brbrFelsted is only a short drive to Stonington, the lobster capital of Maine. You will find everything you need at the property to prepare lobster feasts. brbrFelsted is close to many wonderful activities available on Deer Isle, including Aragosta at Goose Cove, recently named “Best Waterfront Restaurant in Maine” by DownEast Magazine. The Barred Island hiking trail is within walking distance of the house, and there are many other trails on Deer Isle managed by the Island Heritage Trust. Isle au Haut is a beautiful island off the coast of Stonington. It is home to portions of Acadia National Park, and is accessible by ferry from Stonington. In addition, Deer Isle offers many shops, galleries, 44 North Coffee, a farmer’s market, Haystack Mountain School of Crafts, Nervous Nellie’s, and the Deer Isle Granite Museum. brbrAcadia National Park and Bar Harbor are close enough for day trips, whale watches and more!brbrPlease read this paragraph before you request a reservation. In general, Felsted is available to rent from Saturday to Saturday during the summer months but there is some flexibility in the dates. Some reservations are Sunday to Sunday. During other times of year we have more flexibility in the rental schedule. Feel free to write and ask about renting in fall or spring. Felsted is a much loved and lived-in family home. It is 128 years old this year. It is a magnificent historic home, but it does have flaws. We work hard to keep up with the work, but there are some cracks in the old plaster and there are always areas that need some paint. The garage and boat house on the property are not part of the rental. There is internet, but no cable TV and no landline phone. If you have any questions, please write and we are happy to answer!
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Bath 3

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