Holiday houses in Dexter

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Top-rated holiday rentals in Dexter

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Guest favourite
A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.
Cottage in Hermon
4.91 out of 5 average rating, 137 reviews

Lakefront Cottage on Tracy Pond

Lakefront private cottage right on 47 acre Tracy pond. This pond has no public access so it is very quiet with only my home and another Air BnB rental on the 25 acre parcel. 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.

Top Guest favourite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.95 out of 5 average rating, 211 reviews

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

Top Guest favourite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 404 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top Guest favourite
Cabin in Chesterville
5 out of 5 average rating, 161 reviews

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top Guest favourite
The cottage door welcomes visitors with a polished wooden sign that reads 'THE COTTAGE.' Sunlight filters through the glass panel, revealing glimpses of the kitchen interior, where natural light brightens the space and highlights green plants on the windowsill.
Guesthouse in Corinna
5 out of 5 average rating, 17 reviews

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

Top Guest favourite
A hammock is gently suspended between two trees, overlooking Ripley Pond. Lush greenery surrounds the area, creating a peaceful atmosphere. The water's surface reflects the sky, enhancing the sense of tranquility provided by this serene outdoor space.
Cabin in Ripley
5 out of 5 average rating, 71 reviews

Cozy Cabin on the Water in Central Maine with WiFi

Cozy traditional cabin on Ripley Pond right in the middle of Maine. If you are looking for a party scene, this is NOT it. Here you can swim, fish (bass!), paddle, relax by the fire pit or in a hammock or curl up with a good book on the deck or in front of the pretty stone gas fireplace. Fully equipped kitchen makes life easy with gas stove, fridge, microwave and dishwasher. There is a washer and dryer in the bathroom. First floor bedroom sleeps 2, and the loft has 2 futons plus a work space.

Guest favourite
The A-frame chalet features a green metal roof and a wooden exterior, set amidst lush greenery. A small balcony with flower pots is visible on the upper level, while a vintage vehicle is parked nearby on the grass.
Tiny home in Atkinson
4.95 out of 5 average rating, 156 reviews

Cozy Rural A-Frame in the Middle of Maine.

Get away from it all when you stay under the stars. This chalet is right on the ITS trail, nestled in the middle of a small lightly wooded lot in a rural setting. Enjoy the fire pit, bring your snowmobiles, bikes and trailers. The space is cozy with a 55" TV and small kitchen to prepare your meals. The bedroom is in the loft with catwalk opening up to a balcony. Enjoy access to year round outdoor activities as you are nearby Katahdin Iron Works/Jo Mary region and near Sebec and Schoodic lakes

Top Guest favourite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 122 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinme.

Top Guest favourite
A charming two-story home features a light exterior with black shutters. A well-maintained lawn slopes gently in the foreground. Two small steps lead to the front door, flanked by decorative items. Large windows offer ample natural light, while nearby greenery enhances the overall appeal.
Home in Dexter
4.87 out of 5 average rating, 47 reviews

The Belle Air

Bring the whole family to this great place with lots of room for fun. Views of Wassookeag Lake. Walking distance to the public beach and boat landing. Close to ITS 85 trails for ATV's. Walking distance to downtown and Main street shops. Enjoy a sunset on the back porch and a sunrise from the enclosed front porch. Local public golf course less than one mile away. Come relax close to parks restaurants and the great outdoors! 20 minutes from Newport and 1 hour from Greenville.

Guest favourite
A cozy bedroom features a queen bed with white linens, flanked by two nightstands holding lamps. A window allows natural light to enter, showing views of surrounding greenery. Pine wood paneling and a ceiling fan complete the tranquil, modern design.
Home in Dexter
5 out of 5 average rating, 31 reviews

Rail Trail Retreat

Enjoy direct access to the Newport/Dover-Foxcroft Rail Trail from our backyard. Not a rider, enjoy the relaxing cottage feel of our home or venture less than a mile to our “Heart of Maine” small town. Enjoy shops, great eateries and quick lake access for those boaters at the public boat launch. With two bedrooms equipped with queen beds, we also offer extra space in the living room with a daybed & trundle. This home had a complete overhaul in 2022-2023 and is brand new!

Guest favourite
A rustic dining area features a large wooden table surrounded by black chairs. Pendant lights hang from the exposed beam ceiling, illuminating the space. In the background, a fully equipped kitchen is visible, complemented by windows that offer views of the surrounding nature.
Barn in Dover-Foxcroft
4.93 out of 5 average rating, 87 reviews

1890 River Barn

Perched above the Piscataquis River, this historic barn was beautifully renovated into a rustic luxury retreat. Two full stories plus a loft, with relaxing river views on all levels. Gourmet kitchen/dining area with a fireplace & a cozy yet spacious lounge upstairs. Enjoy the garden and patio overlooking the river or unwind in the luxurious copper soaking tub in the loft. Designed for a couple & perfect for romantic getaways, yet comfortable to sleep up to 4 guests.

Top Guest favourite
Home in Abbot
5 out of 5 average rating, 236 reviews

The Lodge on the Piscataquis River is Dog Friendly

Relaxing in the peaceful woods of Northern Maine is the goal here at The Lodge. Our Main Lodge is spacious & beautifully decorated. Perfect for a romantic retreat, family gathering or outings with friends. The beautiful Piscataquis river is located at the back of the property w/ a marked walking path. Enjoy winter & summer activities here like hiking the Borestone..close to Moosehead Lake, Greenville & Monson! ATV, Snowmobile trail access from the house.

Popular amenities for Dexter holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Penobscot County
  5. Dexter