Holiday rentals in Dexter

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Top-rated holiday rentals in Dexter

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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, 223 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 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.
Guest house in Corinna
5 out of 5 average rating, 18 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
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, 136 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Top guest favourite
The exterior of Moosepines Lodge is depicted, featuring a large, welcoming porch shaded by a roof with exposed beams. The entrance is adorned with seasonal decorations, while a picnic table and benches provide seating. Surrounding pine trees create a serene woodland atmosphere.
Home in Abbot
5 out of 5 average rating, 237 reviews

Piscataquis River Lodge is Dog Friendly

SNOWMOBILE ACCESS FROM PISCATAQUIS RIVER LODGE! 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. Surrounded by many hiking trails and close to Moosehead Lake, Greenville & Monson! Direct ATV and Snowmobile trail access from the lodge

Guest favourite
A historic covered bridge is depicted, nestled in a snowy landscape. Tall trees with bare branches frame the image, while a gentle river flows beneath the bridge, partially frozen. The bright blue sky enhances the serene winter scene.
Flat in Sangerville
4.84 out of 5 average rating, 195 reviews

Rustic Country Apartment on The Moosehead Trail.

We recently acquired the house we live in which has an efficiency apartment in the back. It is cozy and private. The house is old and unique. It was previously a long term rental. We wanted to provide a restful space in the heart of Maine Highlands, the crossroads of Central Maine. We enjoy the scenic area with beautiful lakes rivers, multiuse trail systems and trail head of the 100 mile wilderness of the Appalachian Trail, Moosehead lake, Maine's largest lake, and State Parks.

Top guest favourite
A rustic wooden sign welcomes visitors at the entrance, featuring carved letters. The scenic property is framed by greenery, with a spacious gravel area and a large wooden garage on the left. The lodge building stands in the background, surrounded by trees and open sky.
Cabin in Milo
4.96 out of 5 average rating, 166 reviews

Maine Lodge & Cabin getaway

Muk-Bog Lodge is settled on 30 acres of Maine woods and surrounded by more than 100 acres of preserved Maine woodlands. Located on a private drive several hundred yards from the main roadway, this Lodge offers you privacy while still being within 10 minutes of downtown Milo. The Lodge also offers a 30x40 garage for storage or parking while renting. There is also a 12x14 mudroom at the entrance for more storage and a open 12x12 back deck overlooking the firepit and back lawn area.

Guest favourite
Tiny home in Bangor
4.85 out of 5 average rating, 149 reviews

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.

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.

Top 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, 36 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
The kitchen features light-colored cabinetry and a large island with seating for four. A spiral staircase is visible, leading to the upper levels. Natural light is provided by windows above the sink and in the dining area, which includes a wooden table and chairs.
Flat in Pittsfield
4.89 out of 5 average rating, 117 reviews

Loft Retreat

Welcome to our enchanting loft retreat! Our thoughtfully designed apartment offers a serene escape with a touch of sophistication. Ascend the spiral staircase to discover a cozy bedroom complete with a work space and reading nook. Hidden up a trap door on the third level are two twin beds for the nimble. A full deck complete with a small fire pit is available in the warmer months. Your getaway awaits!

Guest favourite
A quaint exterior of the carriage house is presented, featuring a porch with railings and two chairs. Lush green grass surrounds the house, complemented by mature trees offering shade. The sky is bright blue, bringing a cheerful atmosphere to the setting.
Guest house in Dexter
4.88 out of 5 average rating, 111 reviews

The Carriage House at Peony Hill

Come stay on the grounds of a 1913 French Colonial in the original carriage house at Peony Hill. The carriage house is a full one bedroom, full bath, kitchen, eat-in dining area, along with spacious living room complete with a cottage/cabin feel. The new June 2022 remodel decor is quaintly appointed with regional Maine finds and vintage antiques scattered in the professional decor.

Top guest favourite
A light-filled sitting area features a gray sectional sofa adorned with decorative pillows. A cozy throw blanket is draped over the armrest. A round pouf rests on the patterned rug, while a small side table sits beside the couch. A wall-mounted TV and potted plant add to the space.
Cottage in Hampden
4.98 out of 5 average rating, 331 reviews

MaineStay Cottage #5 Full Kitchen Hampden/Bangor

Welcome to MaineStay Cottage #5 highlighting a bright and airy living space with unique Maine touches throughout. Featuring a remodeled fully stocked kitchen, an electric fireplace, a smart TV for streaming your favorite shows, with a charming dining area for 2, a comfortable queen size bed, and everything you’d need for a relaxing stay - you can’t go wrong!

Popular amenities for Dexter holiday rentals

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