Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
A hand holds a cup labeled 'Maine' against a backdrop of shimmering water reflecting vibrant autumn foliage. The still water is bordered by large rocks and trees, enhancing the serene atmosphere.
Cabin in Burlington
4.95 out of 5 average rating, 202 reviews

Secluded Waterfront Cabin

Please Message me to ask about possible discounts and length of stay minimums. Secluded four season cabin is located on remote Saponac Lake in Burlington, Maine. Last camp on a private dead end road with clear views of the lake. Perfect location for fishing, kayaking, or just relaxing in a hammock. Fully furnished with A Minisplit Heat Pump/ AC, and Propane "wood stove" well water, and high speed WiFi. Within 30 minutes of Lincoln and 1 hr of Bangor. Both towns have shopping, restaurants,etc.

Top guest favourite
A cozy camp is surrounded by tall trees, showcasing a classic A-frame roof and a porch with seating. The white exterior is complemented by green trim, while areas of orange pine needles cover the ground. The setting reflects a serene, natural atmosphere.
Cottage in Brownville
4.98 out of 5 average rating, 113 reviews

Sled/Ice Fish/Perfect Lakeside Getaway!

The perfect lakeside getaway spot with beautiful views. It is renovated with an old time cozy camp feel, with modern conveniences. This pet friendly camp is across the street from Schoodic Lake. The cozy camp sleeps 5-6 comfortably with on-site parking for three. The camp is located on ITS 111 trails for snowmobiling and ATVing. Hunting, fishing and hiking destinations include, Baxter State Park, Gulf Hagas, and Katadin Iron Works. Water access at Knights Landing just a short distance away.

Top guest favourite
A cabin interior showcases a welcoming open layout with wooden walls and a cozy atmosphere. Comfortable seating is provided by leather sofas and a recliner. A wooden coffee table sits in the center, and the kitchen area, visible in the background, features wood cabinets and modern appliances.
Cabin in Enfield
4.97 out of 5 average rating, 116 reviews

28 Holiday Lane Beach Front Cabin

4-Season Cabin next to Morgan's Beach on beautiful Cold Stream Pond rented year round. This is the perfect location for a family vacation or business/working people who travel and have temporary assignments lasting one week to several months. Cabins are fully furnished and include: heat, hot water, electricity, Direct TV, WiFi, trash removal, driveway and roadway plowing. Cabins are 10 minutes to Penobscot Valley Hospital in Lincoln and 40 minutes to EMMC in Bangor. Weekly & Monthly Rates.

Superhost
A spacious room features a king-sized bed adorned with smooth linens. Elegant drapes frame the windows, allowing natural light to fill the space. An entertainment area is visible, showcasing a mini fridge and coffee maker, with tasteful décor enhancing the modern design.
Flat in Bangor
4.88 out of 5 average rating, 167 reviews

King Bed|DTWN Historic Hotel|Fiber Wifi|50"Roku

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* 3 mi. to airport 43 mi. to Acadia National Park 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ King-sized bed w/ high end Centium Satin linens ☀ High Speed Fiber Internet ☀ 50” Roku TV w/ HULU + ☀ Work space ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

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.

Superhost
A cozy living area features a dark sofa complemented by plush cushions, flanked by two comfortable armchairs. A low coffee table stands atop a soft area rug, while natural light streams through two windows, providing a bright and inviting atmosphere.
Flat in Millinocket
4.77 out of 5 average rating, 116 reviews

"The Last Hike" Downtown Millinocket

PLEASE READ ALL THE DETAILS OF OUR LISTING. 3rd floor, converted attic "Penthouse" apartment is steps away from Downtown Millinocket and all your outside adventures: fishing, snowmobiling, skiing, white water rafting, biking, etc. Close access to snowmobile trails, 2 minute walk to downtown/Marathon, close to Katahdin and Baxter State Park. Can't promise you will see a rainbow out our window, but on a clear day, when the leaves have fallen off the trees, you can see Katahdin!

Top guest favourite
The kitchen features a central island with seating for two, highlighted by a pendant light overhead. Equipped appliances include a microwave, coffee maker, and a stove. Colorful patterned curtains frame the window, adding a touch of charm to the functional space.
Flat in Millinocket
4.92 out of 5 average rating, 416 reviews

Near Downtown Apartment

Two bedroom second floor apartment! Chalkboard wall, (with art and signatures from guests all over the world since 2018 dont forget to sign the wall) two tv’s (master bedroom and LR) with Netflix, Hulu, + access, and high speed internet! Owner occupied building. Street next to downtown, hiking trails, and snowmobile trails! We are not near a lake, no idea why airbnb did that and can not change it. We are near a river that many take kayaks and canoes out onto.

Guest favourite
A well-equipped kitchen features a stove with a clean black surface and utensils arranged nearby. Large windows provide a view of the lake and surrounding trees, allowing natural light to fill the space.
Cabin in Lincoln
4.9 out of 5 average rating, 77 reviews

Private dock, king beds, screened in porch, AC.

Cozy lake front cabin with two king bedrooms + twin bunk room. Heat pump for warmth and/or cooling. Screened in porch overlooking the lake with table for dining or playing games on a rainy day, a lakeside fire pit, private dock, and large deck with grill. Come swim, fish, kayak/canoe, relax, and listen to the loons call! 10min from I-95 and town, restaurants, and grocery store. **Dock is in the water seasonally generally June- mid September.

Guest favourite
A serene lakeside view features a grassy area leading to Cambolasse Pond. A stack of firewood stands neatly beside the water's edge, while a small boat is visible on the calm lake. Lush trees and a clear blue sky complete the peaceful setting.
Cottage in Lincoln
4.76 out of 5 average rating, 76 reviews

Home with Sandy Beach On Cambolasse Pond

Welcome to Lincoln! This Camp is Located on a beautiful 1.3 acre flat lot with ample parking, sandy beach, shallow lake access and the ability to launch your own boat right from shore! Excellent snowmobiling,swimming, boating and fishing. Located on Cambolasse Pond there is not many like this. Private pond, Very peaceful Comes with sheets, pillows, and some towels. I recommend bringing extra towels and any other essentials you may need.

Guest favourite
The cabin's exterior features a rustic wooden facade with large windows framed by greenery. A small front porch with steps leads to the entrance. A gas grill is situated nearby, set against the backdrop of surrounding trees and open grass.
Cabin in Wytopitlock
4.88 out of 5 average rating, 163 reviews

Birch hill camp

Modern cabin w/power, water. 3 bunk beds in one large bedroom,sleeps 6. Outside firepit. Miles of woods via logging roads to explore moose, deer, bird watching, hunting. Fishing for trout bass/perch. Guided hunting, fishing, and canoeing available, ponds and rivers. Canoes maybe available. X skiing and snowshoeing Trail from camp to ITS snowmobile trail 1/2 mile. Bed linen/light blanket provided. Towels not provided

Guest favourite
The cabin is featured with a warm red exterior, complemented by white trim and a welcoming front door. Surrounded by tall trees and a natural landscape, a decorative sign is positioned near the entrance, enhancing the inviting appeal of the property.
Home in Lincoln
4.9 out of 5 average rating, 63 reviews

Cozy and Quiet Waterfront Cottage in Lincoln Maine

Breathtaking views! Pets welcome! Beautiful private waterfront cabin located on Caribou Pond in Lincoln Maine. Enjoy a peaceful getaway in the great outdoors with all Maine has to offer every season. ATV/Snowmobile trails close by, ice fishing, ski resorts, and so much more. The town of Lincoln with shopping and restaurants is 10 mins away, Bangor is 45 minutes south and Katahdin region is less then an hour north.

Popular amenities for Chester holiday rentals

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