Hotel holiday rentals in Chester

Hotel room in Island Falls

A cozy room features a spacious bed dressed in a floral blanket, complemented by a green accent wall. A plush armchair sits nearby, and natural light illuminates the space. A doorway leads to the kitchenette area, enhancing the room's functionality.

4.88 out of 5 average rating, 104 reviews

Private Queen Room W/Kitchen In 1894 Opera House!

Please read check-in instructions—parking, key access & arrival tips are included for a smooth arrival. We suggest researching the area ahead to know what’s nearby and come prepared, as we aren’t always instantly available to reply. Direct ATV/snowmobile trail access with trailer parking. On-site Pub Lounge: Thurs 4–8, Fri 4–10, Sat 12–10 with food, drinks & events. Some sound may carry—no complaints so far, but please don’t book if that may be an issue. Ask about private 1920s theater time! 🎬

A comfortable private room is highlighted by a queen size bed covered with a light grey quilt. A small table with a desk lamp is positioned nearby. Fresh towels are neatly arranged on the bed. The ensuite bathroom is visible in the background.

4.97 out of 5 average rating, 38 reviews

Freedom House Cottage Room #3

This is a quiet and quaint private room with a queen size bed and ensuite bathroom in our Cottage Building. A mini-fridge, microwave, coffee maker, WiFi, and cable TV are provided in the room for your comfort. Our entire facility is SMOKE FREE! We are located in downtown Dover-Foxcroft within walking distance to shops, cinema, restaurants, bank, post office & drug store. A full breakfast is available for an added charge of 20.00/person, but must be requested at least 24 hrs prior to arrival.

A bright studio space features a plush king-sized bed and large windows with views of the street. A walnut wall desk and stylish chair are positioned against one side, while a cozy orange chair adds a pop of color. Dark curtains frame the windows.

4.87 out of 5 average rating, 123 reviews

Heart of Downtown | Historic Hotel | Fast WiFi

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!

A spacious bedroom features a king-sized bed dressed in soft linens. A wooden nightstand with a marble top and a wall-mounted shelf are visible, alongside a dresser. Natural light brightens the room, creating a calm and neutral atmosphere.

4.8 out of 5 average rating, 236 reviews

King Bed|Historic Hotel Bangor

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: ☀ 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!

A spacious bedroom features a king-sized bed with white linens, complemented by large windows offering views of the city. A modern TV is mounted on the wall, alongside a sleek desk with refreshment options. Natural light enhances the light wood flooring.

4.91 out of 5 average rating, 108 reviews

Historic Building|DTWN Bangor*King Bed*FAST Wi-Fi

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 Airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ King-sized bed ☀ Premium front Market Square View ☀ 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!

A spacious guest room features exposed brick walls and wooden beams. Two distinct sleeping areas are arranged with a bed and a pull-out couch, complemented by decorative oars on the wall. Natural light streams in through large windows with simple shades, illuminating the modern furnishings.

4.68 out of 5 average rating, 22 reviews

The Mill Inn: Rm 3, 2 Queens w/ Partial River View

The Mill Inn is a boutique hotel in a renovated mill located in the heart of Dover-Foxcroft, Maine. Room three is a second floor room with two queen beds offering partial river views accented by charming decor with a nod to Maine culture. The Mill is a 60,000 square foot historic mill complex that was renovated in 2015 into a mixed-use building with residences, office space, and a boutique inn. While closed during Covid, the Mill Inn reopened in the fall of 2021 under new management.

A bright room features a plush bed with white linens positioned under two large windows adorned with dark curtains. A flat-screen TV is mounted on the wall, while a comfortable armchair and a wooden dresser complement the inviting space.

4.89 out of 5 average rating, 190 reviews

Historic Hotel|Heart of Bangor|Fiber Wi-Fi|Roku TV

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 airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ Plush Queen-sized bed w/ high end Centium Satin linens ☀ High Speed Internet ☀ 50” Roku TV w/ HULU + ☀ Desk ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

The spacious room features wood floors and two distinct sleeping areas. A large bed is dressed with a neutral-toned coverlet, while a smaller bed sits in the corner. Natural light enters through a nearby window. A dining table with chairs is also visible.

5 out of 5 average rating, 6 reviews

Unit 21: One King Bed & One Twin, Second floor

This newly renovated unit is GORGEOUS! Features it’s own private entrance and second story porch with patio seating. Beautiful French doors. Comes with full size fridge with microwave and coffee maker! Also comes with a cute table and two antique chairs. Two windows for sunlight. Equipped with Wi-Fi and also Roku, for your streaming entertainment. Features a half bathroom with beautiful brand new tiled shower. Wood floors, this room is just like home!

A spacious hotel room is furnished with two queen beds dressed in neutral bedding. A small dining table with chairs occupies one corner, while a mini fridge, microwave, and coffee maker are arranged on a side counter. A window provides natural light, with a door leading to a porch.

Hotel room in Abbot

5 out of 5 average rating, 5 reviews

Abbot Trailside Hotel Style Room

Hotel Style Room with 2 queen beds, full bath, table/chairs, mini fridge, microwave, coffee maker, and covered porch. We're located in a peaceful county setting, off the beaten path. We have direct ATV & Snowmobile trail access, and plenty of parking for trucks/trailers.

Hotel room in Millinocket

Katahdin Room at the Appalachian Trail Hostel

Kick back in a queen bed in this picturesque room as you explore the Katahdin region. Fitted with original trail signs from the mountain and a beautiful portrait of Katahdin, you’ll experience comfort in your home away from home.

4.72 out of 5 average rating, 39 reviews

A view from the porch showcases the exterior of the motel, with several rooms lined along a gravel pathway. A vibrant mix of autumn foliage is visible among the trees, and a flag is seen in the foreground, adding a welcoming touch.

Hotel room in Medway

Maine, the way life should be

We are a 10 room motel on the west branch of the Penobscot River in Medway Me. The atv trail and Snowmobile trail its83 runs through our property, with plenty of parking. We offer rooms with 1 Queen bed or 2 double beds.

5 out of 5 average rating, 17 reviews

A spacious guest room features two queen beds dressed in neutral bedding, providing a comfortable sleeping area. A small sitting area with a chair is seen, along with a work desk equipped with a chair and a television mounted on the wall. Natural light enters through a window dressed with a sheer curtain.

Hotel room in Orono

Modern Campus Retreat w/ Unique Coburn Hall Rooms

Located inside UMaine - Orono, steps away from its facilities. Embrace campus life at our doorstep and discover Orono's charm—perfect for UMaine visits, arts, and scenic trails. Enjoy Maine's essence with us!

Popular amenities for hotel rentals in Chester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly hotel rentals

A well-lit room is furnished with two queen beds, each adorned with decorative pillows. A wooden nightstand is located between the beds. Natural light enters through two windows, which are dressed with light curtains. A chandelier hangs from the ceiling, accentuating the cozy atmosphere.

Unit 15: Two Queen Beds

A queen bed is positioned centrally in a room with warm-toned curtains framing large windows. Two bedside lamps provide soft illumination, and a decorative pillow adds an accent to the bed's neutral linens. A small side table is visible next to one lamp.

3.75 out of 5 average rating, 4 reviews

Unit 12: One Queen Bed

A rustic wooden desk is positioned against a wall, accompanied by a black stool. A small potted plant and a decorative basket filled with snacks sit atop the desk, while large windows allow natural light to illuminate the space.

4.6 out of 5 average rating, 5 reviews

The Mill Inn: Room 4, Main St. & River View King

Private room in Millinocket

100 Mile Wilderness Room at the AT Hostel

Private room in Millinocket

Nimblewill Room at the Appalachian Trail Hostel

A spacious bedroom features a king-sized bed with a dark comforter and multiple pillows, accompanied by a bedside lamp and a small side table. A rustic chandelier hangs above, illuminating the room. A dining table is positioned near a door with a partially draped window.

5 out of 5 average rating, 4 reviews

Unit 17: One King Bed

A spacious guest room features a king bed with a light-colored duvet and a decorative pillow. A bedside lamp stands on a nightstand, while a 55-inch TV is mounted on the wall opposite. A large window allows natural light to fill the space.

Hotel room in Orono

New Open Stay inside UMaine! On-site Dining, Park

Private room in Millinocket

Earl Shaffer Room at the Appalachian Trail Hostel

Hotel rentals with a patio

A cozy sleeping area features a spacious bed covered with a textured gray bedspread. A small decorative pillow adds a touch of color. Natural light enters through the nearby door, and a framed floral artwork decorates the wall above the bed. A lamp stands next to the bed on a side table.

Unit 26: One Queen Bed

A cozy room features two queen size beds, accented by soft linens and decorative pillows. A small dining table with chairs and a lamp provide a functional space. Natural light filters through the curtains, illuminating the muted color palette. A flat-screen TV is mounted on the wall.

Unit 10: Two Queen Beds

A spacious bedroom with a king bed draped in a textured quilt offers comfortable accommodations. Two lamps sit on either side of the bed, while large windows dressed with sheer curtains allow natural light to fill the room. The sloped ceiling adds architectural interest.

Unit 14: King Bed

A cozy room features two queen beds covered in a subtle quilted pattern. A wall-mounted television is positioned across from a small table and chairs. An apartment-sized refrigerator and microwave are visible next to the sliding door, while natural light filters through a curtain-covered window.

Unit 27: Two Queen Beds

Other hotel holiday rentals

A custom reclaimed wood desk is paired with a circular black stool, positioned under a wall-mounted artwork. A small plant, a notepad, a lamp, and a water bottle are placed on the desk. Exposed brick can be seen in the background, enhancing the room's character.

Hotel room in Millinocket

The Mill Inn: Rm 6, Corner Room w/ Main St. View

The exterior of Pamola Motor Lodge is presented, showcasing a two-story building with multiple balconies. A welcoming entrance features a covered porch, and a clear parking area is visible in front of the lodge. The surrounding landscape includes ample space for vehicles.

Mountain Escape: Pamola Lodge by Baxter State park

The spacious guestroom features a king-size bed with a striped comforter and a twin daybed with a trundle. Natural light fills the room through two windows, with a small rug positioned on the polished wooden floor. A mirror and bedside lamp add functionality.

Hotel room in Dexter

The Clifton Room at The Brewster Inn B&B

A spacious common area is highlighted by wooden walls and a warm ambiance. Comfortable seating includes two armchairs and a long bench, while a rustic table with chess pieces invites casual games. A cozy fireplace is centrally positioned, enhanced by natural light from the windows.

Hotel room in Dexter

The Game Room at The Brewster Inn B&B

An interior view showcases warm wooden beams and exposed brick walls. A spacious bed is centered in the room, accompanied by colorful decorative pillows. Vintage-style wall decor, including red-painted paddle and hanging items, complements the light streaming through large windows.