Holiday rentals with outdoor seating in Chester

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Chester

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern post and beam house is set against a backdrop of trees. The exterior features large glass windows that enhance natural light. A spacious deck with railing is visible, providing an outdoor space for relaxation.
Home in Millinocket
4.98 out of 5 average rating, 116 reviews

Rice Farm Hideaway; A little slice of heaven.

This sweet post & beam house is located near town yet private and tucked away in the woods, cozy & comfortable, pet friendly, close to ATV & snowmobile trails, and Baxter State Park, Katadhin Woods and Water, plus numerous lakes and the beautiful Penobscot River. The house can comfortably sleep up to 6 people. The living area is open and sunny with a big kitchen. There is plenty of parking for recreational trailers. Come enjoy a rewarding climb up Katahdin or grab a book and read on the deck.

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
4.94 out of 5 average rating, 233 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
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, 148 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
A houseboat floats gently on the calm waters of Lake Pemaquid, surrounded by lush greenery on the hillsides. The vessel features large windows, a spacious deck, and a vibrant red and cream exterior, reflecting the tranquil ambiance of the natural setting.
Boat in Lakeville
5 out of 5 average rating, 116 reviews

Houseboat ROAM in Lakeville, Maine

- A Little Closer To Nowhere - A one-of-a-kind eco-travel experience, ROAM is a simple - but comfortably equipped - houseboat that can accommodate two guests. Homeported on Junior Lake in Lakeville, Maine, you will seamlessly integrate into your surroundings while enjoying visiting loons, sweeping sunsets, and clear northern air. Bathroom and full kitchen aboard. ROAM is operated off of Wild Fox Cabins - please inquire if you'd like to add land options or hire a local hunting or fishing guide!

Top Guest favourite
A wooden dock extends out over tranquil waters, flanked by lush greenery. The water's surface reflects the calm sky, creating a serene atmosphere. Steps lead down from the dock to the gently lapping water, inviting relaxation and aquatic activities.
Cottage in Glenburn
4.95 out of 5 average rating, 249 reviews

Your own private getaway on Pushaw Lake!

Welcome to Pushaw Lake! You’ll find all the comforts of home here! :-) Come for the weekend! Save 20% for a week, or 30% for a month stay! :-) Jump in the lake or go on an adventure in a kayak or canoe this summer! Bring snowmobiles, snowshoes, skis, or go ice-fishing this winter! :-) Relax... Read a book and listen to the Loons, or sit around the fire pit and say goodbye to stress! :-) You’re less than 20 minutes from Bangor International Airport, Downtown Bangor, and UMO! :-)

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, 119 reviews

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 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, 205 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 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, 117 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.

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, 157 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

Guest favourite
The interior of the custom-built yurt features a high, circular ceiling with a skylight at its center. A modern kitchen with stainless steel appliances is visible, alongside a spacious countertop. A loft area is accessed by a wooden staircase, with wooden beams and walls enhancing the natural aesthetic.
Yurt in Medway
4.95 out of 5 average rating, 167 reviews

Katahdin Riverfront Yurt

Glamping at its best! Beautiful custom built yurt on the banks of the Penobscot river along the Grindstone Scenic Byway. Close to Baxter State Park and majestic Mount Katahdin as well as Katahdin Woods and Waters National Park. Two miles to Penobscot River Trails with miles of groomed cross country skiing and mountain biking. 4 seasons of hiking, biking, fishing, canoeing, kayaking, white water rafting, skiing, and miles and miles of snowmobiling! 1 hour to Bangor 2 hours to Bar Harbor

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.

Top Guest favourite
A lakeside cabin is framed by lush green trees, showcasing a wooden dock that extends over calm waters. The structure features large windows and a deck with outdoor seating, providing a serene view of the lake and surrounding nature.
Cabin in Hudson
4.9 out of 5 average rating, 123 reviews

Waterfront| Fire pit| Deck|Kayaks

Come and make lifelong memories at The Eagles Nest on Beautiful Pushaw Lake! Newly renovated loft provides a unique camping like experience for children...or allows Adults to revisit their inner child. -Explore the lake with the one tandem and 2 child kayaks provided -Enjoy Barbecuing with our 4 burner grill on the outside deck just feet from the waters edge -Take a swim or relax with a good novel on the outside Hammock -Many family friendly nearby trails to hike and snowshoe

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