Vacation rentals with outdoor seating in Oakland

4.99 out of 5 average rating, 174 reviews

The A-Frame cabin is surrounded by tall trees and a snowy landscape, showcasing large windows that reflect warm light. A wraparound deck features outdoor seating, inviting relaxation in a serene wooded setting at dusk.

Cabin in Chesterville

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes

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)

4.98 out of 5 average rating, 209 reviews

A private cottage is surrounded by lush greenery, nestled among trees. The entrance features a wooden deck with two chairs and a small table, inviting relaxation. A well-maintained stone path leads to the cottage, enhancing the private and secluded ambiance.

Cottage in Farmington

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

4.82 out of 5 average rating, 440 reviews

Cabin in Skowhegan

The Cabin -Skowhegan

Main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler. Loft has 2 twin beds. The couch could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large air fry oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/Blue ray player, Gas BBQ (May to November 1st.), as well as a picnic table, out door fire pit. For guest who are traveling by plane, towels are provided, upon request.

4.86 out of 5 average rating, 218 reviews

A spacious living room features a large sectional sofa adorned with colorful cushions. A decorative area rug rests on hardwood flooring, complementing the light walls and artwork. A lamp emits soft light beside the sofa, while a potted plant adds a touch of greenery.

Home in Waterville

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

4.92 out of 5 average rating, 155 reviews

An outdoor soaking tub with a white finish is positioned near the water's edge, surrounded by a gravel area. String lights hang overhead, providing soft illumination. A serene view of the lake is visible, framed by lush trees, as evening twilight casts a calming atmosphere.

Cottage in Sidney

Waterfront Cottage

The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

4.96 out of 5 average rating, 119 reviews

Tiny home in Appleton

Little Apple Cabin on 5 acres, amazing stargazing!

Little Apple Cabin is a private tiny cabin on five wooded acres, created for guests who want quiet, space, and deep rest. Surrounded by trees and farmland, it’s a simple, intentional place to slow down, sleep well, and enjoy Maine without crowds or noise. The cabin features a king bed on the main level, a cozy wood stove, and a wrap-around cedar deck for coffee, reading, and stargazing. Camden and Rockland are about 25 minutes away, and Belfast is about 30 minutes.

4.91 out of 5 average rating, 106 reviews

A scenic lakeside view captures the sunset reflecting on the water, outlining the dock and several boats nearby. The grassy area leads to the water's edge, with trees providing natural framing to the picturesque setting of the Lake House.

Home in Oakland

Lake-House on water, East Lake, Near Waterville

Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

4.98 out of 5 average rating, 183 reviews

A modern kitchen space features metal shelving with glassware and utensils. A stainless steel table holds bowls and a vase of hydrangeas. A door leads to a closet, and a silver trash can is positioned nearby. Artwork is displayed on the wall, adding a touch of character.

Apartment in Waterville

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

4.89 out of 5 average rating, 155 reviews

A corner of the enclosed front porch showcases a wicker chair adorned with a colorful throw blanket. A small, coral-colored table holds a coffee cup, while a potted plant adds a touch of greenery. Natural light streams through the large windows.

Home in Waterville

Sterling House

1960’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as MaineGeneral Thayer Hospital. We are a pet-free home with NO central A/C - fans only. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

4.91 out of 5 average rating, 140 reviews

A spacious living area is showcased, featuring wooden walls and flooring. A cozy couch and an armchair provide seating, while a wooden dining set is positioned nearby. The kitchen area includes essential appliances, with natural light illuminating the space through a door and windows.

Home in Mercer

Moore's place

🇺🇸🏳️‍🌈Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets). Close to hiking, Sugarloaf, ME IT Snowmobile trails is .03 miles away,located between Farmington, Skowhegan, and Augusta If your looking for someone to take you on a hike, and or short kayaking trip, pontoon ride around Lake Wassookeag. moose head lake on a Saturday or Sunday , (with a fee) just let us know

Cabin in Freeman Township

A rustic cabin with a sloped roof is framed by snow-covered trees. Two snowmobiles are parked in front, with a snow-covered pathway leading to the cabin's entrance. Large windows are adorned with light curtains, providing a cozy appearance in the winter landscape.

4.97 out of 5 average rating, 177 reviews

Trailside Cabin

Come & play in the beautiful mountains of western Maine! Cozy, rustic cabin for two. Enjoy miles of multi use trails right off the front steps! If you decide to venture away from the cabin, Rangeley's Saddleback Mt & Sugarloaf USA are both 35 miles away & the college town of Farmington is just 15 minutes south. Our cell service is terrific, but there's no tv or wifi...come to the woods & unplug!

4.99 out of 5 average rating, 237 reviews

A spacious two-story home is showcased amidst a snowy landscape. Snow covers the roof and ground, while evergreen trees flank the entrance. Festive decorations accent the front door, and a gentle snowfall creates a serene atmosphere on the property.

Guest suite in Oakland

Cozy Studio Flat, Belgrade Lakes Region

Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Popular amenities for Oakland outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.99 out of 5 average rating, 105 reviews

The exterior of a charming yellow house is presented, featuring white stairs leading to a green front door with an ornamental design. Lush shrubs frame the entrance, and tall trees provide shade to the vicinity, creating a welcoming appearance.

Home in Waldoboro

1830s Cape hosted by George & Paul

4.9 out of 5 average rating, 238 reviews

The exterior of the house is depicted, featuring a charming blue and gray facade. Vibrant pink flowers line the front, and a well-maintained lawn is visible, adding a touch of greenery. The porch displays planters, creating an inviting entrance to the home.

Home in Buckfield

The Nifty Village House

4.94 out of 5 average rating, 230 reviews

A serene view of Wilson Pond is presented, bordered by lush greenery and rolling hills. The lake reflects the blue sky and scattered clouds, creating a peaceful natural landscape. The surrounding trees provide a rich frame, highlighting the tranquil waters.

Home in Wayne

Peaceful Getaway at The Ledges

4.95 out of 5 average rating, 111 reviews

The exterior of the house features a charming gray shingle facade with white trim, complemented by blooming purple azalea bushes. A neatly paved driveway leads to the entrance, while green grass surrounds the base of the structure and tall evergreen trees provide a natural backdrop.

Home in Rockport

Seaside House/Upstairs

Superhost

The inviting living area features a stone fireplace with a mirror above it, surrounded by plants and wooden beams overhead. A wooden staircase leads to the upper level, while a dining area with several chairs is visible in the background, enhancing the warm and cozy ambiance.

Home in New Portland

4.86 out of 5 average rating, 160 reviews

The Riverfront Retreat - 27 minutes to Sugarloaf!

4.96 out of 5 average rating, 193 reviews

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

Lakefront: Private Hot Tub, Sauna & Free Massages!

4.99 out of 5 average rating, 167 reviews

The exterior of a cozy lake house is shown, surrounded by tall, snow-covered trees. A blanket of fresh snow covers the ground, with clear pathways leading to the entrance. Large windows reflect the soft winter light, adding a serene ambiance to the scene.

Home in Canton

Private Lake House, Firepit & Amazing Sunset Views

4.88 out of 5 average rating, 101 reviews

A comfortable living area features a green sofa paired with a rustic wooden coffee table. Sunlight streams through two large windows, illuminating the light-colored walls and warm wooden floors. An air conditioning unit is mounted on the ceiling, and there is a cozy armchair in the corner.

Home in Liberty

Modern Lakefront Home w/ Hot Tub • Winter Escape

Apartment rentals with outdoor seating

4.84 out of 5 average rating, 181 reviews

The exterior of a two-story building is shown, featuring beige siding and dark wood doors. Flower pots are placed near the entrance, and a parking area is visible in front. Nearby structures and greenery are seen in the background, suggesting a quaint neighborhood.

Apartment in Hallowell

3 bed up apt with no cleaning fee or checklist

Apartment in Damariscotta

The living area features bright yellow walls and ample natural light from multiple windows. A round table with floral tablecloth sits center stage, surrounded by chairs. Two couches, one textured and the other a neutral tone, are positioned near the walls adorned with artwork.

4.92 out of 5 average rating, 299 reviews

Fernald's Backside

4.96 out of 5 average rating, 116 reviews

A charming three-story house is surrounded by lush greenery and colorful flowering shrubs. The white exterior features multiple windows and a prominent roof. A pathway leads to the entrance, with a lamppost adding a classic touch to the inviting front yard.

Apartment in Pittsfield

The Retro 2 bedroom

4.95 out of 5 average rating, 116 reviews

An entryway features a blend of natural light and neutral tones. A wooden sideboard and a blue chair provide seating, while a decorative rug adds warmth. Potted plants enhance the aesthetic, and a doorway leads into a spacious living area, subtly defined by a contrasting color scheme.

Apartment in Wiscasset

25 MIDDLE -Historic Village Apartment (Unit A)

5 out of 5 average rating, 103 reviews

A bright entryway features a light-colored door flanked by windows. A simple staircase leads to the second floor, while a small hall opens to the kitchen area. Natural materials are incorporated through woven basket and striped textiles hanging on hooks.

Apartment in Rockland

Coastal, relaxing, light-filled + walkable

4.97 out of 5 average rating, 317 reviews

An open living area features a dining table surrounded by black metal chairs, with a cozy sofa nearby. Large windows allow natural light to fill the space, showcasing green walls and a neutral rug. Decorative elements add character without overwhelming the tranquil ambiance.

Apartment in Rockport

The perfect getaway - Camden/Rockport/Rockland

Apartment in Damariscotta

A spacious living area features a blue sofa with decorative pillows, a wooden rocking chair, and a coffee table atop a patterned rug. A TV and shelving unit are present, along with a white chair and a lamp, creating a comfortable and functional space.

4.97 out of 5 average rating, 103 reviews

The Gallery Apartment

Apartment in Damariscotta

A bright interior is seen with natural light streaming through multiple windows. A cozy seating area features a small dining table and four white chairs, while a granite countertop kitchen is visible in the background. A television is mounted on the wall, enhancing the space's functionality.

4.99 out of 5 average rating, 108 reviews

Midcoast In-Town Retreat

Condo rentals with outdoor seating

An open-concept living space features a comfortable leather sofa and armchair, with a coffee table at the center. A dining table with white chairs is positioned nearby, while a well-equipped kitchen displays stainless steel appliances. Bright light fills the room through multiple windows.

4.66 out of 5 average rating, 83 reviews

1BR water-view condo with deck & WiFi

The exterior of the two-bedroom condo is presented, showcasing a gray shingle facade and a well-maintained lawn. A stone pathway leads to the individual entries, each featuring a small porch. Lush greenery surrounds the building, enhancing the tranquil ambiance of the setting.

4.72 out of 5 average rating, 79 reviews

Stylish 2BR | Balcony | River Views

A scenic view of Sheepscot River is framed by tall trees and lush greenery. The landscape features a mix of pines and shrubs, with the river visible in the distance, enhancing the natural beauty of the surroundings.

4.53 out of 5 average rating, 49 reviews

1BR | Water Views | Deck | Full Kitchen

An open-concept living area features a comfortable sofa and an armchair that provide seating for four. A dining table is positioned nearby. A flat-screen TV is mounted on the wall, and large doors lead out to a deck, offering natural light.

4.55 out of 5 average rating, 49 reviews

1BR Waterview | Deck | Partial AC

5 out of 5 average rating, 83 reviews

The living area features two inviting sofas positioned around a central coffee table. A flat-screen TV is mounted on the wall, and natural light filters through two windows. A lamp adds a touch of warmth to the space, complemented by tasteful decor.

Condo in Oakland

Home away from home cozy new Apartment in Oakland

A serene waterfront scene captures a dock curving toward a hazy sunrise over the water. Soft clouds scatter in the sky, reflecting gentle hues of orange and yellow, while a bridge is visible in the distance. Green grass and reeds frame the tranquil setting.