Holiday rentals with outdoor seating in Oakland

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Oakland

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

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Top Guest favourite
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
4.99 out of 5 average rating, 178 reviews

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)

Guest favourite
A modern tiny house is nestled among tall trees, showcasing two large glass walls that allow sunlight to stream inside. The cabin is elevated on stilts, with a snowy landscape surrounding it, creating a serene and private retreat in nature.
Tiny home in Jay
4.93 out of 5 average rating, 266 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Top Guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 203 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top Guest favourite
A cozy living area features knotty-pine walls and a comfortable seating arrangement with a blue sofa. A small coffee table sits atop a textured area rug. A television is positioned on a media console, illuminated by a nearby lamp. Two windows with patterned curtains allow natural light to fill the space.
Home in Farmington
4.98 out of 5 average rating, 244 reviews

Farmington and UMF! Walk to town! Skiers welcomed!

We take great pride in providing a stay that you will remember for years to come. Our moose house is well-stocked with all essential amenities and a few extra surprises! Quaint, convenient neighborhood walking distance to UMF and downtown Farmington. Franklin Memorial Hospital is a short drive. Sugarloaf and Rangeley areas are 45 minutes. WIFI and smart TVs. (No cable.) Washer/Dryer with detergent available. Great place to stay for exploring Maine or a visit with your family and friends.

Top Guest favourite
The open-concept living area features a comfortable couch and a recliner, complemented by a dining table and modern kitchen appliances. Natural light enters through the windows, illuminating the space that is adorned with neutral tones and wood flooring.
Cottage in Augusta
5 out of 5 average rating, 112 reviews

Modern Hideaway in Augusta

Centrally located modern guest home in Augusta, access points to Portland, Midcoast Maine, and Bangor. Spacious master bedroom with closet, additional bedroom, both bedrooms with queen size beds. Handicap bathroom equipped with grab rail and also handicap accessible shower with sit down bench. Many brand new amenities. 55 inch TV has Roku with access to Netflix , Disney Plus, and more! Strong WiFi with the ability to work remotely if needed and explore Augusta and surrounding area.

Top Guest favourite
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
4.86 out of 5 average rating, 220 reviews

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 .

Top Guest favourite
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
4.92 out of 5 average rating, 155 reviews

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!

Top Guest favourite
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
4.91 out of 5 average rating, 106 reviews

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.

Guest favourite
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
4.89 out of 5 average rating, 156 reviews

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.

Top Guest favourite
A dining area is presented with a large wooden table, surrounded by metal chairs. Natural light enters through a nearby window, illuminating the space. A decorative bowl filled with flowers sits at the center of the table, enhancing the inviting atmosphere. Simple wall art complements the decor.
Apartment in Waterville
5 out of 5 average rating, 129 reviews

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

This spacious home of approximately 1,200 square feet is just 1.1 miles from I-95 and located on the ground floor of a charming, two family home completely renovated and tastefully furnished in 2020. Here the “modern design” and “charming rustic feel” mix perfectly. BONUS: Guests have access to the backyard! The private yard boasts a patio set, fire pit, garden, fence and trees along the property line.

Top Guest favourite
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.
Cabin in Freeman Township
4.97 out of 5 average rating, 179 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!

Top Guest favourite
The cabin, with its artistic design, is nestled among trees and features a welcoming entrance path lined with stones. Surrounding foliage contributes to the serene environment, while a scenic view is visible in the distance.
Cabin in New Sharon
4.99 out of 5 average rating, 340 reviews

Kate-Ah-Den Cabin, a soul soothing escape.

Artistically built, cozy cabin on top of Hampshire Hill. Relax, enjoy the breathtaking views, and take time to hear yourself think. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec hiking trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

Popular amenities for Oakland outdoor seating rentals

When is the best time to visit Oakland?

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Avg. price$259 NZD$293 NZD$335 NZD$293 NZD$418 NZD$460 NZD$497 NZD$485 NZD$418 NZD$330 NZD$335 NZD$420 NZD
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Quick stats about holiday rentals with outdoor seating in Oakland

  • Total holiday rentals

    Explore 40 holiday rentals in Oakland

  • Nightly prices starting at

    Oakland holiday rentals start at $167 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Oakland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakland rentals

  • 4.9 Average rating

    Oakland stays are highly rated by guests—averaging 4.9 out of 5!