
Holiday rentals with outdoor seating in Oakland
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
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 $144 AUD per night before taxes and fees

Verified guest reviews
Over 1,440 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!
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.

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks
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- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Maybelle the Tiny Cabin on 100 acres
Maybelle is an 8x18 cabin with a full-size loft bed, a Cubic Mini Woodstove (wood provided), Natures Head Composting Toilet and Jetsetter massaging hot tub. Kayaks, paddle board, & canoe included . Hiking trails (some solar lit) surround your cabin. Outside is a fire pit and a quick path to the water. Maybelle's kitchen has all the cooking essentials and there's a small propane grill outside & the fire pit for cooking. Cell reception is okay in the cabin, wifi is from a Starlink booster!

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!

Brook Ridge Retreat
Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Secluded Retreat w/ Luxe Hot Tub & Forest Views
Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

Sunset Chalet Lakefront Hot Tub Game Room
Tucked along the peaceful shore of Belgrade Stream, Sunset Chalet is a private, waterfront escape designed for cozy connection and quiet joy. With a hot tub beneath the trees, a warm fire flickering inside, and a playful game room downstairs, it’s the perfect space to unwind and make memories. Whether you’re celebrating a honeymoon, anniversary, or enjoying a relaxed family getaway, Sunset Chalet offers a setting that feels both special and deeply comforting.

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.

Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

SNOW SWEET, A Yurt for All Seasons
Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

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.

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.

Cozy Rock Cabin #thewaylifeshouldbe
*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!
Popular amenities for Oakland outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Kirby Island Road Retreat

Stunning Mountain & Ocean Post&Beam

Sterling House

Hallowell Hilltop Home

Peaceful Getaway at The Ledges

Riverside

Lakefront: Private Hot Tub, Sauna & Free Massages!

Farm house, River, Island, animals & private Chef.
Apartment rentals with outdoor seating

Sweet Retreat: 2 BDR Home Mins to Colby

25 Middle: Two floor loft w. water view -sleeps 5

Downtown Hideaway-Loft HotTub Modern Clean Private

The perfect getaway - Camden/Rockport/Rockland

Sunny In-Town Camden Studio, 10% weekly discount

A Home away from Home.

The Heron's Nest Cozy apartment in the woods.

Welcome to "West Winds at Pemaquid"
Condo rentals with outdoor seating

Studio Condo, Mountain Views Avail For The Summer!

Family Condo 5 min to Sugarloaf

Mabel's Maine Studio on the River

Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony

Waterviews|Sunsets|Boothbay Harbor

Cozy Ski-In/Ski-Out Escape at Sugarloaf with AC

Harbor View Cottage Unit A 2 bedroom downtown

Truly ski in/ski out. Studio near the Super Quad .
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $409 AUD | $409 AUD | $351 AUD | $252 AUD | $360 AUD | $396 AUD | $428 AUD | $418 AUD | $360 AUD | $284 AUD | $288 AUD | $362 AUD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Bar Harbor Holiday rentals
- Salem Holiday rentals
- New Haven Holiday rentals
- Rentals with a washing machine and dryer Oakland
- Pet-friendly rentals Oakland
- Rentals with a kayak Oakland
- House rentals Oakland
- Waterfront rentals Oakland
- Cabin rentals Oakland
- Family-friendly rentals Oakland
- Rentals with a fireplace Oakland
- Rentals with lake access Oakland
- Rentals with a patio Oakland
- Rentals with a fire pit Oakland
- Rentals with outdoor seating Kennebec County
- Rentals with outdoor seating Maine
- Rentals with outdoor seating United States
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Saddleback Ski Mountain Maine
- The Camden Snow Bowl
- Maine Maritime Museum
- Rockland Breakwater Light
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Belgrade Lakes Golf Club
- Black Mountain of Maine
- Lost Valley Ski Area
- Sugarloaf Golf Club
- Range Ponds State Park





