
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.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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)

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.

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.

[Trending Now]Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

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 .

Modern Tree Dwelling w/Water Views+Cedar Hot Tub
Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our 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!

Hallowell Hilltop Home with Hot Tub & Sauna
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

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.

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!

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
Holiday House Rentals with Outdoor Seating

Farmington and UMF! Walk to town! Skiers welcomed!

Cute Midcoast Cottage w Hot Tub

Peaceful Getaway at The Ledges

Entire House/Mill/modern vintage on 35 Acre Pond

Lakefront: Private Hot Tub, Sauna & Free Massages!

Sheepscot Harbour Cottage/waterview

Rustic Farmhouse at Oxbow Brewery

Quiet 2 bedroom home, snowmobile from property.
Apartment rentals with outdoor seating

The Retro 2 bedroom

Comfy, Convenient Studio Apartment Near Downtown

The perfect getaway - Camden/Rockport/Rockland

Coastal Vintage Living

Sunny In-Town Camden Studio, 10% weekly discount

Midcoast In-Town Retreat

A cute little gem in down east Maine

1820s Maine Cottage with Garden
Condo rentals with outdoor seating

1BR water-view condo with deck & WiFi

Battered Buoy - Newly renovated, two bedroom condo

Great Location For All Your Outdoor Adventures!

Stylish 2BR | Balcony | River Views

Family Condo 5 min to Sugarloaf

Home away from home cozy new Apartment in Oakland

Cozy Waterview & Golden Sunsets

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $269 NZD | $303 NZD | $347 NZD | $303 NZD | $433 NZD | $477 NZD | $515 NZD | $503 NZD | $433 NZD | $335 NZD | $321 NZD | $303 NZD |
| 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 |
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 $156 NZD per night before taxes and fees

Verified guest reviews
Over 1,330 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, Wi-Fi and Pool across Oakland rentals

4.9 Average rating
Oakland stays are highly rated by guests—averaging 4.9 out of 5!
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- 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
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Black Mountain of Maine
- Fox Ridge Golf Club
- Sandy Point Beach
- Dragonfly Farm & Winery
- The Camden Snow Bowl
- Maine Maritime Museum
- Bear Island Beach
- Brunswick Golf Club
- Eaton Mountain Ski Resort
- Sugarloaf Golf Club
- Spragues Beach
- Titcomb Mountain
- Wadsworth Cove Beach
- Islesboro Town Beach
- Lost Valley Ski Area
- Farnsworth Art Museum
- Rockland Breakwater Light
- Narrow Place Beach
- North Point Beach




