
Holiday rentals with outdoor seating in Oakland
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Oakland
Guests agree: these rentals 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 A-Frame - Peaceful w/ Wood Fired Hot Tub
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)

Farmington! Walk to town & trails! Family-Friendly
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.

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.

Little Apple Cabin on 5 acres, amazing stargazing!
Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

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 .

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 and Hot Tub
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.

Kate-Ah-Den Cabin, a soul soothing escape.
Secluded & artistically built - a cozy cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec 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.

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.

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!
Popular amenities for outdoor seating rentals in Oakland
House rentals with outdoor seating

Family Getaway in Oxford Hills!

1830s Cape hosted by George & Paul

LUX Designer Private Waterfront

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Riverside

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

The Barn

Brook Ridge Retreat
Apartment rentals with outdoor seating

The Retro 2 bedroom

Comfy, Convenient Studio Apartment Near Downtown

Coastal, relaxing, light-filled + walkable

Sunny In-Town Camden Studio, 10% weekly discount

Midcoast In-Town Retreat

Village Top Floor With Riverview

A cute little gem in down east Maine

1820s Maine Cottage with Garden
Apartment rentals with outdoor seating

Battered Buoy - Newly renovated, two bedroom condo

Stylish 2BR | Balcony | River Views

Family Condo 5 min to Sugarloaf

Home away from home cozy new Apartment in Oakland

Waterviews + Sunsets + Boothbay/Gardens Aglow

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio

Harbor View Cottage Unit A 2 bedroom downtown

Ski In Ski Out, Pet Friendly, Pool & Hottub Access
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £119 | £134 | £154 | £134 | £192 | £211 | £228 | £223 | £192 | £148 | £142 | £134 |
| 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 £69 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Oakland holiday rentals include wifi 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!
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- Rentals with a washing machine and dryer Oakland
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- 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
- Dragonfly Farm & Winery
- Fox Ridge Golf Club
- Black Mountain of Maine
- Sandy Point Beach
- Bear Island Beach
- Maine Maritime Museum
- Sugarloaf Golf Club
- Eaton Mountain Ski Resort
- Brunswick Golf Club
- The Camden Snow Bowl
- Wadsworth Cove Beach
- Farnsworth Art Museum
- Narrow Place Beach
- Spragues Beach
- Three Island Beach
- Driftwood Beach
- Titcomb Mountain
- Lost Valley Ski Area
- Rockland Breakwater Light