
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.

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)

Room B with private entrance, bathroom & hot tub
Room B is a small (10’ x 10’) but cozy room with full size bed with luxury mattress and private bathroom (5’ x8’) with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

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.

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!

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.

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.

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

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.

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.

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

Sunny 2-BR 5 min to Bates & River Trails

1830s Cape hosted by George & Paul

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Peaceful Getaway at The Ledges

Riverside

The Riverfront Retreat - 27 minutes to Sugarloaf!

Lakefront: Private Hot Tub, Sauna & Free Massages!

Sheepscot Harbour Cottage/waterview
Apartment rentals with outdoor seating

Fernald's Backside

The Retro 2 bedroom

Coastal, relaxing, light-filled + walkable

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
Apartment rentals with outdoor seating

1BR water-view condo with deck & WiFi

Stylish 2BR | Balcony | River Views

1BR | Water Views | Deck | Full Kitchen

1BR Waterview | Deck | Partial AC

Home away from home cozy new Apartment in Oakland

Little Eddy with Big Sunsets!
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $199 SGD | $225 SGD | $257 SGD | $225 SGD | $321 SGD | $353 SGD | $381 SGD | $372 SGD | $321 SGD | $248 SGD | $237 SGD | $225 SGD |
| 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 $115 SGD 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 firepit Oakland
- Rentals with a kayak Oakland
- Waterfront rentals Oakland
- Rentals with a washing machine and dryer Oakland
- Rentals with a patio Oakland
- House rentals Oakland
- Rentals with a fireplace Oakland
- Pet-friendly rentals Oakland
- Family-friendly rentals Oakland
- Rentals with lake access 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
- Spragues Beach
- Sugarloaf Golf Club
- Titcomb Mountain
- Wadsworth Cove Beach
- Islesboro Town Beach
- Rockland Breakwater Light
- Farnsworth Art Museum
- Narrow Place Beach
- Lost Valley Ski Area
- North Point Beach




