
Holiday houses in Oakland
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Top-rated holiday rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness and more.

Off-Grid Escape. 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- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Lakefront 3 bedroom pet friendly on Messalonski
Make memories of a lifetime at this unique and cozy family-pet-friendly private lakefront on Messalonskee. Beautifully manicured lawn/gardens with a fire pit surrounded by the peaceful sounds of nature. A large dock to take in the spectacular views of bald eagles, loons, and blue herons. Owners boat is attached for occasional boat rides. This guesthouse is newly built with a covered porch overlooking the serene lake. Comes w/3 kayaks, 2 paddle boards, a paddle boat, life jackets, and a canoe

Updated 4br Family Home Near Belgrade Lakes
Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

Sister a-frame in Woods (A)
Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!

Lakefront home w/Dock & Fire Pit + Pet Friendly
Nestled right on the picturesque McGrath Pond, this cozy retreat is perfect for you and your loved ones. The back deck is perfect for BBQs or end your day around the fire pit! Enjoy 100' of your own private lakefront where you can paddle board, kayak or keep your own smaller boat at your own dock in this protected shallow cove. Explore the 7 miles of shoreline or check out Ellis aka Salmon Lake, by boating through the well marked ''Narrows'' thoroughfare where the public boat ramp access.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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.

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.

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.
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

Privacy with spectacular waterfront, Lilla Stuga.

Mountain Escape | Views • Firepit • Near Sugarloaf

Lakefront cottage in Belgrade Lakes

The Round House in Bryant Pond

Cabin In The Birches #2

The Rocky Road Camp on East Pond

Le cabrera apartments rental in Madison

Downtown Augusta - 1 Bedroom Loft
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $324 NZD | $324 NZD | $418 NZD | $262 NZD | $392 NZD | $428 NZD | $428 NZD | $443 NZD | $368 NZD | $300 NZD | $296 NZD | $300 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Oakland?
Four-legged friends are welcome in Oakland. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oakland?
Yes! Work meets play with ease at over 30 vacation rentals in Oakland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Oakland?
Oakland has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Oakland?
Experience the best of Oakland with our cabin rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oakland have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Oakland. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Oakland have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Oakland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oakland have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oakland?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Oakland

Total holiday rentals
Explore 80 holiday rentals in Oakland

Nightly prices starting at
Oakland holiday rentals start at $86 NZD per night before taxes and fees

Verified guest reviews
Over 2,630 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Oakland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace 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
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- Pemaquid Beach
- Saddleback Ski Mountain Maine
- Coastal Maine Botanical Gardens
- The Camden Snow Bowl
- Rockland Breakwater Light
- Maine Maritime Museum
- Farnsworth Art Museum
- Camden Hills State Park
- Black Mountain of Maine
- Cellardoor Winery
- Moose Point State Park
- Samoset Resort
- Maine Lighthouse Museum
- Hollywood Slots Hotel & Raceway
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- Sugarloaf Golf Club
- Range Ponds State Park





