
Holiday houses in Oakland
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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 $72 AUD 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!
Top-rated holiday rentals in Oakland
Guests agree: these stays 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)

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

Quaint Little Cottage
Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. We host short or long term. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General Hospital, centrally located between Waterville and Augusta, and 1 hour to the Maine coast as well as ski mountains. Enjoy hiking, fishing, exploring Maine, and more! For great dining options your commute is 5-10 minutes, or you can stay in and have delivery from one of our local eateries.

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.

epicurean feast with zen like surroundings
My sister and i will welcome you to our guest cottage on a quiet lake in Belgrade. We are including a dropped off gourmet breakfast-you pick the time, between 7:30 and 9:00. We include waterfront access as well as use of a kayak. We are located on a beautiful lake in the middle of the woods. Peaceful and absolulely quiet. We will practice extreme sanitation as well as social distancing. One well behaved dog is welcome as long as they are not left alone in the cottage- dog bed supplied.

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.

Halcyon Ridge
Halcyon Ridge is owned by Lynn & Chuck Hadyniak, who live nearby. Lynn & Chuck moved out of New Jersey years ago to get away from the hustle & bustle, & raise a family in peace. They love Freedom for its quiet & natural beauty, & would love to host people at Halcyon Ridge who also want to escape the noise. Stargazers will be delighted: low humidity, expansive view of the southeastern sky, & next to no light pollution, make for wonderful viewing. Rest. Relax. Recharge.

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.

Peaceful retreat in Oakland Maine minutes to lake
Offering 3 Bedrooms, 2+ bathrooms, fully stocked kitchen, pool and fire pit — your Belgrade Lakes farmhouse getaway just an easy 15 minutes to Waterville and Colby College. Enjoy sunny afternoons by the pool, boating or kayaking is just a short 5-minute drive to Messalonskee Lake. Relax in the evenings around the fire pit. Fully stocked kitchen, peaceful country setting, and the perfect mix of comfort and convenience. Summer dates fill quickly — book early!

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

Modern Tiny Cabin Near Belgrade Lakes

Studio Lakefront Dog Friendly | Patio | Firepit

Mountain Escape | Views • Firepit • Near Sugarloaf

Clean & Comfortable, 2nd Fl Apt

The Rocky Road Camp on East Pond

The MushRoom

Former Hydro Station

Cozy Lakeside Cottage in Oakland, ME
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $273 AUD | $273 AUD | $353 AUD | $221 AUD | $331 AUD | $362 AUD | $362 AUD | $375 AUD | $311 AUD | $253 AUD | $250 AUD | $253 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 |
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 vacation rentals in Oakland?
Oakland has more than 50 family-friendly stays. 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 house rentals in Oakland have wifi?
Absolutely! We offer over 20 house 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 air conditioning, over 20 homes with a bbq area, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Montreal Holiday rentals
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- 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
- Rentals with outdoor seating 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
- 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
- Maine Lighthouse Museum
- Cellardoor Winery
- Moose Point State Park
- Belgrade Lakes Golf Club
- Hollywood Slots Hotel & Raceway
- Black Mountain of Maine
- Lost Valley Ski Area
- Sugarloaf Golf Club
- Range Ponds State Park





