Vacation rentals in Oakland

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Quick stats about vacation rentals in Oakland

  • Total vacation rentals

    Explore 80 vacation rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Oakland vacation 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 vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Chesterville
5 out of 5 average rating, 204 reviews

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)

Guest favorite
Apartment in Oakland
4.86 out of 5 average rating, 64 reviews

The heart of the Belgrade lakes

Located in a quiet country setting just minutes from the Oakland boat launch and McGrath pond, this place is stocked for your convenience with a coffee/tea/cocoa bar, air fryer, and full kitchen. Washer and dryer in unit. Swing set, pool, sand box, and trampoline out back. A short drive to downtown Waterville for shopping and entertainment. A 15 minute drive will take you to Maine General, Colby college, or Belgrade lakes. 20 minutes to Augusta. Owners on property to accommodate your needs.

Top guest favorite
A charming A-frame cabin is set amidst the lush greenery of the woods. The natural wooden exterior complements the surroundings, while two teal chairs invite guests to relax. A gravel pathway leads to the entrance, framed by large stones and trees casting gentle shadows.
Cabin in Oakland
4.98 out of 5 average rating, 143 reviews

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!

Top guest favorite
Condo in Oakland
5 out of 5 average rating, 107 reviews

Home away from home cozy new Apartment in Oakland

Escape to this newly built apartment in Oakland for a relaxing and peaceful getaway. Unwind on the porch while enjoying Maine’s beautiful wildlife, breathtaking sunsets, and star-filled skies. Conveniently located just minutes from Colby College, Thomas College, Snow Pond public beach/boat landing, Bowl in the Pines, and many local restaurants, shops, and outdoor attractions. Perfect for a vacation exploring beautiful Central Maine, visiting family, college visits, or business travel.

Top guest favorite
The guest cottage features a warm yellow exterior complemented by green trim. A small porch with a green chair invites relaxation amidst the surrounding trees and fallen leaves. The structure showcases a single door with a window, offering a glimpse of the peaceful wooded environment.
Tiny home in Belgrade
4.99 out of 5 average rating, 85 reviews

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.

Guest favorite
An outdoor deck is showcased, featuring a dining table surrounded by several chairs with colorful cushions. Potted flowers add vibrant touches, and a lounge chair is positioned nearby. Lush trees and a glimpse of the lake view are visible in the background, creating a serene atmosphere.
Home in Oakland
4.87 out of 5 average rating, 23 reviews

The Lake House on McGrath Pond | 4BR | Waterfront

Unwind year-round at this stunning lakeside home on McGrath Pond with 100+ ft of private water frontage. Sleeps 10 with 4 spacious bedrooms. Enjoy an open floor plan, fully equipped kitchen, large deck with lake views, WiFi & cable TV. Near Colby College and a short drive to Sugarloaf, Acadia, Bar Harbor & Freeport (LL Bean and outlets). Whether you're kayaking in summer, leaf-peeping in fall, or skiing in winter, this home has everything you need for a memorable Maine escape.

Guest favorite
A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.
Home in Sidney
4.87 out of 5 average rating, 112 reviews

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.

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 452 reviews

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.

Top guest favorite
A scenic lakeside view captures the sunset reflecting on the water, outlining the dock and several boats nearby. The grassy area leads to the water's edge, with trees providing natural framing to the picturesque setting of the Lake House.
Home in Oakland
4.91 out of 5 average rating, 108 reviews

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.

Top guest favorite
An open living area features a cozy seating arrangement next to an elegant stone fireplace. A circular coffee table sits on a textured area rug, and large windows provide ample natural light. A kitchen island with bar stools is visible, allowing for casual dining.
Home in Oakland
4.98 out of 5 average rating, 42 reviews

Ultra Spacious and Hosts are Gracious

Enjoy easy access to everything from this centrally located 3 bedroom/2.5 bath home. Newly renovated, very spacious sunlit home only 2 miles from I-95, public beach 1 mile, Colby College 6 miles, Thomas College 3 miles, Waterville 3 miles, Augusta 15 miles, and in the heart of the Belgrade Lakes chain. Many food options in all directions. Clean, comfortable, open, bright, and includes a private yard. This home sleeps up to 6 guests with its 3 queen beds.

Top guest favorite
The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.
Cabin in Augusta
5 out of 5 average rating, 123 reviews

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.

Guest favorite
Home in Oakland
4.95 out of 5 average rating, 84 reviews

Classy AF Home, walk across the street to Colby!

THE BOOKING CALENDAR OPENS ONE YEAR IN ADVANCE, INCLUDING GRAD WEEKEND. Lovingly renovated three bedroom home across the street from Colby College’s Senior Drive. My grandfather built our house in the 40’s, we have done all of the renovations ourselves to create open, inviting spaces with unique touches while maintaining the original footprint. Our home is a labor of love that we hope YOU love. *Pets ok w/ notice and 50$ fee*

Popular amenities for Oakland vacation rentals

When is the best time to visit Oakland?

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Avg. priceﺩ.ﺇ 694ﺩ.ﺇ 694ﺩ.ﺇ 896ﺩ.ﺇ 562ﺩ.ﺇ 841ﺩ.ﺇ 918ﺩ.ﺇ 918ﺩ.ﺇ 951ﺩ.ﺇ 790ﺩ.ﺇ 643ﺩ.ﺇ 635ﺩ.ﺇ 643
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Frequently Asked Questions

  • What are the best places to stay in Oakland?

    Stay near the waterfront or in Oakland’s residential neighborhoods to enjoy easy access to parks, local shops, and the lakefront. Areas near central Oakland are often chosen for their convenience and small-town atmosphere.

  • What are the best things to do in Oakland with kids?

    Families explore playgrounds at local parks, enjoy lakeside activities around Messalonskee Lake, and visit community events throughout the year. Public spaces often have open fields, walking paths, and places for picnics.

  • What are some of the best things to do in Oakland?

    Enjoy kayaking or fishing on Messalonskee Lake, walking tree-lined trails, and visiting the Oakland Area Historical Society for local stories. Community events and farmer’s markets add to the experience in warmer months.

  • How is the weather in Oakland?

    Oakland has cold winters around 12–37°F (-11–3°C), often with snow, and warmer summers near 59–79°F (15–26°C), with periodic rain. Spring and fall are transitional, bringing mild temperatures and lush or colorful scenery.

  • When is the best time to visit Oakland?

    Late spring through early fall is often recommended for enjoying lakeside activities, mild temperatures, and green landscapes. Autumn brings colorful foliage, while winter appeals to visitors interested in snow sports.

  • What are the best places to visit in Oakland?

    Explore the scenic Messalonskee Lake, the Oakland Waterfront Park, and the Oakland Area Historical Society for local heritage. Trails, parks, and family-owned shops give visitors a glimpse of the town’s character.

  • What are some hiking trails in Oakland?

    Local parks and conservation areas around Oakland have trails that wind through forests, along the lake, and across open meadows. These trails are frequently suggested for nature walks, birdwatching, and seasonal wildflower spotting.

  • What are some family activities we can do in Oakland?

    Gather for picnics in waterfront parks, paddle or fish on Messalonskee Lake, and explore walking trails suitable for all ages. Seasonal community events, like fairs or outdoor movie nights, are also family-friendly.

  • What are some of the best day trip ideas from Oakland?

    Explore nearby historic towns with main streets, visit other central Maine lakes, or discover local farms and markets that reflect the region’s rural traditions. Pine forests and nature preserves around Oakland encourage outdoor exploration.

  • Are there any pet friendly accommodations available in Oakland?

    Many accommodations around Oakland welcome pets, especially stays near the lake or wooded areas. Park access and local trails make it easy to explore the outdoors with your dog.

  • What are some local tips for visiting Oakland?

    Locals recommend bringing layers due to changing weather, supporting family-owned shops, and exploring less-trafficked lake coves for quiet moments. Early mornings on the water can provide a peaceful start to your day.

  • What is Oakland known for?

    Oakland is often known for its lakeside setting on Messalonskee Lake, community festivals, and recreational opportunities connected to Maine’s outdoors. Its local businesses and welcoming neighborhoods reflect the town’s New England heritage.

  • What are the best hidden gems to explore in Oakland?

    Explore community trails winding through wooded areas, lesser-known access spots along Messalonskee Lake, and locally run farm stands. Quiet art galleries or seasonal events sometimes pop up around central Oakland.

  • What are the best foods to try in Oakland?

    Sample locally caught fish, traditional New England chowder, wild blueberry desserts, and baked goods from local markets. Farm stands around Oakland sometimes feature seasonal produce and maple syrup.

  • What should I bring for a trip to Oakland?

    Bring clothing for variable weather, sturdy shoes for trails, and swimwear or gear for lake activities in summer. A reusable water bottle and a camera are practical for outdoor adventures year-round.

  • What is the nightlife in Oakland like?

    Oakland has a relaxed, small-town vibe in the evenings, with local pubs and gathering spots that highlight community connections. Live music or casual dining options can be found around central areas, and nearby towns may have additional nightlife offerings.

  • What are the most popular events or festivals in Oakland?

    Oakland has community traditions such as summer waterfront festivals, seasonal farmers markets, and parades around major holidays. Outdoor concerts and local craft fairs are also frequently suggested by residents.

  • Are there family friendly vacation rentals in Oakland?

    Oakland has a variety of family-friendly vacation rentals, including lakefront cottages and homes with open layouts. Many have spacious yards and easy access to parks and playgrounds.