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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 G$10,466 GYD 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
A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.
Home in Starks

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

LocationFamilyHiking

4.94 out of 5 average rating, 173 reviews
Guest favorite
Cabin in Smithfield

Waterfront private beach. 4-seasons Maine escape.

Waterfront cabin on North Pond in Smithfield, Maine with a private sandy beach just steps from the door. This four-season retreat sleeps up to 10 guests with 3 bedrooms and 2.5 bathrooms. Swimming, kayaking and sunsets in summer, fall foliage views, and direct ITS 87 access in winter for snowmobiling! Easy access for ice fishing. Peaceful, private setting close to Waterville & Augusta. Sugarloaf nearby. Ideal for families, couples, and year-round Maine lake getaways. Book now and unwind! Relax!

FamilyLocationAccuracy

4.83 out of 5 average rating, 18 reviews
Top guest favorite
A well-organized kitchen features white cabinetry with glass shelving displaying decorative dishware. A small wooden dining table with chairs is positioned near a window, providing natural light. Stainless steel appliances are included, alongside a sink and counter space for meal preparation.
Home in Oakland

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.

ValueFamilyDecor

4.97 out of 5 average rating, 96 reviews
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

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!

FamilyLocationLong stay

4.98 out of 5 average rating, 148 reviews
Top guest favorite
Condo in Oakland

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.

LocationFamilyLaundry

5.0 out of 5 average rating, 112 reviews
Top guest favorite
The lakeside cottage features multiple decks, offering expansive outdoor space and views of the surrounding trees. A terraced lawn leads down to the water's edge, where a rocky shoreline can be seen. The building's warm color complements the natural setting.
Home in Belgrade

Enjoy a gorgeous sunset steps away from Great Pond

Relax, swim, boat, kayak and enjoy time with your family at beautiful Great Pond Lake. This home is located steps from Great Pond and has 3 lovely decks from which to enjoy the sunset. Great Pond is located only an hour North of Portland in Belgrade Maine. Belgrade Lakes Golf Club is one of the top rated courses in Maine and is a public course. There is easy access to multiple hiking trails. There are also many winter activities - snow shoeing, cross country skiing and ice skating!

FamilyValueHospitality

5.0 out of 5 average rating, 40 reviews
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

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.

FamilyLocationQuiet

4.88 out of 5 average rating, 25 reviews
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

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.

FamilyLocationQuiet

4.89 out of 5 average rating, 114 reviews
Top guest favorite
The farmhouse exterior is illuminated by soft outdoor lighting at dusk, casting a welcoming glow. A spacious deck with seating overlooks the adjacent pool, while the expansive lawn features a mixture of landscaped and natural elements. The peaceful surroundings invite a sense of tranquility.
Farm stay in Oakland

Fall Foliage Farmhouse Getaway in Oakland

**Available for short term rental from November 2026 thru May 2027.** Send inquiry for more information. 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. ATV & Snow mobile trails abut property. Relax in the evenings around the fire pit. Fully stocked kitchen, peaceful country setting, and the perfect mix of comfort and convenience.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 26 reviews
Top guest favorite
A corner of the enclosed front porch showcases a wicker chair adorned with a colorful throw blanket. A small, coral-colored table holds a coffee cup, while a potted plant adds a touch of greenery. Natural light streams through the large windows.
Home in Waterville

Sterling House

1960’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as MaineGeneral Thayer Hospital. We are a pet-free home with NO central A/C - fans only. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

FamilyValueKitchen

4.91 out of 5 average rating, 179 reviews
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

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.

FamilyLocationCheckout

5.0 out of 5 average rating, 130 reviews
Top guest favorite
Home in Oakland

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*

LocationFamilyHospitality

4.95 out of 5 average rating, 86 reviews

Popular amenities for Oakland vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Oakland

Superhost
Apartment in Oakland

The heart of the Belgrade lakes

LocationFamilyAccuracy

4.85 out of 5 average rating, 71 reviews
Guest favorite
A scenic lakeside area features four dark wooden chairs arranged around a stone fire pit. Smooth rocks and gentle waves are visible in the background, reflecting the sunlight, while trees and shrubs border the landscape, creating a serene outdoor space.
Cottage in Oakland

Pet-Friendly Lakefront Camp w/ Kayaks & Sunsets

LocationValueSleep quality

4.9 out of 5 average rating, 39 reviews
Top guest favorite
The exterior of the spacious lakeside home is shown at dusk, with soft lights adorning the entryway. Surrounding trees provide natural privacy, while the serene lake glimmers nearby. A welcoming entrance is visible, offering easy access to the charming surroundings.
Home in Sidney

"Sweet Sunsets"Spacious 4 b/r Lakefront Home

LocationFamilyNearby

4.9 out of 5 average rating, 39 reviews
Guest favorite
A two-story house showcases a charming design with a gray exterior and red front doors. Green trees frame the property, providing a natural backdrop. The inviting driveway leads to the entrance, with windows allowing for ample natural light.
Home in Oakland

Leaf peeper paradise 4br central Maine

ValueFamilyCleanliness

4.92 out of 5 average rating, 159 reviews
Top guest favorite
A deck area features two green Adirondack chairs positioned to face the tranquil waters of East Pond. Natural greenery from surrounding trees provides a sense of privacy, enhancing a peaceful atmosphere for relaxation by the lake.
Cottage in Oakland

The Rocky Road Camp on East Pond

FamilyLocationCheckout

5.0 out of 5 average rating, 125 reviews
Top guest favorite
Cabin in Oakland

Cozy Lakeside Cottage in Oakland, ME

FamilyLocationHospitality

5.0 out of 5 average rating, 12 reviews
Guest favorite
A serene lakeside area is presented, featuring a wooden deck with several Adirondack chairs facing the water. A small boat is docked nearby, and colorful canoes are stored on the grass. Lush green trees surround the tranquil blue lake.
Home in Oakland

Peaceful 5 bedroom 4.5 bath waterfront house

LocationFamilyAccuracy

5.0 out of 5 average rating, 40 reviews
Top guest favorite
A spacious deck overlooks the water, furnished with several lounge chairs arranged for relaxation. The green lawn extends towards the lake, providing a serene outdoor space surrounded by trees, enhancing the tranquil atmosphere.
Cottage in Oakland

Lakefront camp with kayaks, swimming and views!

LocationFamilyAmenities

4.95 out of 5 average rating, 38 reviews

When is the best time to visit Oakland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,560 GYDG$39,560 GYDG$51,072 GYDG$47,514 GYDG$51,909 GYDG$52,328 GYDG$52,328 GYDG$54,212 GYDG$45,002 GYDG$36,630 GYDG$36,211 GYDG$36,630 GYD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

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.

Destinations to explore