Are there pet-friendly vacation rentals in Oakland?

Four-legged friends are welcome in Oakland. Choose from more than 20 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 20 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 house rentals in Oakland?

Experience the best of Oakland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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 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 a bbq area?

Absolutely! We offer over 10 cabin rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for Cabin Rentals in Oakland?

Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Oakland

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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, 145 reviews

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

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)

Top guest favorite

The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.

Home in Farmington

4.96 out of 5 average rating, 246 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

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

4.95 out of 5 average rating, 134 reviews

The Modern Maine Retreat

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.

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

4.97 out of 5 average rating, 87 reviews

Sister A-Frame in Woods (A)

Escape to one of our two sister A frames. This cozy cottages are nestled in the Oakland, Maine woods. Close proximity to major Route I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this A frame a perfect getaway for you and your family. Please note some amenities are seasonal. Feel free to check out our other listings!

Superhost

A sleeping area features a spacious bed with crisp white bedding and a decorative pillow. Natural light filters through two windows adorned with sheer curtains, enhancing the warm color of the purple walls. Two bedside lamps and a tufted bench are positioned nearby.

Apartment in Oakland

4.85 out of 5 average rating, 46 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, 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 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

5 out of 5 average rating, 120 reviews

The Rocky Road Camp on East Pond

Welcome to camp life on East Pond. A 1 bedroom home located in Oakland Maine. Your quiet weekend getaway awaits you. Located in central Maine. You will be about a 60 mile drive to the coast or about a 70 foot walk to the lake. Oakland is just a 20 minute drive to Waterville where both Colby and Thomas Colleges are located. East Pond is the host of several area summer camps. The camp will give you beautiful views of the lake. Sit on the deck and enjoy the loons and other lake activity.

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

4.95 out of 5 average rating, 65 reviews

Quaint Little Cottage

Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General and NorthernLight 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 10 minutes, or you can stay in and have delivery from one of our local eateries.

Guest favorite

A spacious living room features a large sectional sofa adorned with colorful cushions. A decorative area rug rests on hardwood flooring, complementing the light walls and artwork. A lamp emits soft light beside the sofa, while a potted plant adds a touch of greenery.

Home in Waterville

4.86 out of 5 average rating, 207 reviews

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 .

Superhost

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, 106 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.

Guest favorite

A serene lakeside view reveals calm waters reflecting the sky. Pine trees frame the scene, with a wooden railing suggesting a deck area. The landscape is peaceful, featuring a distant tree-lined shore under a clear blue sky.

Chalet in Belgrade

4.81 out of 5 average rating, 120 reviews

Visit Beautiful Home on Snow Pond

Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.

Top guest favorite

The cabin, with its artistic design, is nestled among trees and features a welcoming entrance path lined with stones. Surrounding foliage contributes to the serene environment, while a scenic view is visible in the distance.

Cabin in New Sharon

4.99 out of 5 average rating, 334 reviews

Kate-Ah-Den Cabin, a soul soothing escape.

Secluded & artistically built - a cozy cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

Top guest favorite

A modern kitchen space features metal shelving with glassware and utensils. A stainless steel table holds bowls and a vase of hydrangeas. A door leads to a closet, and a silver trash can is positioned nearby. Artwork is displayed on the wall, adding a touch of character.

Apartment in Waterville

4.99 out of 5 average rating, 178 reviews

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.

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Popular amenities for Oakland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Oakland

Top guest favorite

The entrance to the guest house is framed by a light grey door with an arched window. Potted plants and flowers are placed along the deck area, adding a touch of greenery. A few chairs are positioned nearby, inviting relaxation.

Farm stay in Oakland

5 out of 5 average rating, 11 reviews

Tranquil Farmhouse escape for Leaf-Peeping Season

Top guest favorite

A modern tiny cabin is surrounded by a dense forest, showcasing large windows and a spacious deck. Bright red chairs are positioned on the deck, inviting relaxation. The structure is elevated on a rock foundation, providing a serene view of the greenery.

Cabin in Rome

5 out of 5 average rating, 6 reviews

Modern Tiny Cabin Near Belgrade Lakes

Top guest favorite

A cozy sitting area is presented with a warm orange sofa and a comfortable gray armchair. A patterned area rug adds texture underfoot, while a small bookshelf displays various items. A wall-mounted TV is visible, and large windows provide natural light.

Guesthouse in Manchester

4.97 out of 5 average rating, 66 reviews

Private Studio in Manchester, ME

Top guest favorite

A serene view is captured from the cabin, showcasing a sloped roof in the foreground. Vast landscapes extend into the distance, featuring rolling hills and a blue sky adorned with clouds, highlighting the natural beauty of the Upper Kennebec Valley.

Cabin in Bingham

4.97 out of 5 average rating, 78 reviews

EcoCabin, for 2-4, 90 mi view

A welcoming entrance area features wooden walls and a light-colored floor. A small table is positioned beside the door, complemented by a wall-mounted painting. Two doors provide access to additional rooms, and natural light enters through the window on the right.

Guesthouse in Oakland

4.59 out of 5 average rating, 17 reviews

Sunny Studio in Belgrade Lakes Region

Top guest favorite

The rustic cabin is set among trees, featuring a spacious deck that offers panoramic views of the surroundings. Large windows allow natural light to illuminate the interior. The structure is elevated, with stairs leading down to the grassy yard, providing a seamless connection to nature.

Home in Belgrade

5 out of 5 average rating, 8 reviews

Salmon Lake Retreat

Guest favorite

A serene lake scene captures a fishing boat with two individuals navigating the water. Colorful foliage surrounds Snow Pond, providing a picturesque backdrop of autumnal hues on the trees and the shoreline. Nearby homes are visible, framed by lush greenery.

Guest suite in Oakland

4.97 out of 5 average rating, 30 reviews

Welcome to Squirrel Pocket!

Guest favorite

The cabin's exterior is bathed in warm light, highlighting the wooden structure and large windows. Lush greenery surrounds the building, creating a serene atmosphere. The porch area, bordered by a lattice design, adds to the inviting appearance. Trees frame the view, contributing to the secluded feel.

Cabin in Oakland

4.92 out of 5 average rating, 12 reviews

Your Path to Tranquility

Show all

Quick stats about vacation rentals in Oakland

Total rentals
70 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly vacation rentals in Oakland?
Four-legged friends are welcome in Oakland. Choose from more than 20 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 20 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 house rentals in Oakland?
Experience the best of Oakland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 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 a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cabin Rentals in Oakland?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Oakland

Top-rated vacation rentals in Oakland

Vacation rentals for every style

Popular amenities for Oakland vacation rentals

Other great vacation rentals in Oakland

Quick stats about vacation rentals in Oakland

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore