House vacation rentals in Oakland

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Top-rated house rentals in Oakland

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

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Guest favorite

A serene outdoor space is bordered by trees and features a gravel area with seating around a fire pit. A wooden deck extends from the cabin, providing views of the nearby river, enhancing the natural landscape.

Home in Naples

4.99 out of 5 average rating, 116 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Top guest favorite

Home in Stratton

4.97 out of 5 average rating, 112 reviews

Sugarloaf and Flagstaff Lake Area Vacation Rental

Nestled in a quiet private neighborhood, yet close to area restaurants & amenities, this is the perfect house for the outdoor enthusiast. The open floor plan, comfortable & clean space, & entertainment system are ideal for relaxing after a full day. Kayaks are available for use on Flagstaff lake. Close to hiking & biking trails, 7 mi to Sugarloaf Mountain , 1.5 mi to public boat launch. You will have a fire-pit, outdoor dining area, deck, propane Weber grill, & covered porch. Stratton/Eustis, ME

Superhost

The living room features a light-colored sofa paired with two patterned armchairs, complemented by natural light from large windows. A plant sits in the corner, and a textured area rug covers the hardwood floor, creating a welcoming space. Ceiling fans enhance airflow.

Home in Owls Head

4.79 out of 5 average rating, 124 reviews

Bayview- Lobster Dinner included!

Come enjoy this newly updated house! This rental includes a lobster dinner for all guests, caught by a local fisherman and delivered to your door in the same day! Seasonal water views of Rockland Lighthouse. With expansive backyard and deck, great for grilling, lounging and visiting. Local artwork decorate the walls and wood floors run throughout. The kitchen is well stocked for your needs. The rooms are equipped with flatscreen smart TVs with Roku and Amazon Prime. Come experience real Maine!

Top guest favorite

A light-filled entryway features a staircase leading down to an open space. A wooden dining table is set beside large windows offering views of the exterior greenery. A wall clock hangs near the doorway, adding a touch of practicality to the modern design.

Home in Windham

4.94 out of 5 average rating, 127 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Guest favorite

The exterior of a multi-level home is showcased against a backdrop of vibrant autumn foliage. The structure features a combination of wood and metal siding, with large windows reflecting natural light. A gravel driveway leads to the entrance, surrounded by trees displaying fall colors.

Home in Carrabassett Valley

4.92 out of 5 average rating, 37 reviews

A Perfect Home For Family Summer Vacations!

This expansive and family-oriented home is situated on Sugarloaf, offering 5 bedrooms, 4.5 bathrooms, two spacious living areas, and a generously sized kitchen and dining space. Located on the Winter shuttle route and within close proximity to hiking/biking trails, the Carrabassett River and golf course! Enjoy the gas fireplace after a day on the slopes or a game of ping pong with the family! Nestled in the mountains, this exquisite home presents an ideal setting for your upcoming vacation.

Superhost

A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.

Home in West Bath

4.85 out of 5 average rating, 103 reviews

Oak Leaf

Take it easy at this unique and tranquil getaway. This sweet cottage offers scenic water views and much more. Overlooking the New Meadows river, it is nestled in a quiet area and surrounded by 100 yr old oak trees. It is loaded with charm yet offers modern amenities. You feel tucked away, yet the place is only 10 to 20 minutes from beautiful beaches, hiking, fine dining, and shopping opportunities. Enjoy beautiful sunsets from the back porch and cozy up to fire pit while you make memories.

Guest favorite

A screened-in porch features comfortable seating, including rocking chairs, and a coffee table. Views of the peaceful lake and lush greenery are visible through large windows. Natural light enhances the relaxing atmosphere, inviting moments of leisure while enjoying the scenic surroundings.

Home in Litchfield

4.92 out of 5 average rating, 135 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Guest favorite

A renovated house is visible along the water, surrounded by lush greenery. Two docks extend into the lake, with one seating area under a sunshade. The yard features a well-maintained lawn and cut wood nearby, creating a peaceful lakefront setting.

Home in Hartford

4.9 out of 5 average rating, 20 reviews

Maine Lake Escape* Hot Tub*

45 minute drive from Sunday River. New 7-Person Hot Tub. Newly renovated house on the water. A few steps from the backyard puts you right in the water. Each room has a mini split heat\AC unit. Fire rock with cut wood and propane fire pit allows you to choose which type of camp fire you would rather enjoy. Perfect Maine Lake getaway equipped with 5 kayaks, 1 paddle board, and 1 canoe. Two docks, one with a sitting area and sun shade. Bedrooms come fully furnished with bed linens.

Guest favorite

Home in Boothbay

4.83 out of 5 average rating, 6 reviews

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Guest favorite

A serene river scene is captured, reflecting lush green trees along the banks and a clear blue sky above. The calm water displays soft ripples, while the surrounding foliage offers a tranquil, nature-filled environment ideal for relaxation and wildlife observation.

Home in Belfast

4.91 out of 5 average rating, 23 reviews

Between the Dams

Enjoy Maines Best. Coffee mornings on the dock on the river right outside your back door. Working waterfront town located 4 minutes away. This location is true Maine in an old & well loved cottage that has nature & todays tech with high speed internet, smart TVs and office workstation. Two outside sitting areas. Picnic table & BBQ grill. Fire pit on the waters edge. Spy birds, river otters, beavers, Bald Eagles and more. The house can sleep 8-10 comfortably. Art retreat vibes throughout

Guest favorite

A modern, two-story home is set against a backdrop of trees, featuring large windows that invite natural light. A spacious deck extends out, with multiple wooden chairs arranged in the foreground to create a welcoming outdoor seating area.

Home in Oakland

5 out of 5 average rating, 24 reviews

Peaceful 5 bedroom 4.5 bath waterfront house

This newly built (2021) Colonial has over 75 ft of shore frontage adjacent to the hosts 6 bedroom Cape Cod style house. Centrally located minutes from Intersate 95 and Colby College , Thomas college, and other Belgrade lakes destinations. Bar Harbor and Acadia National Park are only a couple hour drive through scenic countryside. In the winter you can ice fish, cross country ski, snowmobile, or enjoy the quite of the lake. Sugarloaf and Sunday River ski resorts are a 60 minute drive.

Top guest favorite

A wooden deck leads down to a sandy beach, surrounded by lush greenery. Several blue Adirondack chairs are positioned for relaxation, with steps providing access to the beach area. The lake house is visible in the background, framed by tall trees and a clear sky.

Home in Harrison

5 out of 5 average rating, 6 reviews

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

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What guests are saying

Log Cabin 15 acreshunting* snowmobile*skiing

4.75 out of 5 average rating, 20 reviews3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

Home in Otisfield

What guests are saying

Charming 3 BR + Loft & Workspace - Close to Sebago

5 out of 5 average rating, 56 reviews6 months ago

Jared was a responsive and welcoming host. From the beginning, he was curious about our check in and our overall stay; he always wanted to be available if needed and gave multiple recommendations for our weekend. His house was welcoming and warm, and had everything my family needed. The area was beautiful and my family is already discussing coming back next year. If you’re thinking about a trip to Maine, this home should definitely be a consideration!

Home in Naples

What guests are saying

NEW! Serenity Escape: Countryside Retreat/HOT TUB

5 out of 5 average rating, 13 reviews1 month ago

This place for was perfect for our ski trip. The home had plenty of beds for all of us and enough room for us to all hang out. The hot tub was an excellent addition to relax after a long day of skiing. The house is very private and gives that secluded feeling. Overall, we loved the house and would totally stay again.

Home in Harrison

What guests are saying

Modern Lake Front Home with Hot Tub

4.9 out of 5 average rating, 70 reviews1 month ago

Spenser's place was pretty perfect for our needs. Loved the hot tub, lots of towels, lots of kitchen supplies and room for the 7 of us. Would suggest have a few more chairs for the dining room since the home can fit 8 people. We just took a chair from the deck, which was fine. There were a lot of flies just hanging out with us, a few lady bugs too. The many flies were slow, so easy to catch. But still 5 stars! Thanks so much!

Home in Liberty

What guests are saying

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake

5 out of 5 average rating, 87 reviews1 week ago

A true gem! Its impossible not to be impressed by the mountain views that this place offers, for me it's one of a kind! You can see they care a lot about the house, the movie theater is a lot of fun and adds a lot to the house, the rooms are spacious and comfortable, the arcade and the hot tub are the cherry on top. The host was nice and responsive the whole trip! I would love to come back and spend more time in this amazing home! Don't think twice, just book it

Home in Woodstock

What guests are saying

Cliff House - Ocean Views! Architectural designed.

4.98 out of 5 average rating, 42 reviews4 months ago

By far the best home away from home that any of us have ever stayed at. Better than the photos. Cleanest Airbnb I’ve ever stayed at. Can’t say enough. I am so glad we booked Mark’s place for our Christmas vacation, it was definitely one to be remembered.

Home in Northport

What guests are saying

Mid-Century Modern walk to ocean

5 out of 5 average rating, 10 reviews4 months ago

The house and space are welcoming and comfortable. The multiple levels of the living/dining/kitchen space are challenging for a person with mobility issues, but we managed, and it was worth the effort. The openness of that area and the light filled space on a sunny day are lovely. The artwork is stunning and plentiful! The kitchen is modern and well supplied. We were there Christmas week, cold and snowy, so we weren’t out much, but the area has excellent restaurants, and a really good cafe just across the street. It was a perfect place for us to stay and welcome other family members for time together during the holidays.

Home in Rockport

What guests are saying

5 Bedroom Lake House + HGuest House with Hot Tub!

4.91 out of 5 average rating, 82 reviews3 months ago

We had a great time on the pond. The location was great. It was fairly quiet but not too far of a drive from whatever you could possibly need. The downstairs was perfect for our teens to hang out. They even made forts with the magnetic tiles, they were a huge hit…almost as much as the espresso machine was for the adults. Our families did some ice fishing and had great luck. Would definitely stay here again.

Home in Casco

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