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, 108 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.

Guest favorite

A cozy stone fireplace is featured against a natural stone wall, providing warmth to the open living space. Sunlight filters through large windows, illuminating a corner nook with a blue cushion labeled 'LAKES'. Warm wooden accents complement the rustic aesthetics.

Home in Belgrade

5 out of 5 average rating, 118 reviews

SkyView Treehouse | Lakefront • Private Hot Tub

With direct access to Belgrade stream & Messalonskee lake, this treehouse is nestled within the pine trees on the waterfront of Belgrade Stream. Located 20 mins away from Colby College, we welcome families of students to come and stay with us during such a monumental transition. We are 10 mins from the Maine State Capitol, 10 mins from downtown Belgrade Lakes, an hour from Acadia National Park, and 45 mins from Sugarloaf. Our space is ideal for all vacationers looking for a getaway or adventure!

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!

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

4.93 out of 5 average rating, 118 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 spacious home is depicted, showcasing a two-story structure with a combination of brick and wood. Snow blankets the ground, and large windows invite ample natural light. Tall trees surround the property, contributing to a serene, mountainous atmosphere.

Home in Carrabassett Valley

4.92 out of 5 average rating, 37 reviews

High End Private Home on Sugarloaf Shuttle Route!

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 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, 134 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

4.89 out of 5 average rating, 18 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

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, 21 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.

Guest favorite

A dining area is illuminated by natural light, featuring a dark wooden table with a decorative centerpiece of fruit. Large windows offer a view of the water and nearby boats, while comfortable seating is arranged alongside the table.

Home in Cushing

4.95 out of 5 average rating, 126 reviews

Dockside Retreat - Winter discounted pricing

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Superhost

A winter landscape features a wide expanse of untouched snow leading to a serene bay. Snow-covered homes dot the shoreline, and trees line the background against a clear blue sky, providing a peaceful view of the water.

Home in Owls Head

4.9 out of 5 average rating, 206 reviews

Comfortable, Close to Town Home, with Oceanview.

This conveniently located home is 1.5 miles from downtown Rockland and all the local festivals. It is a short drive to Camden & Thomaston and only minutes to the Farnsworth Art Museum & Transportation Museum . Centrally located, about 1.5 hours from both Portland and Bangor and only 2 hours from Acadia National Park. Local amenities include, beaches, scenic hiking trails, light houses, lakes, golf, skiing, art galleries, and of course lobsters.