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

Home in Belgrade

5 out of 5 average rating, 119 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!

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

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

Home in Windham

4.94 out of 5 average rating, 124 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

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

Home in West Bath

4.85 out of 5 average rating, 100 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.

Superhost

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

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

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

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

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! ✨