House holiday rentals in Oakland

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Top-rated house rentals in Oakland

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Guest favourite

Home in Belgrade

4.99 out of 5 average rating, 116 reviews

SkyView Treehouse- Luxury Waterfront Retreat

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

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 favourite

Home in Windham

4.93 out of 5 average rating, 117 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.

Superhost

Home in Carrabassett Valley

4.91 out of 5 average rating, 34 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.

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Home in Litchfield

4.92 out of 5 average rating, 133 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 favourite

Home in Hartford

4.88 out of 5 average rating, 16 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 favourite

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 favourite

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 favourite

Home in Freeport

4.99 out of 5 average rating, 69 reviews

Freeport Escape -Downtown, Fire-pit, 3 Kings w/ AC

The Freeport Escape Built in the early 1900s, this home has the old charm yet all the modern amenities you could think of. Come stay directly in the heart of Freeport, walkable to all the shopping, restaurants, breweries, and Amtrak station located in town. This corner lot provides privacy and is the perfect place to enjoy warm summer nights by the fire-pit, grilling out on the porch. We got you covered to enjoy the beautiful Maine fall and winter by the fireplace inside. STRR-2022-82

Guest favourite

Home in Cushing

4.95 out of 5 average rating, 121 reviews

Dockside Retreat - Fall/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

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.

Guest favourite

Home in Carrabassett Valley

4.96 out of 5 average rating, 51 reviews

Ski House! Adorable 3BR/2BA home at Sugarloaf!

Adorable 3BR/2BA cape on a quiet road in a nice neighborhood. House sleeps 10. Main floor master bedroom queen with ensuite bathroom. Upstairs 2 bedrooms have a queen and 2 twins and share a full bath. Full finished basement bunk room/tv room sleeps 4. Main floor has open concept kitchen/dining/living area with TV.