House holiday rentals in Oakland

Find and book unique houses on Airbnb

Top-rated house rentals in Oakland

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

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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 favourite

Home in Windham

4.94 out of 5 average rating, 125 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 favourite

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

Home in West Bath

4.85 out of 5 average rating, 101 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 favourite

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 favourite

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 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 Belgrade

5 out of 5 average rating, 119 reviews

SkyView Treehouse | Lakefront • Private Hot Tub

A peaceful retreat nestled in the trees along Belgrade Stream, just minutes from Belgrade Lakes Village and Messalonskee Lake. Built by three generations of our family, SkyView Treehouse is more than a stay — it’s a reflection of everything we value: peace, nature, comfort, and meaningful connection. Whether you’re planning a honeymoon, celebrating an anniversary, or surprising your partner with a birthday getaway, we’ve poured our hearts into making this a place where memories are made.

Guest favourite

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 favourite

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! ✨

Guest favourite

Home in Cushing

4.95 out of 5 average rating, 131 reviews

Dockside Retreat - 2025 booking quickly

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!

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What guests are saying

Postcard views, ocean front and idyllic cove

4.98 out of 5 average rating, 50 reviews1 month ago

Sitting looking out over the bay on a cold early March morning with the fire going was just the type of relaxation we were looking for. The photos don't do it justice. Had fun using the hot tub but just a little too chilly to use the outside fireplace, but Mihai had stocked the wood pile should we have been brave enough. Mihai lives right next door but you'd never know unless you needed him. We didn't. Everything worked. Clean, comfortable and tastefully furnished. A lot of thought has gone into renovating this house and it shows in the amenities. The only advice we'd give fellow travelers is the spiral stairwell leading upstairs to 2 of the 3 bedrooms is the smallest I've ever seen. Thought should be given to bringing small children. The master bedroom is on ground level. Otherwise enjoy. It's a magical place and we thank Mihai for being such a gracious host.

Home in Boothbay

What guests are saying

Log Cabin 15 acreshunting* snowmobile*skiing

4.75 out of 5 average rating, 20 reviews2 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, 12 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, 85 reviews5 days ago

Darryl's place was beautiful and just as described. my husband and I enjoyed the beautiful view from the hot tub and the movie room. Everything was easy to find and the welcome book had a lot of great information in it. My husband and I have already talked about going back.

Home in Woodstock

What guests are saying

Cliff House - Ocean Views! Architectural designed.

4.98 out of 5 average rating, 42 reviews3 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

Sebago Lake Beach Paradise

4.93 out of 5 average rating, 14 reviews4 months ago

Mike & Jess’s home is beautiful! We were celebrating our family Christmas, and this was the perfect location! The kitchen was well stocked and easy to prepare Christmas dinner. The living room was cozy and inviting. The primary bedroom is spacious and mattress was very comfortable. The kids loved the bunk room, and had so much fun hanging out there. It was so cold outside, but we never felt the chill indoors.

Home in Windham

What guests are saying

Mid-Century Modern walk to ocean

5 out of 5 average rating, 10 reviews3 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

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