Title: Oakland Guest Houses from CA $372 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d140470.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d140470.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d140470.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.ca/Oakland.d140470.Destination-Travel-Guides) ![Overlooking Long Pond from Frenche's Mountain, Rome,Me. Very easy hike, less than a mile round trip, through the woods. ](https://images.trvl-media.com/place/183294/94640f69-e5f6-46b9-9d25-cbf58ad86730.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marc Maheu # Search Guest Houses in Oakland from CA $372 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakland guest houses ![Property grounds](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/20d8d18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/e9d8ab8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/5d995857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/d4256d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore [](https://www.expedia.ca/Oakland-Hotels-Lakefront-3-Bedroom-Pet-Friendly-On-Messalonski.h107340207.Hotel-Information) Oakland 10/10 Exceptional (15) "Diane was amazing and accommodating! Our stay was an amazing success!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Livia S. CA $194 CA $372 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Oakland-Hotels-Lakefront-3-Bedroom-Pet-Friendly-On-Messalonski.h107340207.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12®ionId=140470&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Guest-Houses.d140470-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Guest-Houses.d140470-aaGuestHouses.Travel-Guide-Accommodation) ## Top Oakland Hotel Reviews ![Hampton Inn Waterville](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/3c11b972_y.jpg) ### Hampton Inn Waterville 10/10 Excellent "Clean room, great staff, nice breakfast" [](https://expedia.ca/Augusta-Hotels-Hampton-Inn-Waterville.h721075.Hotel-Information) ![Hampton Inn Augusta](https://images.trvl-media.com/lodging/6000000/5190000/5185100/5185016/bf2caaca_y.jpg) ### Hampton Inn Augusta 10/10 Excellent "We were there for one night. Nice, clean, , quiet, basic hotel. Free hot breakfast was surprisingly delicious. Staff were friendly. It was a great place to stay. I would stay again. " [](https://expedia.ca/Augusta-Hotels-Hampton-Inn-Augusta.h5185016.Hotel-Information) ![Maine Evergreen Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/790000/787600/787572/42d3f26f_y.jpg) ### Maine Evergreen Hotel, an Ascend Collection Hotel 10/10 Excellent "Clean & nicely decorated room & hotel. " [](https://expedia.ca/Augusta-Hotels-Quality-Inn-Suites-Evergreen-Hotel.h787572.Hotel-Information) ![Best Western Plus Augusta Civic Center Inn](https://images.trvl-media.com/lodging/1000000/20000/12400/12303/ba6e7f89_y.jpg) ### Best Western Plus Augusta Civic Center Inn 10/10 Excellent "Room was spotless, staff very welcoming thank you guys " [](https://expedia.ca/Augusta-Hotels-Best-Western-Plus-Augusta-Civic-Center-Inn.h12303.Hotel-Information) ![Lockwood Hotel](https://images.trvl-media.com/lodging/79000000/78100000/78095000/78094968/d4c480e1_y.jpg) ### Lockwood Hotel 10/10 Excellent "The hotel is beautiful, staff is very accommodating and friendly, bed is very comfortable, room was spotless and inviting, right on a little downtown with restaurants in a block or two and also an upscale restaurant right inside the hotel 10 out of 10 would go again " [](https://expedia.ca/Waterville-Hotels-Lockwood-Hotel.h78094968.Hotel-Information) ![Fireside Inn & Suites Waterville](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg) ### Fireside Inn & Suites Waterville 10/10 Excellent "Efficient check in. Clean room, all toiletries and coffee for the morning." [](https://expedia.ca/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information) ![Senator Inn & Spa](https://images.trvl-media.com/lodging/1000000/10000/9900/9853/19df0ad9_y.jpg) ### Senator Inn & Spa 10/10 Excellent "Pleasant front desk check in " [](https://expedia.ca/Augusta-Hotels-Senator-Inn-Spa.h9853.Hotel-Information) ![Days Inn by Wyndham Augusta](https://images.trvl-media.com/lodging/1000000/60000/50600/50552/6adf084b_y.jpg) ### Days Inn by Wyndham Augusta 10/10 Excellent "I was on a business trip. I arrived late because of a snow storm and the person checking me in was very nice and friendly, taking the time to see that I could get to my room and not get lost. Checkout the next morning was quick and easy. That person checking me out again was very friendly and helpful. My only complaint about the cleanliness wasn't to do with my room, but the hall carpeting could use a good cleaning or maybe even replacement." [](https://expedia.ca/Augusta-Hotels-Days-Inn-By-Wyndham-Augusta.h50552.Hotel-Information) ![Sister A-Frame in Woods B](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/a00de8ac_y.jpg) ### Sister A-Frame in Woods B 10/10 Excellent "My stay in Oakland was perfect! I was looking forward to a quiet, peaceful retreat before Thanksgiving. The cabin was the perfect cozy place I needed to recharge. The place was clean. The hosts were responsive. I would strongly recommend." [](https://expedia.ca/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information) ## Find out more about Oakland ## Oakland Guest Houses information | Number of reviews | 14 | | ----------------- | -------------- | | Accommodation | 2 Guest Houses | | Lowest Price | CA $372 | | Highest Price | CA $372 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Capsule Hotels in Bar Harbor ](https://www.expedia.ca/Bar-Harbor-Capsule-Hotels.d561-aaCapsuleHotels.Travel-Guide-Accommodation) - [Farmstay in Belgrade ](https://www.expedia.ca/Belgrade-Agritourism.d6181917-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Belgrade ](https://www.expedia.ca/Belgrade-Apart-Hotels.d6181917-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Belgrade ](https://www.expedia.ca/Belgrade-Bed-And-Breakfast.d6181917-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Belgrade ](https://www.expedia.ca/Belgrade-Guest-Houses.d6181917-aaGuestHouses.Travel-Guide-Accommodation) - 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