Title: Oakland Vacation Home Rentals from CA $221: Search Top Private Vacation Homes for Rent | 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) ![](https://mediaim.expedia.com/destination/2/05f2f66360ab97fbc8a6b8b59f2f2a24.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marc Maheu # Oakland Vacation Rentals ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=140470&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Oakland Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/a9427e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/31ceecc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/c8d60c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/e447dc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming historic guest house on farm 3 bedrooms wood stove pet friendly Oakland 10/10 Exceptional (7) "Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! " CA $299 CA $494 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/5d63eee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/24687d8e_edited_120b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/2be335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/1d81fc0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Discover Oakland charm near Colby College 10 min Oakland 10/10 Exceptional (4) "New, clean and had everything we needed. " CA $128 CA $362 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/fb55cac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/587c3b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/028ea602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121270000/121269300/121269271/262abcab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### My Valhalla Farm Oakland CA $396 CA $572 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Oakland-Hotels-My-Valhalla-Farm.h121269271.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/e0ffec4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/27f2044c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/2dd0dee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/a67fe484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine Madison 10/10 Exceptional (3) "Excellent service and perfect for our stay. Would book again!" CA $175 CA $221 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Madison-Hotels-Charming-1-Bedroom-Building-With-WiFi.h115923334.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/83000000/82720000/82715500/82715456/effd6d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82720000/82715500/82715456/3786b4c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82720000/82715500/82715456/87c98e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82720000/82715500/82715456/8f62b755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Country Home w/ Hot Tub, near Colby/Thomas Sidney 9.8/10 Exceptional (29) "Wonderful location and beautiful property, very peaceful and convenient " [](https://www.expedia.ca/Sidney-Hotels-Full-Home.h82715456.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/129d87e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/5c8b3b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/db1800b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/37c037db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage on water's edge of Lake Cobbosseecontee Manchester 8.8/10 Excellent (16) "Perfect old fashion Maine cottage! Great sunsets!" CA $183 CA $447 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Manchester-Hotels-Cozy-Cottage-On-Waters-Edge-Of-Lake-Cobbosseecontee.h57698782.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/58ab669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/ea1002ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/9157f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/64d8bcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3350 Middle Road Sidney 8.0/10 Very good (3) "A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table" CA $386 CA $482 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Augusta-Hotels-The-Maine-Experience-Where-Expansive-Nature-Meets-Modern-Comfort.h118939094.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/b6073572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/d65eda33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/f5af7b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113970000/113961400/113961345/eeafa7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly Canaan 10/10 Exceptional (3) "Great spot on the lake! The house was super clean, beds were very comfortable, kitchen was well stocked and had everything we needed while we were there. The neighbor's house is really close to the property along the shared beach, and while it was never an issue for us, you may hear the neighbors as they come and go from their house. Overall a fantastic stay." CA $207 CA $518 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Canaan-Hotels-3-Bedroom-Lakefront-Home-With-Beach-Front.h113961345.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42670000/42662400/42662330/2eb0bd4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42670000/42662400/42662330/a06aacf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42670000/42662400/42662330/8fa7ded6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42670000/42662400/42662330/fe08b545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Every window has a spectacular lake view Low fees Wayne 9.8/10 Exceptional (43) "Nice place. Plenty of space. Clean and all the amenities you could need " CA $378 CA $644 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Wayne-Hotels-Gorgeous-Lake-House.h42662330.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35270000/35267300/35267232/3bf59363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35270000/35267300/35267232/b07044eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35270000/35267300/35267232/1d2e2542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35270000/35267300/35267232/4d1cf8c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A soul soothing escape. Artistically built and lovingly maintained. New Sharon 10/10 Exceptional (29) "We loved the property. The Views are great and it is very comfortable and quiet. I would highly recommend staying here." CA $353 CA $585 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/New-Sharon-Hotels-A-Soul-Soothing-Escape-Artistically-Built-And-Lovingly-Maintained.h35267232.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99340000/99335200/99335199/091ffe94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99340000/99335200/99335199/88420d20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99340000/99335200/99335199/edad25ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/100000000/99340000/99335200/99335199/78cf9552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Lakefront Home: Big Porches, Kayaks & Room to Gather Winthrop 9.6/10 Exceptional (4) "Wonderful stay! This is the third year in a row our group of "mature" fishermen have stayed at this lake. This was by far the best place we stayed at. Views and setting are all that we could ask for. We'll be back again." CA $410 CA $947 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winthrop-Hotels-Historic-Lake-Front-Home-On-Cobbosseeconte-Lake.h99335199.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=2025-10-26&endDate=2025-10-27®ionId=140470&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d140470-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Private-Vacation-Homes.d140470-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Oakland Hotel Reviews ![Super 8 by Wyndham Augusta](//images.trvl-media.com/lodging/1000000/460000/459700/459673/623a5000_y.jpg) ### Super 8 by Wyndham Augusta 10/10 Excellent "Consider offering cold water at breakfast. Otherwise it was a great stay - just what I wanted" [](https://expedia.ca/Augusta-Hotels-Super-8-By-Wyndham-Augusta.h459673.Hotel-Information) ![Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes](//images.trvl-media.com/lodging/62000000/61510000/61508300/61508289/569b4e0b_y.jpg) ### Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes 10/10 Excellent "An excellent location and very enjoyable setting on the pond. Great place to sit outside and enjoy coffee in the morning and a glass of wine in the evening." [](https://expedia.ca/Augusta-Hotels-Get-Away-From-It-All-At-This-Cottage-On-East-Pond-In-Oakland-Maine.h61508289.Hotel-Information) ![Comfort Inn & Suites Wilton](//images.trvl-media.com/lodging/3000000/2120000/2113200/2113105/0cd9da98_y.jpg) ### Comfort Inn & Suites Wilton 10/10 Excellent "Great place to stay on our fall color trip " [](https://expedia.ca/Augusta-Hotels-Comfort-Inn-And-Suites-Wilton.h2113105.Hotel-Information) ![Days Inn by Wyndham Augusta](//images.trvl-media.com/lodging/1000000/60000/50600/50552/6adf084b_y.jpg) ### Days Inn by Wyndham Augusta 10/10 Excellent "Our tv would not work. Texted with front desk who told us what to try. Still did not work and when notified they came up and fixed it! Well done! Quiet stay- would stay again! Didn’t care much for the continental breakfast offered so we passed and stopped elsewhere" [](https://expedia.ca/Augusta-Hotels-Days-Inn-By-Wyndham-Augusta.h50552.Hotel-Information) ![Holiday Inn Express & Suites Waterville - North by IHG](//images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3_y.jpg) ### Holiday Inn Express & Suites Waterville - North by IHG 10/10 Excellent "Friendly and courteous staff. Very helpful with dining locations. Would recommend a lounge/pub setting to enjoy a drink after a long traveling day. Excellent hotel!!! " [](https://expedia.ca/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.Hotel-Information) ![The Skowhegan By Kasa](//images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/f4aad0c9_y.jpg) ### The Skowhegan By Kasa 10/10 Excellent "Great room just needed a microwave" [](https://expedia.ca/Skowhegan-Hotels-The-Skowhegan-By-Kasa.h114717254.Hotel-Information) ![The Elmwood](//images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/6685e6ca_y.jpg) ### The Elmwood 10/10 Excellent "Perfect location, immediately off the highway. Clean, comfy room. Decent amenities. Friendly staff. Only complaint is that the breakfast options were slim,at best. Would I stay there again? Absolutely! Would I recommend them? Absolutely!" [](https://expedia.ca/Waterville-Hotels-The-Elmwood.h71555928.Hotel-Information) ![Maine Evergreen Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/790000/787600/787572/4f6988c8_y.jpg) ### Maine Evergreen Hotel, an Ascend Collection Hotel 10/10 Excellent "Nice stay nice people ! " [](https://expedia.ca/Augusta-Hotels-Quality-Inn-Suites-Evergreen-Hotel.h787572.Hotel-Information) ![Lakefront home on McGrath Pond - once featured on Maine Cabin Masters](//images.trvl-media.com/lodging/84000000/83820000/83816100/83816029/96158834_y.jpg) ### Lakefront home on McGrath Pond - once featured on Maine Cabin Masters 10/10 Excellent "Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. " [](https://expedia.ca/Oakland-Hotels-Lakefront-Home-On-McGrath-Pond-Once-Featured-On-Maine-Cabin-Masters.h83816029.Hotel-Information) ## Find out more about Oakland ## Oakland Vacation Homes information | Number of reviews | 138 | | --- | --- | | Accommodation | 127 Vacation Homes | | Lowest Price | CA $221 | | Highest Price | CA $947 | ## 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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