Title: Oakland Vacation Rentals from $299: Search Short-Term Rentals | Expedia.com

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![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

![](https://images.trvl-media.com/place/183294/94640f69-e5f6-46b9-9d25-cbf58ad86730.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=140470&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=140470&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=140470&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=140470&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Oakland vacation rentals

![Exterior](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/a00de8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/2d52a61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/c86c7808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/b1aad0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sister A-Frame in Woods B

[](https://www.expedia.com/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information)

Oakland

10/10

Exceptional

(9 reviews)

"Great stay. Would stay here again if in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda M.

$225 nightly

$245 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71940000/71931500/71931488/w750h562x0y386-23d53191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71940000/71931500/71931488/de4736c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/72000000/71940000/71931500/71931488/ea58fe6a.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/72000000/71940000/71931500/71931488/f8285adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central Maine Apartment offering 4 Seasons of Fun.

[](https://www.expedia.com/Oakland-Hotels-Central-Maine-Apartment-Offering-4-Seasons-Of-Fun.h71931488.Hotel-Information)

Oakland

10/10

Exceptional

(43 reviews)

"Great hiking - nice views."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Norbert A.

$221 nightly

$241 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Central-Maine-Apartment-Offering-4-Seasons-Of-Fun.h71931488.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/ea4831c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/445432e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/682fc57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/43a37948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The heart of the Belgrade Lakes 

[](https://www.expedia.com/Oakland-Hotels-The-Heart-Of-The-Belgrade-Lakes.h107166584.Hotel-Information)

Oakland

9.0/10

Wonderful

(9 reviews)

"Host was very accommodating "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maureen

$176 nightly

$191 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-The-Heart-Of-The-Belgrade-Lakes.h107166584.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/4b703bf0.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)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/17a87d2f.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/b51d7b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy getaway: farmhouse with wood stove & jacuzzi tub

[](https://www.expedia.com/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information)

Oakland

10/10

Exceptional

(9 reviews)

"It was that was said to be The host was very nice and helpful . I enjoyed my stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea C.

$334 nightly

$355 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/1d81fc0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/02a26a70_edited_16e3.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)

![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)

### Discover Oakland charm near Colby College 10 min

[](https://www.expedia.com/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information)

Oakland

10/10

Exceptional

(6 reviews)

"Very clean and comfy. A pleasure to stay there. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Vicki W.

$236 nightly

$257 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/2106c4ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/f5af8f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/b382c1a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/e8e22159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

[](https://www.expedia.com/Oakland-Hotels-NEW-Cozy-Cabin-Located-In-Oakland-Tucked-Away-In-A-Peaceful-Wooded-Scene.h118481811.Hotel-Information)

Oakland

$270 nightly

$294 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-NEW-Cozy-Cabin-Located-In-Oakland-Tucked-Away-In-A-Peaceful-Wooded-Scene.h118481811.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/f312599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/38840bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/0e7387ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/df06a28f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cabin Skowhegan

[](https://www.expedia.com/Skowhegan-Hotels-Free-Private-Parking.h76995336.Hotel-Information)

Skowhegan

9.8/10

Exceptional

(51 reviews)

"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sue

$193 nightly

$210 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Skowhegan-Hotels-Free-Private-Parking.h76995336.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/8e06d5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/75c4bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/7cac22ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/77cd3017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two bedroom Mid Century Modern apartment in Downtown Hallowell

[](https://www.expedia.com/Augusta-Hotels-Two-Bedroom-Mid-Century-Modern-Apartment-In-Downtown-Hallowell.h33954758.Hotel-Information)

Hallowell

10/10

Exceptional

(82 reviews)

"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rebekah B.

$211 nightly

$230 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-Two-Bedroom-Mid-Century-Modern-Apartment-In-Downtown-Hallowell.h33954758.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/515b6a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/effc1142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/2088d126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/576b2944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cabin in the birches right on the atv trail!

[](https://www.expedia.com/Fairfield-Hotels-Charming-Cabin-In-The-Birches-Right-On-The-Atv-Trail.h107715523.Hotel-Information)

Fairfield

9.0/10

Wonderful

(6 reviews)

"Very neat cabin. Spacious all utilities and a fire pit"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa O.

$182 nightly

$198 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Fairfield-Hotels-Charming-Cabin-In-The-Birches-Right-On-The-Atv-Trail.h107715523.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/6636bd76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/d3ba341c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/9da55179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/67387a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Angel Mist Retreat Garage Apartment

[](https://www.expedia.com/Pittsfield-Hotels-Welcome-To-Angel-Mist-Retreat.h89759088.Hotel-Information)

Pittsfield

10/10

Exceptional

(14 reviews)

"Great stay. Very comfortable, roomy, clean and good overall value."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rob K.

$283 nightly

$309 total

Feb 13 - Feb 14

Total with taxes and fees

[](https://www.expedia.com/Pittsfield-Hotels-Welcome-To-Angel-Mist-Retreat.h89759088.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/82000000/81920000/81916300/81916204/17014025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/82000000/81920000/81916300/81916204/37656f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81920000/81916300/81916204/72956d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/82000000/81920000/81916300/81916204/577bfe71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths

[](https://www.expedia.com/Madison-Hotels-Gorgeous-Cabin-On-20-Acres.h81916204.Hotel-Information)

Madison

10/10

Exceptional

(42 reviews)

"Everything was amazing"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Antwan B.

$343 nightly

$374 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Gorgeous-Cabin-On-20-Acres.h81916204.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/3d25364d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/d71068b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/c6360210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/71b4e138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ice Fishing, Dog Friendly, Lake Great Pond

[](https://www.expedia.com/Belgrade-Hotels-NEW-Cozy-3-Bedroom-Cottage-On-Great-Pond-Dog-Friendly.h76964979.Hotel-Information)

Belgrade

10/10

Exceptional

(49 reviews)

"All was exactly as we hoped it would be, perfect for a family and added benefit of pet friendly."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan I.

$274 nightly

$299 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/Belgrade-Hotels-NEW-Cozy-3-Bedroom-Cottage-On-Great-Pond-Dog-Friendly.h76964979.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/4c3bafc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/d59c99fb.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)

![Interior](https://images.trvl-media.com/lodging/116000000/115930000/115923400/115923334/14681d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

[](https://www.expedia.com/Madison-Hotels-Charming-1-Bedroom-Building-With-WiFi.h115923334.Hotel-Information)

Madison

9.0/10

Wonderful

(4 reviews)

"Excellent service and perfect for our stay. Would book again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

$155 nightly

$169 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Charming-1-Bedroom-Building-With-WiFi.h115923334.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/96000000/95770000/95768400/95768356/0cbbebb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95770000/95768400/95768356/dc34d98d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95770000/95768400/95768356/7447dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95770000/95768400/95768356/d8ac233a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Retreat- A Relaxing Beachside Bungalow

[](https://www.expedia.com/Burnham-Hotels-The-Retreat-A-Relaxing-Beachside-Bungalow.h95768356.Hotel-Information)

Burnham

10/10

Exceptional

(3 reviews)

"Great cabin and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John V.

$375 nightly

$409 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Burnham-Hotels-The-Retreat-A-Relaxing-Beachside-Bungalow.h95768356.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)

![Smart TV](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/acce8344.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)

![Property grounds](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/f0524dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage on water's edge of Lake Cobbosseecontee

[](https://www.expedia.com/Manchester-Hotels-Cozy-Cottage-On-Waters-Edge-Of-Lake-Cobbosseecontee.h57698782.Hotel-Information)

Manchester

8.8/10

Excellent

(19 reviews)

"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie P.

$309 nightly

$337 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Manchester-Hotels-Cozy-Cottage-On-Waters-Edge-Of-Lake-Cobbosseecontee.h57698782.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113680000/113678100/113678032/c263b34d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/114000000/113680000/113678100/113678032/0316cfb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113680000/113678100/113678032/0844031e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113680000/113678100/113678032/8805d82a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious King Room with AC, WiFi in Peaceful Wilton

[](https://www.expedia.com/Wilton-Hotels-Large-King-Room.h113678032.Hotel-Information)

wilton

$198 nightly

$216 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Wilton-Hotels-Large-King-Room.h113678032.Hotel-Information)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/89000000/88920000/88914700/88914690/edd2c5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/89000000/88920000/88914700/88914690/222611f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88920000/88914700/88914690/e33a9b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower](https://images.trvl-media.com/lodging/89000000/88920000/88914700/88914690/c7495d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious modern living in a quite neighborhood

[](https://www.expedia.com/Madison-Hotels-Spacious-Modern-Living-In-A-Quite-Neighborhood.h88914690.Hotel-Information)

Madison

$145 nightly

$158 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Spacious-Modern-Living-In-A-Quite-Neighborhood.h88914690.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/0450d353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/d8ba6715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/2e3e136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/3ff0e36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lighthouse Lane

[](https://www.expedia.com/Augusta-Hotels-Cottage-On-Cobbosseecontelake.h63112739.Hotel-Information)

Manchester

10/10

Exceptional

(70 reviews)

"Very nice stay Beautiful lake views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen G.

$286 nightly

$312 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-Cottage-On-Cobbosseecontelake.h63112739.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/815a3cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/w1188h800x0y0-be52bc8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, offices](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/a13047f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/73ce4a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family's Paradise: 3BR/2BA,Game Room & Lake Access

[](https://www.expedia.com/Belgrade-Hotels-A-Familys-Paradise-Spacious-3BR2BA-W-Game-Room.h105754901.Hotel-Information)

Belgrade

9.8/10

Exceptional

(9 reviews)

"We enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyson W.

$740 nightly

$807 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Belgrade-Hotels-A-Familys-Paradise-Spacious-3BR2BA-W-Game-Room.h105754901.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/w3024h3351x0y0-28e12c91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/aa47261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/3a4f8cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/80750082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

[](https://www.expedia.com/Whitefield-Hotels-Studio-Apt-100-Acres-With-KayakCanoePaddleboards.h103899892.Hotel-Information)

Whitefield

10/10

Exceptional

(6 reviews)

"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sandra L.

$250 nightly

$273 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Whitefield-Hotels-Studio-Apt-100-Acres-With-KayakCanoePaddleboards.h103899892.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.com/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22&regionId=140470&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maine%2C+United+States+of+America&regionId=140470&latLong=44.540222%2C-69.721992&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

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## Top Oakland Hotel Reviews

![Holiday Inn Express & Suites Waterville - North by IHG](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3_y.jpg)

### Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent

"The rokm was great and very clean. The staff was awesome. "

[](https://expedia.com/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.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

"The room was clean and staff accommodating. When we had to leave immediately due to the storm overtaking the area, they cancelled the remainder of our reservation without a fuss."

[](https://expedia.com/Augusta-Hotels-Days-Inn-By-Wyndham-Augusta.h50552.Hotel-Information)

![Best Western Plus Waterville Grand Hotel](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/c76e225a_y.jpg)

### Best Western Plus Waterville Grand Hotel

10/10 Excellent

"Breakfast was excellent. All staff were nice, acknowledged your presence, were very accommodating. Was very thankful. Sone if tge reviews online discouraged me. Was thankful the room I had was clean, staff was great!"

[](https://expedia.com/Augusta-Hotels-Best-Western-Plus-Waterville-Grand-Hotel.h22003.Hotel-Information)

![Hampton Inn Augusta](https://images.trvl-media.com/lodging/6000000/5190000/5185100/5185016/bf2caaca_y.jpg)

### Hampton Inn Augusta

10/10 Excellent

"Friendly staff very clean room cozy beds and breakfast in morning was an added bonus. "

[](https://expedia.com/Augusta-Hotels-Hampton-Inn-Augusta.h5185016.Hotel-Information)

![Charming Guest House on Farm - Pets Welcome](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/4b703bf0_y.jpg)

### Charming Guest House on Farm - Pets Welcome

10/10 Excellent

"It was a great stay. The house is very comfortable"

[](https://expedia.com/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information)

![Comfort Inn & Suites Wilton](https://images.trvl-media.com/lodging/3000000/2120000/2113200/2113105/0cd9da98_y.jpg)

### Comfort Inn & Suites Wilton

10/10 Excellent

"Early check in wasn’t a problem. "

[](https://expedia.com/Augusta-Hotels-Comfort-Inn-And-Suites-Wilton.h2113105.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

"Room clean, comfortable, and had a great reading chair!"

[](https://expedia.com/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

"Quiet and clean room. Very Good Breakfast."

[](https://expedia.com/Augusta-Hotels-Best-Western-Plus-Augusta-Civic-Center-Inn.h12303.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

"Nice clean room, cozy, friendly staff, fair price, convenient location. "

[](https://expedia.com/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information)

## Find out more about Oakland

**Everything you need to know about Oakland vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Oakland vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $299 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Oakland rentals**

At Expedia, we put the best Oakland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Oakland ](https://expedia.com/Oakland-Private-Vacation-Homes.d140470-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Oakland ](https://expedia.com/Oakland-Cottages.d140470-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Oakland ](https://expedia.com/Oakland-Cabins.d140470-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Oakland ](https://expedia.com/Oakland-Apartments.d140470-aaApartments.Travel-Guide-Accommodation)
- [Motels in Oakland ](https://expedia.com/Oakland-Motels.d140470-aaMotels.Travel-Guide-Accommodation)
- [Chalets in Oakland ](https://expedia.com/Oakland-Chalets.d140470-aaChalets.Travel-Guide-Accommodation)
- [Resorts in Oakland ](https://expedia.com/Oakland-Resorts.d140470-aaResorts.Travel-Guide-Accommodation)
- [Farmstay in Oakland ](https://expedia.com/Oakland-Agritourism.d140470-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Oakland ](https://expedia.com/Oakland-Bed-And-Breakfast.d140470-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Oakland ](https://expedia.com/Oakland-Guest-Houses.d140470-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Oakland ](https://expedia.com/Oakland-Villas.d140470-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Oakland ](https://expedia.com/Oakland-Lodges.d140470-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Oakland ](https://expedia.com/Oakland-Apart-Hotels.d140470-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Oakland ](https://expedia.com/Oakland-RV-Parks.d140470-aaRVParks.Travel-Guide-Accommodation)
- [Condo Rentals in Oakland ](https://expedia.com/Oakland-Condos.d140470-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Oakland?

### What are some of the best vacation rentals in Oakland?

### How many vacation rentals will I find in Oakland?

### What can I see and do in Oakland?

### What are vacation rentals like in Oakland?

### Expedia's Latest Trends

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- [Hotels in Wells](https://expedia.com/Wells-Hotels.d56045.Travel-Guide-Hotels)
- [Hotels in Old Orchard Beach](https://expedia.com/Old-Orchard-Beach-Hotels.d9256.Travel-Guide-Hotels)
- [Oceanfront Hotels in York Beach](https://expedia.com/York-Beach-Hotels-Oceanfront-Hotels.0-0-d183307-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Freeport](https://expedia.com/Freeport-Hotels.d180773.Travel-Guide-Hotels)
- [Cheap Hotels in Portland](https://expedia.com/Portland-Hotels-Cheap-Hotels.0-0-d181420-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Augusta](https://expedia.com/Augusta-Hotels.d452.Travel-Guide-Hotels)
- [Hotels in South Portland](https://expedia.com/South-Portland-Hotels.d6769.Travel-Guide-Hotels)
- [Hotels in Rockland](https://expedia.com/Rockland-Hotels.d3004.Travel-Guide-Hotels)
- [Hotels in Belfast](https://expedia.com/Belfast-Hotels.d55056.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Bangor](https://expedia.com/Cheap-Flights-To-Bangor.d6050918.Travel-Guide-Flights)
- [Cheap Flights to Portland](https://expedia.com/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights)
- [Cheap Flights to Bar Harbor](https://expedia.com/Cheap-Flights-To-Bar-Harbor.d561.Travel-Guide-Flights)

Cars

- [Car rentals in Bangor](https://expedia.com/Car-Rentals-In-Bangor.d6050918.Car-Rental-Guide)
- [Car rentals in Portland](https://expedia.com/Car-Rentals-In-Portland.d181420.Car-Rental-Guide)

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