Oakland, Maine

Vacation Rentals in Oakland, Maine

Discover 25 vacation rental properties in Oakland. From 1 to 6 bedrooms. Average $298/night. 100% have pools.

25 verified listings Book securely on VRBO Prices updated March 2026

25 properties available

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

1 bed 1 bath
PoolA/CWiFiBalcony
$116/night
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Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

2 beds 1 bath
PoolA/CWiFiBalcony
$279/night
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Sister A Frame in the Woods

Sister A Frame in the Woods

1 bed 1 bath
PoolA/CWiFiBalcony
$188/night
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Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake

Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake

3 beds 1 bath
PoolA/CWiFiBalcony
$170/night
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Quiet, 6 bedroom Lakefront home with private sandy beach, near Colby College

Quiet, 6 bedroom Lakefront home with private sandy beach, near Colby College

6 beds 3 baths
PoolA/CWiFiBalcony
$753/night
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Lavender Haze Cottage in the Woods

Lavender Haze Cottage in the Woods

1 bed 1 bath
PoolA/CWiFiBalcony
$109/night
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Lake Front with Amazing Sunsets on McGrath Pond

Lake Front with Amazing Sunsets on McGrath Pond

4 beds 2 baths
PoolA/CWiFiBalcony
$348/night
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Belgrade Lakes McGrath Pond

Belgrade Lakes McGrath Pond

3 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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Cozy Maine Lakefront Cabin near Colby College

Cozy Maine Lakefront Cabin near Colby College

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College

Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College

1 bed 1 bath
PoolA/CWiFiBalcony
$164/night
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Lakefront home near Colby College and Thomas College

Lakefront home near Colby College and Thomas College

5 beds 3 baths
PoolA/CWiFiBalcony
$738/night
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Belgrade lakes waterfront on Messalonskee 4 bedroom cabin

Belgrade lakes waterfront on Messalonskee 4 bedroom cabin

4 beds 1 bath
PoolA/CWiFiBalcony
$509/night
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Sunny, spacious and updated lake cottage - amazing views & steps from the water!

Sunny, spacious and updated lake cottage - amazing views & steps from the water!

6 beds 3 baths
PoolA/CWiFiBalcony
$702/night
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Lakefront home w/Dock & Fire Pit + Pet Friendly

Lakefront home w/Dock & Fire Pit + Pet Friendly

2 beds 1 bath
PoolA/CWiFiBalcony
$304/night
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Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes

Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

1 bath
PoolA/CWiFiBalcony
$174/night
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Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

2 beds
PoolA/CWiFiBalcony
$265/night
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Quaint Oakland Getaway on East Pond Lake!

Quaint Oakland Getaway on East Pond Lake!

1 bed 1 bath
PoolA/CWiFiBalcony
$169/night
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Quaint Little Cottage

Quaint Little Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$193/night
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Oakland Apt on Messalonskee Lake w/ Dock Access!

Oakland Apt on Messalonskee Lake w/ Dock Access!

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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The Modern Maine Retreat

The Modern Maine Retreat

4 beds 3 baths
PoolA/CWiFiBalcony
$226/night
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Lakefront Maine House ~ 4 Mi to Colby College

Lakefront Maine House ~ 4 Mi to Colby College

4 beds 1 bath
PoolA/CWiFiBalcony
$328/night
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Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

3 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Lakefront Oakland Vacation Rental w/ Dock + Views!

Lakefront Oakland Vacation Rental w/ Dock + Views!

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

3 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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More destinations in Maine

Old Orchard Beach (413) Wells (400) Bar Harbor (311) York (302) Portland (294) Ogunquit (254) Kennebunkport (216) Boothbay Harbor (206) Southwest Harbor (199) Kennebunk (199) Newry (192) Ellsworth (136) Scarborough (132) camden (105) Greenville (104) Harpswell (97) Mount Desert (96) Bethel (94) Mt Desert (64) Boothbay (63)