Vacation Home Rentals By Owner In Oakland, ME

Showing 20 Of 27 Vacation Rentals

Exceptional(29)

$380.3

/ Nightly

Private Vacation Home

Cozy Long Pond Cottage: community access, private mooring & shared dock.

Rome, Maine, United States

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Bath

Sleeps

Exceptional(66)

$1039.86

/ Nightly

Private Vacation Home

Quiet, 6 bedroom 4 bath Lakefront home, private sandy beach, near Colby College

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(38)

$1029.51

/ Nightly

Private Vacation Home

Lakefront home near Colby College and Thomas College

Oakland, Maine, United States

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Bath

Sleeps

$944.01

/ Nightly

Private Vacation Home

Peaceful Maine hideaway with lake views, pool table, dock access, and Wi-Fi

Rome, Maine, United States

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Bath

Sleeps

Exceptional(3)

$826.5

/ Nightly

Private Vacation Home

Beautiful year round home located on McGrath Pond

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(26)

$734.66

/ Nightly

Private Vacation Home

Lake Front with Amazing Sunsets on McGrath Pond

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(11)

$657

/ Nightly

Private Vacation Home

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(26)

$524.29

/ Nightly

Private Vacation Home

Belgrade Lakes, Great Pond - Sandy Entry & Quiet Cove

Rome, Maine, United States

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Bath

Sleeps

Exceptional(7)

$515.57

/ Nightly

Private Vacation Home

Lakeside Home on Great Pond in Belgrade Lakes with hot tub, walk to village.

Belgrade Lakes, Maine, United States

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Bath

Sleeps

Exceptional(6)

$471.37

/ Nightly

Private Vacation Home

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!

Rome, Maine, United States

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Bath

Sleeps

Exceptional(7)

$464.89

/ Nightly

Private Vacation Home

Lakefront Maine House ~ 4 Mi to Colby College

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(56)

$410.93

/ Nightly

Private Vacation Home

Beautiful Cottage In Wildewood Estates

Rome, Maine, United States

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Bath

Sleeps

$382.23

/ Nightly

Private Vacation Home

Cozy & Modern 2BR/2BA with Long Pond access in Rome

Rome, Maine, United States

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Bath

Sleeps

Exceptional(55)

$380.96

/ Nightly

Private Vacation Home

Classy AF Home Steps from Colby and Trails

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(6)

Select Dates for Price

Private Vacation Home

Classic Maine 3-bedroom steps from Great Pond, newly decorated, work or play!

Rome, Maine, United States

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Bath

Sleeps

Exceptional(22)

$373.87

/ Nightly

Private Vacation Home

4 br comfortable home near Belgrade Lakes

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(13)

$367.33

/ Nightly

Private Vacation Home

Waterfront Home Long Pond, Belgrade Lakes Maine

Rome, Maine, United States

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Bath

Sleeps

Exceptional(2)

$365.97

/ Nightly

Private Vacation Home

Charming Lakeview House with Deck, Cozy Fireplace and firepit

Rome, Maine, United States

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Bath

Sleeps

Exceptional(22)

$362.4

/ Nightly

Private Vacation Home

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Rome, Maine, United States

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Bath

Sleeps

Exceptional(17)

$355.69

/ Nightly

Private Vacation Home

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Oakland, Maine, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 27 Private vacation home

Most popular vacation rentals in Oakland

Exceptional(17)

$273.64

/ Nightly

Guest house

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(17)

$331.91

/ Nightly

Cabin

Lakefront camp on Great Pond

Rome, Maine, United States

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Bath

Sleeps

Exceptional(17)

$324.82

/ Nightly

Cabin

Charming lakefront cabin with large screened-in porch and lawn in Rome

Rome, Maine, United States

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Bath

Sleeps

Exceptional(17)

$322.09

/ Nightly

Private vacation home

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Oakland, Maine, United States

Bed

Bath

Sleeps

Exceptional(17)

$322.02

/ Nightly

Cottage

Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe

Oakland, Maine, United States

Bed

Bath

Sleeps

Exceptional(17)

$299.75

/ Nightly

Cabin

This Cozy Cabin is located in Oakland, tucked away in a peaceful wooded scene.

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(17)

$292.12

/ Nightly

Cabin

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

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(17)

$241.98

/ Nightly

Apartment

Central Maine Apartment offering 4 Seasons of Fun.

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(17)

$244.49

/ Nightly

Cabin

Sister A Frame in the Woods

Oakland, Maine, United States

Bed

Bath

Sleeps

Exceptional(17)

$251.35

/ Nightly

Cabin

Sister A-Frame in Woods B

Oakland, Maine, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Oakland, ME

$380.3

$1039.86

$1029.51

$944.01

$826.5

$734.66

$657

$524.29

$515.57

$471.37

$464.89

$410.93

$382.23

$380.96

$373.87

$367.33

$365.97

$362.4

$355.69

Rent a place that suits your needs

Most popular vacation rentals in Oakland

$273.64

$331.91

$324.82

$322.09

$322.02

$299.75

$292.12

$241.98

$244.49

$251.35

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