Home Vacation Rentals By Owner In Oakland, ME

Showing 20 Of 65 Vacation Rentals
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Exceptional(28)

$240.01

/ Nightly
Cabin

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

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(26)

$734.66

/ Nightly
Private Vacation Home

Lake Front with Amazing Sunsets on McGrath Pond

Oakland, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(22)

$362.4

/ Nightly
Private Vacation Home

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

Rome, Maine, United States

Bed 2

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(29)

$380.3

/ Nightly
Private Vacation Home

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

Rome, Maine, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(3)

$401.9

/ Nightly
Cabin

Cozy Maine Lakefront Cabin near Colby College

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$170.15

/ Nightly
Apartment

Sunny, Spacious, and Centrally Located

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(19)

$617.76

/ Nightly
Cabin

Belgrade Lakes McGrath Pond

Oakland, Maine, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(15)

$734.44

/ Nightly
Cabin

The Map House - Western facing updated fishing cabin on Long Pond lake

Rome, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(11)

$657

/ Nightly
Private Vacation Home

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Oakland, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$519.46

/ Nightly
Cottage

Great Pond, Four bedroom cottage in Windover.

Rome, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(8)

Select Dates for Price
Cottage

Charming 1920's lakefront cottage on Great Pond, sunsets from the dock

Rome, Maine, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps
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$113.11

/ Nightly
Cabin

3-bedroom cabin in terrific Rome with access to Great Pond

Rome, Maine, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$826.5

/ Nightly
Private Vacation Home

Beautiful year round home located on McGrath Pond

Oakland, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(18)

$253.97

/ Nightly
Private Vacation Home

Discover Oakland charm near Colby College 10 min

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(7)

$352.07

/ Nightly
Cabin

Lakefront camp on Great Pond

Rome, Maine, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(11)

$235.44

/ Nightly
Apartment

The heart of the Belgrade Lakes

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(29)

$284.54

/ Nightly
Guest House

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

Oakland, Maine, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$632.36

/ Nightly
Cottage

Belgrade lakes waterfront on Messalonskee 4 bedroom cabin

Oakland, Maine, United States

Bed 4

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Select Dates for Price
Private Vacation Home

Inviting Lakeside Home with direct dock access, patio seating, and gas fireplace

Rome, Maine, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(17)

$351.6

/ Nightly
Cabin

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

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Private vacation home

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View 27 Private vacation home

Home Most popular vacation rentals in Oakland

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Exceptional(17)

$273.64

/ Nightly
Guest house

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

Oakland, Maine, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(17)

$331.91

/ Nightly
Cabin

Lakefront camp on Great Pond

Rome, Maine, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(17)

$324.82

/ Nightly
Cabin

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

Rome, Maine, United States

Bed 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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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 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(17)

$322.02

/ Nightly
Cottage

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

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$299.75

/ Nightly
Cabin

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

Oakland, Maine, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$292.12

/ Nightly
Cabin

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

Oakland, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(17)

$241.98

/ Nightly
Apartment

Central Maine Apartment offering 4 Seasons of Fun.

Oakland, Maine, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(17)

$244.49

/ Nightly
Cabin

Sister A Frame in the Woods

Oakland, Maine, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$251.35

/ Nightly
Cabin

Sister A-Frame in Woods B

Oakland, Maine, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps

Most Popular Cities in Maine