Oakland House Navigation Bar
Oakland House Logo
HOME COTTAGES THE INN ACORN GUEST HOUSE DINING WEDDINGS & EVENTS HISTORY ACTIVITIES CONTACT US
1-207-359-8521
The Oakland House
_
HOME COTTAGES THE INN Acorn GUEST HOUSE DINING WEDDINGS & EVENTS HISTORY ACTIVITIES CONTACT US
_
1-207-359-8521
LODGING AERIAL PHOTO DRIVING MAP RENTALS EXPERIENCES
0

Availability Calendar

for
×

Dates

Nights
Available
No Vacancy
Checkout IconCheckout
Continue or select a new check in date. Continue or Click any date in the future to extend your check out date.
Search
What dates will you be staying?

Guests

1 Adults, 0 Children
Adults
Children
×
Dates
1 Nights
∞
1 Nights
Apply
April 2025
SunMonTueWedThuFriSat
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Select a check out date or click check in to select a new check in date
Apply

Dates

-- Nights
April 2025
SunMonTueWedThuFriSat
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Available
No Vacancy
Checkout IconCheckout
Continue or select a new check in date. Continue or Click any date in the future to extend your check out date.
Filter
Map View
Show All
Cottages /Inn room 0 Available
Cottage Rentals 0 Available
Dog-friendly Cottage 0 Available
2BR King/Queen Room in Main Inn 0 Available
Acorn Guest House 0 Available
Show All
Cottages /Inn room 0 Available
Cottage Rentals 0 Available
Dog-friendly Cottage 0 Available
2BR King/Queen Room in Main Inn 0 Available
Acorn Guest House 0 Available
Sign up for our newsletter
Be among the first to know about our specials and promotions
Your information is secure and confidential (more details)
Applied Filters
Thursday Apr 3, 2025 - Friday Apr 4, 2025 - 1 Adults. Showing 21 results.
Image 1 for Weekly Discount
Only 2 left

Weekly Discount

Stay for 6 nights and get 1 weekend night for free!
Package Details
Image 1 for MONHEGAN SUITE Image 2 for MONHEGAN SUITE Image 3 for MONHEGAN SUITE Image 4 for MONHEGAN SUITE Image 5 for MONHEGAN SUITE Image 6 for MONHEGAN SUITE Image 7 for MONHEGAN SUITE Image 8 for MONHEGAN SUITE
1 / 8
Image 1 for MONHEGAN SUITEImage 2 for MONHEGAN SUITEImage 3 for MONHEGAN SUITEImage 4 for MONHEGAN SUITEImage 5 for MONHEGAN SUITEImage 6 for MONHEGAN SUITEImage 7 for MONHEGAN SUITEImage 8 for MONHEGAN SUITE
Pet Friendly

MONHEGAN SUITE

On the second floor of the historic inn, this large two-bedroom corner suite with king and queen beds plus a pull-out sofa is ideal for families up to six people and includes...
More Details Calendar
Image 1 for NORTH HAVEN SUITE Image 2 for NORTH HAVEN SUITE Image 3 for NORTH HAVEN SUITE Image 4 for NORTH HAVEN SUITE Image 5 for NORTH HAVEN SUITE
1 / 5
Image 1 for NORTH HAVEN SUITEImage 2 for NORTH HAVEN SUITEImage 3 for NORTH HAVEN SUITEImage 4 for NORTH HAVEN SUITEImage 5 for NORTH HAVEN SUITE
Pet Friendly

NORTH HAVEN SUITE

On the second floor of the historic inn, this two room corner suite with a king bed plus a pull-out sofa is ideal for families of up to four people and includes a private bat...
More Details Calendar
Image 1 for LITTLE DEER Image 2 for LITTLE DEER Image 3 for LITTLE DEER Image 4 for LITTLE DEER Image 5 for LITTLE DEER
1 / 5
Image 1 for LITTLE DEERImage 2 for LITTLE DEERImage 3 for LITTLE DEERImage 4 for LITTLE DEERImage 5 for LITTLE DEER
Pet Friendly

LITTLE DEER

On the second floor of the historic inn, this front-of-the-inn bedroom has a full bed and ocean view facing Little Deer Isle. It has a private bath with tub/shower and sleeps...
More Details Calendar
Image 1 for BLUE HILL Image 2 for BLUE HILL Image 3 for BLUE HILL Image 4 for BLUE HILL Image 5 for BLUE HILL Image 6 for BLUE HILL
1 / 6
Image 1 for BLUE HILLImage 2 for BLUE HILLImage 3 for BLUE HILLImage 4 for BLUE HILLImage 5 for BLUE HILLImage 6 for BLUE HILL
Pet Friendly

BLUE HILL

On the second floor of the historic 175-year-old-inn, this queen bedroom with pull-out twin sofa bed, tucked away in the quiet Northwest wing, has a partial ocean view and ba...
More Details Calendar
Image 1 for ISLESBORO Image 2 for ISLESBORO Image 3 for ISLESBORO Image 4 for ISLESBORO Image 5 for ISLESBORO
1 / 5
Image 1 for ISLESBOROImage 2 for ISLESBOROImage 3 for ISLESBOROImage 4 for ISLESBOROImage 5 for ISLESBORO
Pet Friendly

ISLESBORO

Located on the third floor of the newly renovated historic inn, this beautiful corner queen suite with garden views has private bath with glass stall shower.

166 square fe...
More Details Calendar
Image 1 for CAMDEN HILLS SUITE Image 2 for CAMDEN HILLS SUITE Image 3 for CAMDEN HILLS SUITE Image 4 for CAMDEN HILLS SUITE Image 5 for CAMDEN HILLS SUITE
1 / 5
Image 1 for CAMDEN HILLS SUITEImage 2 for CAMDEN HILLS SUITEImage 3 for CAMDEN HILLS SUITEImage 4 for CAMDEN HILLS SUITEImage 5 for CAMDEN HILLS SUITE
Pet Friendly

CAMDEN HILLS SUITE

Located on the third floor of the historic inn, this spacious loft-like honeymoon suite is oriented for spectacular sunset and island views over the Camden Hills and Deer Isl...
More Details Calendar
Image 1 for STONINGTON Image 2 for STONINGTON Image 3 for STONINGTON Image 4 for STONINGTON Image 5 for STONINGTON
1 / 5
Image 1 for STONINGTONImage 2 for STONINGTONImage 3 for STONINGTONImage 4 for STONINGTONImage 5 for STONINGTON
Pet Friendly

STONINGTON

Located on the third floor of the newly renovated historic inn, this front-of-the-inn king bedroom has an ocean view of Eggemoggin Reach and bath with shower.
A/C available....
More Details Calendar
Image 1 for ACADIA Image 2 for ACADIA Image 3 for ACADIA Image 4 for ACADIA Image 5 for ACADIA Image 6 for ACADIA
1 / 6
Image 1 for ACADIAImage 2 for ACADIAImage 3 for ACADIAImage 4 for ACADIAImage 5 for ACADIAImage 6 for ACADIA
Pet Friendly

ACADIA

Located on the third floor of the historic inn, this queen bedroom on the interior hallway has a garden view and private bathroom with tub/shower. A/C available.

118 squa...
More Details Calendar
Image 1 for GREAT SPRUCE HEAD Image 2 for GREAT SPRUCE HEAD Image 3 for GREAT SPRUCE HEAD Image 4 for GREAT SPRUCE HEAD
1 / 4
Image 1 for GREAT SPRUCE HEADImage 2 for GREAT SPRUCE HEADImage 3 for GREAT SPRUCE HEADImage 4 for GREAT SPRUCE HEAD
Pet Friendly

GREAT SPRUCE HEAD

Located on the third floor of the historic inn, this queen bedroom is privately tucked away in the Northwest wing with a garden view and pull-out sofa bed. Bath has tub/showe...
More Details Calendar
Image 1 for EAGLE ISLAND Image 2 for EAGLE ISLAND Image 3 for EAGLE ISLAND
1 / 3
Image 1 for EAGLE ISLANDImage 2 for EAGLE ISLANDImage 3 for EAGLE ISLAND
Pet Friendly

EAGLE ISLAND

Located on the third floor of the historic inn, this back-of-the-inn room with queen bed and large bathroom has option to be rented attached to single second bedroom with twi...
More Details Calendar
Image 1 for EAGLE ISLAND SUITE & BRADBURY Image 2 for EAGLE ISLAND SUITE & BRADBURY Image 3 for EAGLE ISLAND SUITE & BRADBURY Image 4 for EAGLE ISLAND SUITE & BRADBURY Image 5 for EAGLE ISLAND SUITE & BRADBURY Image 6 for EAGLE ISLAND SUITE & BRADBURY
1 / 6
Image 1 for EAGLE ISLAND SUITE & BRADBURYImage 2 for EAGLE ISLAND SUITE & BRADBURYImage 3 for EAGLE ISLAND SUITE & BRADBURYImage 4 for EAGLE ISLAND SUITE & BRADBURYImage 5 for EAGLE ISLAND SUITE & BRADBURYImage 6 for EAGLE ISLAND SUITE & BRADBURY
Pet Friendly

EAGLE ISLAND SUITE & BRADBURY

Located on the third floor of the historic inn, this back-of-the-inn room, Bradbury, is combined with Eagle Island to form one big suite. Eagle Island has one queen bed, Brad...
More Details Calendar
Image 1 for BIRCHES Image 2 for BIRCHES Image 3 for BIRCHES Image 4 for BIRCHES Image 5 for BIRCHES Image 6 for BIRCHES
1 / 6
Image 1 for BIRCHESImage 2 for BIRCHESImage 3 for BIRCHESImage 4 for BIRCHESImage 5 for BIRCHESImage 6 for BIRCHES
Pet Friendly

BIRCHES

DOG FRIENDLY.

We welcome guests and their well-behaved dog for an additional $25/day (per our Pet Policy*).

For stays longer than 5 days, our Weekly Rate for a 7 consec...
More Details Calendar
Image 1 for LEDGES Image 2 for LEDGES Image 3 for LEDGES Image 4 for LEDGES Image 5 for LEDGES Image 6 for LEDGES Image 7 for LEDGES Image 8 for LEDGES
1 / 8
Image 1 for LEDGESImage 2 for LEDGESImage 3 for LEDGESImage 4 for LEDGESImage 5 for LEDGESImage 6 for LEDGESImage 7 for LEDGESImage 8 for LEDGES
Pet Friendly

LEDGES

PERFECT FOR HONEYMOONS! Loaded with rustic Maine charm!

For stays longer than 5 days, our Weekly Rate for a 7 consecutive day stay is generally a better deal. Guest acces...
More Details Calendar
Image 1 for OAK GROVE Image 2 for OAK GROVE Image 3 for OAK GROVE Image 4 for OAK GROVE Image 5 for OAK GROVE Image 6 for OAK GROVE Image 7 for OAK GROVE Image 8 for OAK GROVE
1 / 8
Image 1 for OAK GROVEImage 2 for OAK GROVEImage 3 for OAK GROVEImage 4 for OAK GROVEImage 5 for OAK GROVEImage 6 for OAK GROVEImage 7 for OAK GROVEImage 8 for OAK GROVE
Pet Friendly

OAK GROVE

This beloved cottage sits in its own private grove, perched on a ledge overlooking the ocean.

For stays longer than 5 days, our Weekly Rate for a 7 consecutive day stay i...
More Details Calendar
Image 1 for HOMESTEAD EAST Image 2 for HOMESTEAD EAST Image 3 for HOMESTEAD EAST Image 4 for HOMESTEAD EAST Image 5 for HOMESTEAD EAST Image 6 for HOMESTEAD EAST Image 7 for HOMESTEAD EAST
1 / 7
Image 1 for HOMESTEAD EASTImage 2 for HOMESTEAD EASTImage 3 for HOMESTEAD EASTImage 4 for HOMESTEAD EASTImage 5 for HOMESTEAD EASTImage 6 for HOMESTEAD EASTImage 7 for HOMESTEAD EAST
Pet Friendly

HOMESTEAD EAST

This green cottage sits on the sunrise side of the Homestead duplex on a rocky bluff overlooking the Reach. It has easy drive-up access.

For stays longer than 5 days, ou...
More Details Calendar
Image 1 for HOMESTEAD WEST Image 2 for HOMESTEAD WEST Image 3 for HOMESTEAD WEST Image 4 for HOMESTEAD WEST Image 5 for HOMESTEAD WEST Image 6 for HOMESTEAD WEST
1 / 6
Image 1 for HOMESTEAD WESTImage 2 for HOMESTEAD WESTImage 3 for HOMESTEAD WESTImage 4 for HOMESTEAD WESTImage 5 for HOMESTEAD WESTImage 6 for HOMESTEAD WEST
Pet Friendly

HOMESTEAD WEST

Part of the Homestead duplex, this green cottage sits on the sunset side, on a rocky bluff at the edge of the sea. It has easy drive-up access.

For stays longer than 5 da...
More Details Calendar
Image 1 for FLAGSTAFF Image 2 for FLAGSTAFF Image 3 for FLAGSTAFF Image 4 for FLAGSTAFF Image 5 for FLAGSTAFF Image 6 for FLAGSTAFF Image 7 for FLAGSTAFF Image 8 for FLAGSTAFF Image 9 for FLAGSTAFF Image 10 for FLAGSTAFF
1 / 10
Image 1 for FLAGSTAFFImage 2 for FLAGSTAFFImage 3 for FLAGSTAFFImage 4 for FLAGSTAFFImage 5 for FLAGSTAFFImage 6 for FLAGSTAFFImage 7 for FLAGSTAFFImage 8 for FLAGSTAFFImage 9 for FLAGSTAFFImage 10 for FLAGSTAFF
Pet Friendly

FLAGSTAFF

Perfectly appointed two-bedroom log-style cottage, Flagstaff was built from native trees harvested on site and natural granite from the family quarry. Guest access to two pri...
More Details Calendar
Image 1 for GRINDSTONE Image 2 for GRINDSTONE Image 3 for GRINDSTONE Image 4 for GRINDSTONE Image 5 for GRINDSTONE Image 6 for GRINDSTONE Image 7 for GRINDSTONE Image 8 for GRINDSTONE Image 9 for GRINDSTONE Image 10 for GRINDSTONE
1 / 10
Image 1 for GRINDSTONEImage 2 for GRINDSTONEImage 3 for GRINDSTONEImage 4 for GRINDSTONEImage 5 for GRINDSTONEImage 6 for GRINDSTONEImage 7 for GRINDSTONEImage 8 for GRINDSTONEImage 9 for GRINDSTONEImage 10 for GRINDSTONE
Pet Friendly

GRINDSTONE

DOG FRIENDLY!
We welcome guests and their well-behaved dog for an additional $25/day (per our Pet Policy*).

Grindstone is directly down the way from Flagstaff and has muc...
More Details Calendar
Image 1 for WESTERLY Image 2 for WESTERLY Image 3 for WESTERLY Image 4 for WESTERLY Image 5 for WESTERLY Image 6 for WESTERLY Image 7 for WESTERLY Image 8 for WESTERLY Image 9 for WESTERLY Image 10 for WESTERLY
1 / 10
Image 1 for WESTERLYImage 2 for WESTERLYImage 3 for WESTERLYImage 4 for WESTERLYImage 5 for WESTERLYImage 6 for WESTERLYImage 7 for WESTERLYImage 8 for WESTERLYImage 9 for WESTERLYImage 10 for WESTERLY
Pet Friendly

WESTERLY

This ocean-lovers’ cottage sits right on the Reach, providing access to the most glorious sunrises and sunsets from the living room with its wide swatch of windows, the outdo...
More Details Calendar
Image 1 for ACORN GUEST HOUSE Image 2 for ACORN GUEST HOUSE Image 3 for ACORN GUEST HOUSE Image 4 for ACORN GUEST HOUSE Image 5 for ACORN GUEST HOUSE Image 6 for ACORN GUEST HOUSE Image 7 for ACORN GUEST HOUSE Image 8 for ACORN GUEST HOUSE Image 9 for ACORN GUEST HOUSE
1 / 9
Image 1 for ACORN GUEST HOUSEImage 2 for ACORN GUEST HOUSEImage 3 for ACORN GUEST HOUSEImage 4 for ACORN GUEST HOUSEImage 5 for ACORN GUEST HOUSEImage 6 for ACORN GUEST HOUSEImage 7 for ACORN GUEST HOUSEImage 8 for ACORN GUEST HOUSEImage 9 for ACORN GUEST HOUSE
Pet Friendly

ACORN GUEST HOUSE

In recent years, the Acorn was rented per room, hostel-style, but this practice ceased in 2020, during the pandemic. Still, we kept the names of the separate rooms, all named...
More Details Calendar
|
×
Your Cart is Empty
Add items to your cart to begin your reservation.
Have a gift certificate?
|

Checkout