Book Holiday Homes in Rockland

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Rockland

Gorgeous new mid-coast listing! Large, family friendly home, perfect location!

Gorgeous new mid-coast listing! Large, family friendly home, perfect location!

Rockport
Located in Rockport, this vacation home is within a 5-minute drive of Chickawaukee Lake and Chickawaukie Pond.
Gorgeous new mid-coast listing! Large, family friendly home, perfect location!
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

Saint George
Located in Tenants Harbor, this vacation home is within a 15-minute drive of Tenants Harbor Marina and Marshall Point Lighthouse.
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

Lincolnville
With a stay at this vacation home in Lincolnville, you'll be a 1-minute walk from Windsor Chairmakers and 8 minutes by foot from Lincolnville Beach.
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!
Save an average of 15% on thousands of hotels when you're signed in
“Otter Getaway”
Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro
The price is AU$700 per night from 23 Dec to 24 Dec
AU$700
includes taxes & fees
23 Dec - 24 Dec
When you stay at this vacation home in Nobleboro, you'll be steps from Damariscotta Lake.
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Waterfront home with beautiful bay views - near shops & dining

Waterfront home with beautiful bay views - near shops & dining

Owls Head
Located in Owls Head, this vacation home is by the ocean, within a 15-minute walk of Sail Power and Steam Museum and Snow Marine Park.
Waterfront home with beautiful bay views - near shops & dining
The RiverView

The RiverView

Thomaston
The price is AU$494 per night from 26 Dec to 27 Dec
AU$494
includes taxes & fees
26 Dec - 27 Dec
Located in Thomaston, this vacation home is within a 5-minute drive of General Henry Knox Museum and Maine State Prison Store.
The RiverView
Breathtaking views, total relaxation, do as much or as little as you choose

Breathtaking views, total relaxation, do as much or as little as you choose

Owls Head
Located in Owls Head, this vacation home is by the ocean, within a 10-minute drive of Lucia Beach and Breakwater Vineyards.
Breathtaking views, total relaxation, do as much or as little as you choose
Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters

Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters

Newcastle
When you stay at this vacation home in Newcastle, you'll be on a river, within a 5-minute drive of Frances Perkins Center and Jan Kilburn Watercolor Studio and ...
Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Searsmont
When you stay at this vacation home in Searsmont, you'll be in the mountains and 7 minutes by car from St. George River.
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Don't see what you're looking for?
See all available properties in Rockland
View all properties
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.

Rockland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Rockland vacation homes are the perfect way for you to wing it.

Holiday houses in Rockland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Rockland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Rockland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Rockland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Rockland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Rockland Holiday Homes essential information

Accommodation
250 Holiday Homes
Lowest Price
AU$199
Highest Price
AU$700
Popular accommodation
Gorgeous new mid-coast listing! Large, family friendly home, perfect location!, The Perch - A cozy cottage minutes from Tenants Harbor, with water access!, Stay in this beautiful home: ocean views and access to midcoast Maine's charm! , “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage, Waterfront home with beautiful bay views - near shops & dining, The RiverView, Breathtaking views, total relaxation, do as much or as little as you choose, Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters , Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Top trending hotels in Rockland

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 5 Jan to 6 Jan
AU$199
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Trade Winds on the Bay places you in the heart of Rockland, steps from Maine Lighthouse Museum and Project Puffin Visitor Center.
Trade Winds on the Bay
Rockland Harbor Hotel

Rockland Harbor Hotel

2.5 out of 5
520 Main Street, Rockland, ME
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 16 Jan to 17 Jan
AU$265
includes taxes & fees
16 Jan - 17 Jan 2025
A stay at Rockland Harbor Hotel places you in the heart of Rockland, steps from Rockland Ferry Terminal and 3 minutes by foot from Strand Theater.
Rockland Harbor Hotel
Hatchway Hotel

Hatchway Hotel

3 out of 5
6 Park Drive, Rockland, ME
A stay at Hatchway Hotel places you in the heart of Rockland, steps from Maine Lighthouse Museum and Buoy Park.
Hatchway Hotel
Save an average of 15% on thousands of hotels when you're signed in
250 Main Hotel

250 Main Hotel

3 out of 5
250 Main Street, Rockland, ME
The price is AU$330 per night from 1 Jan to 2 Jan
AU$330
includes taxes & fees
1 Jan - 2 Jan 2025
When you stay at 250 Main Hotel in Rockland, you'll be near the airport, just steps from Maine Coastal Islands National Wildlife Refuge Visitor Center and 2 ...
250 Main Hotel
Don't see what you're looking for?
See all available properties in Rockland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.