Book Holiday Homes in Round Pond

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 Round Pond

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.

Owls Head
The price is AU$629 per night from 1 Sept to 2 Sept
AU$629
1 Sept - 2 Sept
includes taxes & fees
When you stay at this vacation home in Owls Head, you'll be by the sea, within a 5-minute drive of Breakwater Vineyards and Coastal Children's Museum.
Comfortable, Close to Town Home, with Oceanview.
Captain's Quarters  Guest Room w/Private Bath & Entrance. Best Value in Town!

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Bath
The price is AU$254 per night from 13 Aug to 14 Aug
AU$254
13 Aug - 14 Aug
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
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$531 per night from 26 Aug to 27 Aug
AU$531
26 Aug - 27 Aug
includes taxes & fees
With a stay at this vacation home in Nobleboro, you'll be within a 15-minute drive of Damariscotta Lake and Damariscotta Lake State Park.
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Beachfront Delight with detached guesthouse, sunset views & private beach access

Beachfront Delight with detached guesthouse, sunset views & private beach access

Southport
Located in Southport, this vacation home is by the ocean, within a 15-minute walk of Hendricks Head Beach and Hendricks Head Light.
Beachfront Delight with detached guesthouse, sunset views & private beach access
Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town

Wiscasset
Located in Wiscasset, this vacation home is by the sea, within a 10-minute drive of Lincoln County Jail Museum and Wiscasset Historic District.
Peaceful home with forest views & great yard - minutes to town
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

Boothbay Harbor
The price is AU$740 per night from 24 Aug to 25 Aug
AU$740
24 Aug - 25 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Boothbay Harbor, steps from Burnt Island Living Lighthouse and 4 minutes by foot from Boothbay Harbor ...
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

Bristol
When you stay at this vacation home in New Harbor, you'll be by the sea, within a 5-minute drive of Pemaquid Point Lighthouse Park and Pemaquid Craft Co-op.
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2 out of 5
South Thomaston
Located in South Thomaston, this vacation home is by the ocean, within a 10-minute drive of General Henry Knox Museum and Maine State Prison Store.
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm
Don't see what you're looking for?
See all available properties in Round Pond
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.

Round Pond 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 Round Pond vacation homes are the perfect way for you to wing it.

Holiday houses in Round Pond 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 Round Pond 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 Round Pond adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Round Pond 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 Round Pond 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.

Round Pond Holiday Homes essential information

Accommodation
526 Holiday Homes
Lowest Price
AU$250
Highest Price
AU$740
Popular accommodation
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Comfortable, Close to Town Home, with Oceanview., Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!, “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage, Beachfront Delight with detached guesthouse, sunset views & private beach access, Peaceful home with forest views & great yard - minutes to town, Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn, Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views, Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Top trending hotels in Round Pond

Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 1 Sept to 2 Sept
AU$270
1 Sept - 2 Sept
includes taxes & fees
Located in Southport, Ocean Gate Resort is by the ocean, a 4-minute drive from Hendricks Hill Museum and 5 minutes from Juniper Point.
Ocean Gate Resort
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
The price is AU$250 per night from 4 Sept to 5 Sept
AU$250
4 Sept - 5 Sept
includes taxes & fees
With a stay at Flagship Inn and Suites in Boothbay Harbor, you'll be a 1-minute walk from Carousel Music Theater and 6 minutes by foot from Boothbay Region Land ...
Flagship Inn and Suites
Fishermans Wharf Inn

Fishermans Wharf Inn

2.5 out of 5
22 Commercial St, Boothbay Harbor, ME
The price is AU$385 per night from 7 Sept to 8 Sept
AU$385
7 Sept - 8 Sept
includes taxes & fees
With a stay at Fishermans Wharf Inn, you'll be centrally located in Boothbay Harbor, steps from Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Fishermans Wharf Inn
Save an average of 15% on thousands of hotels when you're signed in
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
191 Shore Road, East Boothbay, ME
The price is AU$281 per night from 2 Sept to 3 Sept
AU$281
2 Sept - 3 Sept
includes taxes & fees
With a stay at Bluebird Ocean Point Inn in East Boothbay (Ocean Point), you'll be steps from Linekin Bay and a 3-minute drive from Grimes Cove Beach.
Bluebird Ocean Point Inn
Don't see what you're looking for?
See all available properties in Round Pond
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.