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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Cottages in Round Pond

Pauls Cottage in Tenants Harbor, 1 Min to Shore
Relax on the covered porch with Adirondack chairs and a small table, perfect for outdoor dining or unwinding.

Pauls Cottage in Tenants Harbor, 1 Min to Shore

3.0 star property
Pauls Cottage in Tenants Harbor, 1 Min to Shore
Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!
Enjoy meals in this cozy dining area with a glass-top table and comfortable seating for four.

Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!

3.0 star property
Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!
Ocean Inlet Cottage w/ Deck & Grill!
House (2 Bedrooms) | Interior

Ocean Inlet Cottage w/ Deck & Grill!

3.0 star property
Ocean Inlet Cottage w/ Deck & Grill!
Deck w/ Water Views: Quiet East Boothbay Retreat!
Relax on the covered deck with a rocking chair, taking in the views of the surrounding neighborhood.

Deck w/ Water Views: Quiet East Boothbay Retreat!

3.0 star property
Deck w/ Water Views: Quiet East Boothbay Retreat!
'sprucewold' Boothbay Harbor Cottage w/ Deck
Cottage (2 Bedrooms) | Interior

'sprucewold' Boothbay Harbor Cottage w/ Deck

3.0 star property
'sprucewold' Boothbay Harbor Cottage w/ Deck
3 Mi to Boothbay Harbor: Coastal Colorful Home!
House (2 Bedrooms) | Interior

3 Mi to Boothbay Harbor: Coastal Colorful Home!

3.0 star property
3 Mi to Boothbay Harbor: Coastal Colorful Home!
Charming East Boothbay Cottage w/ Large Yard!
Cozy living area with a sofa, armchairs, coffee table, and fireplace.

Charming East Boothbay Cottage w/ Large Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Really nice place to stay to visit Boothbay Region"
Charming East Boothbay Cottage w/ Large Yard!
On-site Pond: Spacious Family Home in Jefferson!
Charming two-story house with a classic porch and serene surroundings.

On-site Pond: Spacious Family Home in Jefferson!

3.0 star property
On-site Pond: Spacious Family Home in Jefferson!
Charming Owls Head Retreat: 2 Mi to Rockland Coast
Relax in the living room with a sofa and chair, a dining table, and a kitchen view.

Charming Owls Head Retreat: 2 Mi to Rockland Coast

3.0 star property
Charming Owls Head Retreat: 2 Mi to Rockland Coast
Updated Tiny House: Walk to Wiscasset Village
Situated in a wooded area, this cabin features a steeply pitched roof and a white front door.

Updated Tiny House: Walk to Wiscasset Village

3.0 star property
Updated Tiny House: Walk to Wiscasset Village
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
House (3 Bedrooms) | Interior

Boothbay Harbor Cabin w/ Spacious Deck & Yard!

3.0 star property
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
Historic Waldoboro House Near Lakes, Boating, Etc!
House (3 Bedrooms) | Interior

Historic Waldoboro House Near Lakes, Boating, Etc!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
Historic Waldoboro House Near Lakes, Boating, Etc!
Walk to Barrett's Park: Wooded Cabin w/ Grill!
Interior

Walk to Barrett's Park: Wooded Cabin w/ Grill!

3.0 star property
Walk to Barrett's Park: Wooded Cabin w/ Grill!
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Relax in a serene room with a view of the water and forest, featuring a seating area and large windows.

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Historic Friendship Boat House Near Back River!
House (3 Bedrooms) | Interior

Historic Friendship Boat House Near Back River!

3.0 star property
Historic Friendship Boat House Near Back River!
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
Cottage (2 Bedrooms) | Interior

Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

3.0 star property
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
Cozy Waterfront Cottage on Montsweag Bay!
Cottage (3 Bedrooms) | Interior

Cozy Waterfront Cottage on Montsweag Bay!

3.0 star property
Cozy Waterfront Cottage on Montsweag Bay!
Historic Bath Home, Walk to Waterfront Park!
House (4 Bedrooms) | Front of property

Historic Bath Home, Walk to Waterfront Park!

3.0 star property
Historic Bath Home, Walk to Waterfront Park!
Georgetown Vacation Rental: Gas Grill & Near Beach
Kitchen features a central island, white cabinets, stainless steel sink, and a dishwasher.

Georgetown Vacation Rental: Gas Grill & Near Beach

3.0 star property
Georgetown Vacation Rental: Gas Grill & Near Beach
Spacious Round Pond House w/ On-site Trail Access!
Enjoy meals in this traditional dining area with a long table, comfortable chairs, and decorative touches.

Spacious Round Pond House w/ On-site Trail Access!

3.0 star property
Spacious Round Pond House w/ On-site Trail Access!
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.
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Top Round Pond Hotel Reviews

Flagship Inn and Suites

Flagship Inn and Suites

10/10 Excellent
"We had a great stay, would definitely stay here when visiting again "
Alexis 1-night trip
Posted 2 days ago
Flagship Inn and Suites

Frequently asked questions

How much do cottages in Round Pond cost?
Cottages in Round Pond range between and per night. These properties offer a chance to soak in nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Round Pond?
Stay close to nature in one of the 33 cottages available in Round Pond. To help you find an ideal place, use our filter tool to search for must-have perks or amenities.
Why book your cottage in Round Pond with Expedia?
Reserving a cottage in Round Pond is as simple as entering your travel dates and selecting your ideal place for outdoor recreation and relaxation. From chic retreats to budget-friendly stays and cottages that have amenities like laundry facilities, Expedia has something for all tastes. As for terrific deals? We have them too!