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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Cottages in Round Pond

Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Terrace/patio

Charming 3-bedroom cottage in Southport with water views and close to Boothbay.

Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (53)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

Enjoyable 1-bedroom rustic cottage in Southport.
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Exterior

Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

10.0 out of 10, Exceptional, (64)
"The cottage was perfect for a post Christmas relaxing week of downtime."
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Premier Cottage w/NEW ADDITION! Great for large families/multiple couples
Beach

Premier Cottage w/NEW ADDITION! Great for large families/multiple couples

10.0 out of 10, Exceptional, (39)
"We had a great stay. The cabin is exactly as described. All the amentities one would need. Beautiful area."
Premier Cottage w/NEW ADDITION! Great for large families/multiple couples
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Property grounds

Waterfront Cottage in South Bristol w/ private dock and lobster boat views

10.0 out of 10, Exceptional, (99)
"We stayed at the property for two nights for a family getaway after the holidays. The house was in a great location, beautiful views, spotlessly clean, and very well equipped. We loved waking up to the light hitting the water and being able to explore the beautiful peninsula. Great hikes a short drive away. We would gladly stay again! "
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
TV, fireplace, DVD player, books

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.0 out of 10, Wonderful, (64)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Interior

Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town

9.6 out of 10, Exceptional, (25)
"Convenient and cozy. Lovely wooded lot with views. "
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Outdoor dining

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (41)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Terrace/patio

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (66)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
TV

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.6 out of 10, Exceptional, (46)
"Absolutely beautiful views. Very well appointed and comfortable. "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Beach

Cozy Cottage with spectacular salt water view / 3 Kayaks available/

9.8 out of 10, Exceptional, (39)
"The property is exactly like the pictures but better. The view is amazing, location is quite and comfortable. Easy access the many towns & hiking locations. Would stay again."
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay
Beach nearby

Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay

5.6 out of 10, (5)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay
Newly updated cottage directly on Maple Juice Cove
Aerial view

Newly updated cottage directly on Maple Juice Cove

10.0 out of 10, Exceptional, (33)
"Great place and great host!"
Newly updated cottage directly on Maple Juice Cove
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

8.4 out of 10, Very Good, (6)
"Great location, easy to get to lots of coastal regions. Property is clean and cozy."
Updated Tiny House: Walk to Wiscasset Village
'Sprucewold' Boothbay Harbor Cottage w/ Deck
Exterior

'Sprucewold' Boothbay Harbor Cottage w/ Deck

9.8 out of 10, Exceptional, (13)
"Clean, great screened in porch, comfortable beds, nice kitchen and comfortable furniture in main room. The flower boxes were beautiful"
'Sprucewold' Boothbay Harbor Cottage w/ Deck
"The Cottage " is Perfect couples retreat!
Property grounds

"The Cottage " is Perfect couples retreat!

9.6 out of 10, Exceptional, (26)
"Lovely, quiet retreat. Would definitely stay again."
"The Cottage " is Perfect couples retreat!
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (50)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Olde Post Office Cottage at Pemaquid Point
Fitness facility

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (138)
"This is our second time staying here, and as before, it was delightful. Obvious that the owner puts a lot of care and thought into the place."
Olde Post Office Cottage at Pemaquid Point
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
Exterior detail

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (80)
"My husband and I just retired and enjoyed this place immensely! Especially the fireplace and the quiet space."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
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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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 247 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!