A calm harbor at sunset with boats docked, a wooden pier, and a clear sky.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Round Pond vacation homes

Beach

1. Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (5 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
The price is AED 1,194
AED 2,631 total
includes taxes & fees
20 Sep - 21 Sep
Pemaquid Escape | Curated Comfort + Hot Tub
Terrace/patio

2. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is AED 1,333
AED 2,893 total
includes taxes & fees
3 Oct - 4 Oct
Luxury Yurt at Seaside Farm in Friendship
Outdoor dining

3. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.2 out of 10, Very good, (29 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AED 410
AED 651 total
includes taxes & fees
23 Sep - 24 Sep
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Property grounds

4. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful spot. Make sure to use the hot tub!"
United States
Sam D.
The price is AED 775
AED 1,534 total
includes taxes & fees
28 Sep - 29 Sep
1920s Riverfront Cottage – Historic Maine Charm
Interior

5. 3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (13 reviews)
"Great property with central location in mid coast Maine. Beautifully decorated with very comfortable beds! Jeff was great with communication throughout to ensure we had everything we needed! Would stay again! "
United States
Decourcey D.
The price is AED 1,058
AED 1,845 total
includes taxes & fees
21 Sep - 22 Sep
3 Bedroom Happy Cottage 15
Property grounds

6. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (30 reviews)
"Location, location, location! We stayed for 4 days and didn't have to drive ONCE. David was easy to communicate with and very helpful. House was clean and comfortable. Would definitely stay again!"
United States
Justin T.
The price is AED 613
AED 1,257 total
includes taxes & fees
19 Oct - 20 Oct
Boothbay Harbor, 2-Story Cottage, downtown
House, 1 Queen Bed (Beehive Cottage) | Living area

7. Bee Hive Cottage, Romantic Maine Waterfront Cottag

Bee Hive Cottage, Romantic Maine Waterfront Cottag
2.0 star property
Cushing
Bee Hive Cottage, Romantic Maine Waterfront Cottag
Property grounds

8. Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!

Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!
Bath
8.2 out of 10, Very good, (20 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AED 454
AED 699 total
includes taxes & fees
28 Sep - 29 Sep
Captain's House. The fall in Maine! Enjoy the colors, weather & quality air!
Property grounds

9. Joyful Maine Escape: A Three-Bedroom Water View Townhouse

Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Edgecomb
10.0 out of 10, Exceptional, (54 reviews)
"Great location for a trip up the Maine coast. "
United States
Steve M.
The price is AED 988
AED 1,702 total
includes taxes & fees
20 Sep - 21 Sep
Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Smart TV, fireplace

10. Bee Hive Cottage, romantic Maine waterfront cottag

Bee Hive Cottage, romantic Maine waterfront cottag
Cushing
10.0 out of 10, Exceptional, (1 review)
"we enjoyed sipping coffee in the morning watching the lobster boats go to/from the working harbor next door."
United States
Karen L.
Bee Hive Cottage, romantic Maine waterfront cottag
Smart TV

11. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is AED 547
AED 1,117 total
includes taxes & fees
20 Oct - 21 Oct
Peaceful, Centrally Located Home with Seasonal River Views
Interior

12. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (49 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Smart TV

13. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (54 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is AED 551
AED 1,117 total
includes taxes & fees
22 Sep - 23 Sep
2 Bedroom Close to Town Home
Property grounds

14. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (13 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is AED 511
AED 981 total
includes taxes & fees
12 Oct - 13 Oct
Bright 2-Bedroom Apartment Near Downtown Thomaston
Desk, iron/ironing board, WiFi (free), bed sheets

15. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is AED 801
AED 1,498 total
includes taxes & fees
18 Oct - 19 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
1 bedroom, WiFi (free), bed sheets

16. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (33 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is AED 397
AED 601 total
includes taxes & fees
8 Oct - 9 Oct
Simplicity-Just what you need! STR24-20
Terrace/patio

17. 2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.

2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (25 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is AED 768
AED 953 total
includes taxes & fees
21 Sep - 22 Sep
2BR Apt. Authenticity, value, walk to everything. big yard, treehouse. No fees.
Coffee/tea maker, fridge, microwave, oven

18. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (51 reviews)
"Host communication was excellent. Location was ideal, walkable to the Boothbay Harbor attractions. Nice new wooden floors upstairs with the bedrooms. No AC which was fine for our stay. We must have stayed the first of the season, as the negatives were related to this. The toilets were disgusting with a foul odor and green mold on toilet seats, presumably from 9 months of zero use and the maids not cleaning prior to our arrival. Either way they should be replaced. All else with home was fine."
United States
Timothy M.
The price is AED 1,396
AED 2,650 total
includes taxes & fees
20 Sep - 21 Sep
Boothbay Harbor, The Francis Greene House, downtown
Terrace/patio

19. Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
10.0 out of 10, Exceptional, (1 review)
"Perfect for peace"
United States
John S.
Tide Haven Cottage on Bay Point
Coffee/tea maker, fridge, microwave, oven

20. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place at a great price!"
United States
Stephen H.
The price is AED 845
AED 1,661 total
includes taxes & fees
16 Oct - 17 Oct
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
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

Topside Inn

Topside Inn

10/10 Excellent
"Perfect stay. Clean. Beautiful view"
Wilder 1-night trip
Posted 9 hours ago
Topside Inn