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

Round Pond Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Round Pond vacation rentals

A bedroom with a bed, a bedside table, and a window with curtains.

1. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (12 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is CA $203
CA $241 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful Intown Studio ~ Walk to Shops & Dining
A wooden deck with a glass door leading to a room.

2. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is CA $112
CA $264 total
includes taxes & fees
Nov 2 - Nov 3
Tiny Cottage Near Everything 10
A cozy living room with a sofa, a small table, and a view of a backyard through large windows.

3. Spacious 1 Bedroom Cottage Close to Everything 2

Spacious 1 Bedroom Cottage Close to Everything 2
Edgecomb
9.4 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay. The cottage had everything that we needed. The cottage was clean and well stocked with the essentials for our visit. Thank you for a nice stay."
United States
Terrence F.
The price is CA $136
CA $291 total
includes taxes & fees
Nov 3 - Nov 4
Spacious 1 Bedroom Cottage Close to Everything 2
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

4. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $117
CA $282 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful Cottage with Loft 9
A small cabin with a wooden deck, surrounded by trees in a wooded area.

5. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is CA $165
CA $325 total
includes taxes & fees
Nov 3 - Nov 4
Spacious 1 Bedroom Cottage Close to Everything 3
Outdoor dining

6. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is CA $203
CA $253 total
includes taxes & fees
Nov 1 - Nov 2
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

7. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
6.4 out of 10, (5 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is CA $245
CA $347 total
includes taxes & fees
Nov 7 - Nov 8
Renovated The Driftwood Cabin at White Anchor Inn
A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

8. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is CA $84
CA $235 total
includes taxes & fees
Nov 2 - Nov 3
Happy Cottage Near Everything 11
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

9. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (19 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
The price is CA $109
CA $271 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful Cottage Close to Everything 12
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

10. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is CA $115
CA $282 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 1 Bedroom Cottage Close to Everything 5
A kitchen with wooden ceiling, a bar area with two chairs, a red appliance, and a view of the outdoors.

11. Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (26 reviews)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Canada
Christine M.
The price is CA $145
CA $302 total
includes taxes & fees
Nov 3 - Nov 4
Spacious 1 Bedroom Close to Everything 4
A cozy bedroom with a wooden ceiling, a large bed with a blue blanket, a desk with a chair, and a window with curtains.

12. Cheerful Cottage with Loft Close to Everything 6

Cheerful Cottage with Loft Close to Everything 6
Edgecomb
9.4 out of 10, Exceptional, (11 reviews)
"Very clean and comfortable little cottage. Host responds and communicates effectively. Very nice experience."
United States
Yaoyubai
The price is CA $123
CA $291 total
includes taxes & fees
Nov 9 - Nov 10
Cheerful Cottage with Loft Close to Everything 6
A spacious living room with a beige sectional sofa, a round coffee table, and a teal armchair. Large windows with white curtains allow natural light to fill the room.

13. Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920

Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is CA $426
CA $918 total
includes taxes & fees
Nov 15 - Nov 16
Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
A wooden staircase with a wooden railing, surrounded by green foliage.

14. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is CA $173
CA $252 total
includes taxes & fees
Nov 1 - Nov 2
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

15. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (72 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is CA $200
CA $402 total
includes taxes & fees
Nov 1 - Nov 2
A Spacious Vacation Cottage in Sheepscot Harbour
A treehouse with a wooden staircase and a small building with a colorful mural.

16. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
Bath
8.0 out of 10, Very good, (31 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 CA $169
CA $248 total
includes taxes & fees
Nov 1 - Nov 2
Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
A modern kitchen with a central island, bar stools, and a dining area with a view of trees.

17. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (64 reviews)
"Tucked away in a wooded lot, quick drive to Boothbay Harbor. Side by side units are great for friends or families traveling together."
United States
Carly C.
The price is CA $338
CA $731 total
includes taxes & fees
Nov 1 - Nov 2
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
Two Adirondack chairs facing a body of water with a bridge in the background.

18. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Edgecomb
9.8 out of 10, Exceptional, (90 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is CA $252
CA $463 total
includes taxes & fees
Nov 1 - Nov 2
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
A lakeside deck with a fire pit, docked boats, and a wooden railing.

19. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (129 reviews)
"This place was the definition of relaxation! The access to West Harbor "Pond" (it's huge -- more like a lake!) was unbeatable! We were able to use the provided kayaks to explore the little islands in the water and to come really close to a pair of loons!"
United States
Melinda M.
The price is CA $252
CA $445 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
A cabin with a wooden exterior, a glass door, and a sign indicating it is a camp.

20. Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
9.8 out of 10, Exceptional, (8 reviews)
"Very nice and very quiet "
United States
justin s.
The price is CA $161
CA $439 total
includes taxes & fees
Nov 9 - Nov 10
Tiny A-Frame Romantic Getaway
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

Five Gables Inn

Five Gables Inn

10/10 Excellent
"From the moment I walked in until the time we left, everything was perfect. I love the property, the staff and the views. If I ever find myself in that area again, I will definitely stay there."
Frank J 1-night trip
Posted 8 hours ago
Five Gables Inn

Find out more about Round Pond

Everything you need to know about Round Pond vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Round Pond vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Round Pond vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Round Pond vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Round Pond. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Round Pond vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Round Pond vacation rentals we have selected for you start as low as CA $177 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Round Pond rentals

At Expedia, we put the best Round Pond vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Round Pond rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Round Pond vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Round Pond. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Round Pond?

Yes, we offer vacation rentals near top points of interest in Round Pond, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Round Pond has to offer?

Perfect stopover, getaway, base to explore the area, or to simply stay in town. : This vacation home rental outside of Round Pond offers a selection of books and WiFi to help you feel comfortable in your new surroundings. Kitchen amenities include an electric kettle to make your meal-planning easier.

How many vacation rentals are there in Round Pond?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Round Pond stay.

What’s there to see and do in Round Pond?

While exploring the area, visit family-friendly sights like Boothbay Railway Village, or get outside and enjoy nature at La Verna Preserve. Pemaquid Beach Park and Pemaquid Point Lighthouse Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Round Pond like?

Vacation rentals are private properties where you can stay for a couple of days or more in Round Pond. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.