Round Pond Vacation Rentals from $158: Search Short-Term Rentals

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Our top choices for Round Pond vacation rentals

A patio with a round glass table and two chairs, overlooking a grassy area with trees.

1. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Boothbay

Cassie M.

$150 nightly

Sep 7 - Sep 8

Total with taxes and fees

A fenced garden area with a wooden gate, surrounded by greenery and trees.

2. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Boothbay

Audreyana P.

$189 nightly

Sep 7 - Sep 8

Total with taxes and fees

A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

3. Cheerful Cottage with Loft 9

Edgecomb

Daniel B.

$231 nightly

Sep 7 - Sep 8

Total with taxes and fees

A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

4. Spacious 1 Bedroom Cottage Close to Everything 5

Edgecomb

Theresa

$247 nightly

Sep 14 - Sep 15

Total with taxes and fees

A wooden deck with a glass door leading to a room.

5. Tiny Cottage Near Everything 10

Edgecomb

Elaine

$215 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

6. Peaceful Intown Studio ~ Walk to Shops & Dining

Newcastle

Caycee A.

$195 nightly

Sep 13 - Sep 14

Total with taxes and fees

A small cabin with a wooden deck, surrounded by trees in a wooded area.

7. Spacious 1 Bedroom Cottage Close to Everything 3

Edgecomb

Bruce O.

$272 nightly

Sep 8 - Sep 9

Total with taxes and fees

Two Adirondack chairs facing a body of water with a bridge in the background.

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

Edgecomb

Ann M.

$277 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a window providing natural light.

9. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

East Boothbay

Judith

$505 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern kitchen with dark cabinets, a central island with bar stools, and a dining area with a round table and chairs.

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

East Boothbay

Elaine G.

$505 nightly

Sep 7 - Sep 8

Total with taxes and fees

A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

11. A Spacious Vacation Cottage in Sheepscot Harbour

Edgecomb

Julie D.

$294 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Waldoboro

$189 nightly

Sep 15 - Sep 16

Total with taxes and fees

13. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Boothbay

Joseph B.

$212 nightly

Sep 13 - Sep 14

Total with taxes and fees

A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

14. Cheerful Cottage Close to Everything 12

Edgecomb

Lynn R.

$232 nightly

Sep 7 - Sep 8

Total with taxes and fees

A wooden deck with two blue Adirondack chairs, surrounded by white flowers and trees.

15. Luxury Yurt at Seaside Farm in Friendship

Friendship

$598 nightly

Sep 27 - Sep 28

Total with taxes and fees

A kitchen with wooden ceiling, a bar area with two chairs, a red appliance, and a view of the outdoors.

16. Spacious 1 Bedroom Close to Everything 4

Edgecomb

Christine M.

$257 nightly

Sep 7 - Sep 8

Total with taxes and fees

A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

17. Happy Cottage Near Everything 11

Edgecomb

George

$195 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a round rug.

18. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Waldoboro

Deborah

$450 nightly

Sep 9 - Sep 10

Total with taxes and fees

A wooden deck with a view of a lake and trees.

19. 1920s Riverfront Cottage – Historic Maine Charm

Edgecomb

Sam D.

$410 nightly

Sep 7 - Sep 8

Total with taxes and fees

20. Renovated The Driftwood Cabin at White Anchor Inn

Boothbay

"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."

Abra H.

$240 nightly

Sep 13 - Sep 14

Total with taxes and fees

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Top Round Pond Hotel Reviews

Fishermans Wharf Inn

10/10 Excellent

"We paid for a room that overlooked the harbor, and the view was amazing. We ate at the tavern one night and the service and food was good. The hotel is in a super convenient spot to walk to all the shops and restaurants."

Bluebird Ocean Point Inn

8/10 Good

"I like that what appears a vintage property has been modernized with tasteful room decor and nice beds/bathrooms. Our two queen bed room was cozy and but a touch small if you travel with a large assortment of travel items! The view of the water was very nice. The Adirondack chairs were in a perfect locale to sit outdoors! I watched the seabirds and the lobster boats working away right in front of our property. It was quiet overnight. It’s great for couples or family. The dining room served a nice but a lil pricey breakfast."

Topside Inn

10/10 Excellent

"This was by far our best Boothbay experience in over 28 years of vacationing there. Admittedly, this was a splurge we had to save up for, but it was worth every penny. Greg (the general manager) was exceptional in his efforts to welcome every guest and make sure they had what they need to have a wonderful stay. Housekeeping staff were ready to respond with smiles and "hellos." The evening bartender was top notch for her pours and for keeping on top of guests' needs. The morning breakfast crew were beyond compare in their agility in staying on top of clearing dishes and refreshing buffet components. ...And the CHEF! Gourmet breakfasts that are picture-worthy and 5-star in quality and taste. The property itself provides amazing views and comfortable furniture throughout, and it's worth mentioning the hospitality room that provides coffee, tea, sodas and light snacks 24-7. This all sounds too good to be true...but it is. We are already strategizing when/how to get back there. The only "catch" worth mentioning is because this wonderful inn is located on a hill overlooking the harbor, there is (obviously) a hill to drive or walk up to get to it. It is literally a five-minute walk to the downtown harbor area, which is perfect for shopping, sea excursions, and dining options. Getting back up takes a little bit of effort, but it is doable. My husband and I are obese and managed the walk up and down several times daily and have no qualms about returning to do that again"

Linekin Bay Resort

10/10 Excellent

"Breakfast was the best we have found, so far for complimentary breakfast in the Boothbay Area. While all are pretty much the same ingredients, this buffet was well managed and attended so everything was fresh and hot. The banana walnut pancakes were a nice change and french toast was fresh along with the standard waffle making station."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Round Pond in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

Slow Down & Go Back in Time-Relax Completely in Our Maine Home: This vacation home rental outside of Round Pond is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

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.

Round Pond Vacation Rentals

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Check prices for these dates

Our top choices for Round Pond vacation rentals

1. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

2. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

3. Cheerful Cottage with Loft 9

4. Spacious 1 Bedroom Cottage Close to Everything 5

5. Tiny Cottage Near Everything 10

6. Peaceful Intown Studio ~ Walk to Shops & Dining

7. Spacious 1 Bedroom Cottage Close to Everything 3

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

9. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

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

11. A Spacious Vacation Cottage in Sheepscot Harbour

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

13. Newly Renovated Cozy Cove Cabin at White Anchor Inn

14. Cheerful Cottage Close to Everything 12

15. Luxury Yurt at Seaside Farm in Friendship

16. Spacious 1 Bedroom Close to Everything 4

17. Happy Cottage Near Everything 11

18. Near Lakes, Bay & Trails! Historic Waldoboro Gem

19. 1920s Riverfront Cottage – Historic Maine Charm

20. Renovated The Driftwood Cabin at White Anchor Inn

Find vacation rentals that suit your style

Top Round Pond Hotel Reviews

Fishermans Wharf Inn

Find out more about Round Pond

Explore a world of travel with Expedia

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