Round Pond holiday rentals

We found 891 holiday rentals — enter your dates for availability
Select from 11 homes, 10 cottages and other holiday rentals in Round Pond to find one that's perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a hot tub. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Round Pond

Showing deals for:8 Jan - 15 Jan

Interior
Property grounds
Dining
Living area
Exceptional
(89 reviews)

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Edgecomb

8% off
AU$2,876
for 7 nights, 1 cottage
AU$411 per night
includes taxes & fees
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Private kitchen
Property grounds
Exterior
Interior
Exceptional
(54 reviews)

Joyful Maine Escape: A Three-Bedroom Water View Townhouse

Edgecomb

8% off
AU$3,522
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Property grounds
Living area
Interior
Exterior
Exceptional
(70 reviews)

A Spacious Vacation Cottage in Sheepscot Harbour

Edgecomb

8% off
AU$2,408
for 7 nights, 1 cottage
AU$344 per night
includes taxes & fees
A Spacious Vacation Cottage in Sheepscot Harbour
First Floor Queen Bedroom with an attached second bathroom.
Sea view through wavy glass in living room.
Pick your chair. While watching the Friendship Lobster Boast Races.
Your " Private" wharf from water.
Exceptional
(100 reviews)

Historic "Wilbur Morse" Friendship Maine Ocean Home

Friendship

7% off
AU$9,423
for 7 nights, 1 home
AU$1,346 per night
includes taxes & fees
Historic "Wilbur Morse" Friendship Maine Ocean Home
Upstairs balcony entry third bedroom
Mossy Glen Lodge - entire lodge is your private secluded hideaway
Christmas look at Mossy Glenn Lodge
Stairs from second and third bedroom
Exceptional
(23 reviews)

Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock

Boothbay

13% off
AU$3,224
for 7 nights, 1 room
AU$461 per night
includes taxes & fees
Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock
Galley Kitchen with dining counter.
Living Room (Full Sleep Sofa), Open Kitchen, Adjacent Dining Room
Fall Colors at Sea Lavender
Fire pit (wood provided) along the shore
Exceptional
(74 reviews)

Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

Newcastle

6% off
AU$2,851
for 7 nights, 1 cottage
AU$407 per night
includes taxes & fees
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Exterior
Outdoor dining
Upstairs master bedroom view
Kitchen
Exceptional
(38 reviews)

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor

8% off
AU$3,912
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Screen porch
Exterior
Living area
Living area
Exceptional
(9 reviews)

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

East Boothbay

8% off
AU$4,091
for 7 nights, 1 home
AU$584 per night
includes taxes & fees
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Portside's deck
Living room
Back Bay Cottage, next to the Chowder House in downtown Boothbay Harbor
Kitchen
Exceptional
(77 reviews)

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

Boothbay Harbor

12% off
AU$3,372
for 7 nights, 1 apartment
AU$482 per night
includes taxes & fees
Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor
Outdoor dining
Aerial view of condo on the left side.
Kitchen with granite counter top and high top seating.
Living room.
Exceptional
(9 reviews)

Beautiful Condo on Ocean Cove - Easy walk to harbor-side town

Boothbay Harbor

8% off
AU$4,545
for 7 nights, 1 apartment
AU$649 per night
includes taxes & fees
Beautiful Condo on Ocean Cove - Easy walk to harbor-side town
Relax with friends around the fireplace in the Livingroom.
Sea-air nourishes our flowerbox blossoms all summer--
Charming on your arrival...
The large lawns allow for many outdoor gatherings too!
Exceptional
(97 reviews)

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

New Harbor

7% off
AU$2,046
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Slow Down & Go Back in Time-Relax Completely in Our Maine Home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The natural setting of Round Pond is ready to explore

Learn about the unique charm of Round Pond with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Round Pond

Do you want to discover top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Round Pond a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Maine State Aquarium (10.5 mi / 16.9 km)
  • Maine State Prison Store (17.1 mi / 27.5 km)
  • Pemaquid Craft Co-op (3.9 mi / 6.3 km)
  • Boothbay Golf Course (8.9 mi / 14.4 km)

Exploring the natural landscape of Round Pond

Whether you're an outdoor enthusiast or just want to take in the scenery, Round Pond is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • La Verna Preserve (1.7 mi / 2.8 km)
  • Pemaquid Beach Park (4.7 mi / 7.6 km)
  • Pemaquid Point Lighthouse Park (6.5 mi / 10.4 km)
  • Cabbage Island (9.2 mi / 14.8 km)
  • Linekin Bay (9.2 mi / 14.9 km)
  • Barrett Park (9.4 mi / 15.1 km)

How to get to and around Round Pond

The nearest airport is in Wiscasset, ME (ISS), located 12.7 mi (20.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Rockland, ME (RKD-Knox County Regional), which is 20.6 mi (33.2 km) away.

Frequently asked questions

What is the best area to stay in Round Pond when booking a holiday rental?
When considering a holiday rental in Round Pond, Maine, the area around the quaint village itself is an excellent choice. This charming coastal community offers a delightful blend of scenic beauty and local culture. Staying close to the waterfront gives you easy access to stunning views of the Round Pond and the surrounding landscapes.One of the highlights of this area is the picturesque Round Pond Harbor, where visitors can enjoy leisurely walks along the shore or observe local fishermen at work. Additionally, nearby attractions such as the Coastal Maine Botanical Gardens provide a lovely escape into nature, showcasing a diverse array of plants and beautiful pathways.In terms of accommodation, there are several properties available in Round Pond and its immediate vicinity, ranging from charming cottages to more spacious family homes. Each option typically offers a great experience, allowing visitors to immerse themselves in the tranquil surroundings.
Where are the best areas for renting a beach house in Round Pond?
For renting a beach house in Round Pond, Maine, the idyllic coastal areas along the Pemaquid Peninsula offer some of the best options. Properties near the Pemaquid Point Lighthouse provide stunning ocean views and easy access to rocky shores, where guests can enjoy tide pooling and picturesque sunsets. Many of these beach houses come equipped with amenities such as expansive decks, outdoor grilling areas, and well-appointed kitchens, superb for families or groups looking to enjoy a seaside retreat.In the charming village of Round Pond itself, you can find quaint cottages and larger homes that often feature private waterfront access. These accommodations typically include comfortable living spaces, outdoor seating, and sometimes even kayaks or paddleboards for exploring the calm waters of the harbour. The local area is also home to several artisanal shops and seafood restaurants, adding to the allure of a relaxing beach holiday.Additionally, the nearby Damariscotta Lake State Park offers opportunities for hiking and picnicking, making it a great spot for outdoor enthusiasts. Properties in this vicinity might include amenities such as fire pits and picnic areas, allowing guests to fully embrace the natural beauty of the region.
Where are the best Round Pond ski resort rentals?
For those seeking ski resort rentals near Round Pond, the closest significant ski area is the Camden Snow Bowl, located about 30 miles to the north. In the vicinity of Camden, travellers can find a range of accommodations, from cosy cabins to charming vintage inns. Many properties in this area come with convenient amenities such as wood-burning stoves, fully equipped kitchens, and access to outdoor decks, great for enjoying the beautiful Maine scenery after a day on the slopes.In Camden itself, visitors can explore local shops, cafes, and restaurants, enhancing their stay with a taste of the region's culture. Some rentals may be situated within walking distance of the town centre, offering a blend of convenience and scenic views of the Camden Hills. Additionally, there are options for larger group accommodations, including spacious homes with multiple bedrooms, ideal for families or friends travelling together.For those willing to venture a bit further, the Sugarloaf ski resort, one of the largest in the region, offers additional rental options. Around this area, travellers can find lodges and cabins that often feature ski-in/ski-out access, hot tubs, and communal spaces for relaxation after a day on the slopes.
What is the most popular type of holiday rental accomodation in Round Pond?
In Round Pond, holiday houses are the most popular type of holiday rental, with about 40 available throughout the area. These homes typically feature spacious interiors, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor decks, great for enjoying the picturesque views of the surrounding natural beauty. Alongside holiday houses, there are approximately 36 cottages that offer a charming, cosy atmosphere, often with rustic décor and proximity to the waterfront. For those seeking a more compact option, several apartments and cabins are also available, providing essential amenities for a comfortable stay.
Are there any family house rentals in Round Pond?
In Round Pond, Maine, there are some family-friendly house rentals available, with around 15 options to choose from. This charming coastal village offers a picturesque setting, superb for families looking to enjoy a holiday together. Many of these properties provide spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play safely.Visitors can explore nearby attractions such as the stunning Pemaquid Point Lighthouse or enjoy the sandy beaches along the coastline. The local area is also home to various recreational activities, including kayaking and hiking, ensuring that there's plenty to keep families entertained.
Are there pet-friendly house rentals in Round Pond?
In Round Pond, there are several pet-friendly house rentals available, offering a warm and welcoming atmosphere for travellers with furry companions. Many of these properties are situated near the picturesque coastline, providing easy access to scenic views and outdoor activities. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.The area itself is known for its charming village vibe, with local shops and eateries that often welcome pets. Additionally, the nearby Pemaquid Point Lighthouse and its surrounding parks present excellent opportunities for walks and exploration, making it a delightful destination for those looking to enjoy both nature and comfort while travelling with pets.
Are there any remote work holiday rentals in Round Pond?
In Round Pond, Maine, there is a good selection of remote work holiday rentals available, with around 76 options to choose from. This picturesque coastal area offers a tranquil environment great for working remotely while enjoying the beauty of nature. Many properties in this region come equipped with essential amenities such as reliable internet access, designated workspaces with desks and chairs, and printers, ensuring that all your work needs are met.The scenic surroundings also provide opportunities for relaxation after work hours, with nearby attractions including charming coastal views, local shops, and access to various outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Round Pond?
In Round Pond, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals and enjoy dining in comfort. Many properties also provide onsite parking for convenience. Outdoor spaces such as decks or patios are common, offering a pleasant area to relax and take in the scenic surroundings. Additionally, most rentals feature coffee and tea makers, ensuring that guests can start their day with a warm beverage.
When is the best time to visit Round Pond for a holiday rental?
The best time to visit Round Pond for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant time of year attracts families and outdoor enthusiasts alike, eager to take advantage of the warm weather and explore the beautiful coastal landscapes.During these summer months, temperatures typically range from a comfortable 15 to 30 degrees Celsius, superb for enjoying activities such as kayaking, fishing, and relaxing on the picturesque shores. The community comes alive with local events and festivals, offering plenty of opportunities for sightseeing and engaging with the friendly locals.For those looking for great value, consider visiting in November. This month presents a quieter experience, allowing you to appreciate the serene beauty of Round Pond as it transitions into winter. Enjoy peaceful walks along the shore and take in the stunning views without the hustle and bustle of peak tourist season.
What are the top attractions in Round Pond?
In Round Pond, Maine, visitors can enjoy a charming coastal experience with several attractions that highlight the area's natural beauty. The picturesque Round Pond Harbor is a focal point, where you can watch boats and enjoy fresh seafood at local eateries. The nearby Pemaquid Point Lighthouse, a historic site, offers stunning views of the Atlantic Ocean and is a popular spot for photography.For outdoor enthusiasts, the surrounding area provides opportunities for hiking and exploring nature, particularly at the Pemaquid Beach Park, which features sandy beaches and picnic areas. Additionally, the quaint village atmosphere of Round Pond is great for leisurely strolls, with unique shops and art galleries showcasing local crafts.The nearby town of Damariscotta, just a short drive away, is known for its charming shops and the Damariscotta River, where visitors can partake in kayaking and other water activities.
Are all fees included in the Round Pond holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Round Pond holiday homes with parking?
Stayz offers a wide selection of holiday homes in Round Pond with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Round Pond holiday homes?
You can find great discounts on holiday homes in Round Pond on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Round Pond holiday home booking on Stayz?
To find Round Pond holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Round Pond?
A long-stay holiday home in Round Pond is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Round Pond holiday home?
Book your Round Pond holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Round Pond?
Prices for holiday homes in Round Pond vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Round Pond to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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