Winter Harbor holiday rentals

We found 1,253 holiday rentals — enter your dates for availability
Discover a selection of 17 homes and other holiday rentals in Winter Harbor that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Winter Harbor

Showing deals for:25 Dec - 1 Jan

Private kitchen
Adirondacks on the shore- lobster boats, seals, eagles and coastal views.
Perched across from Acadia NP the cottage gets both ocean and mountain views.
Comfortable open floor plan for group gatherings
Exceptional
(101 reviews)

Waterfront Historic Maine Cottage • Private Shore • Acadia Views

Ellsworth

9% off
AU$5,615
for 7 nights, 1 cottage
AU$802 per night
includes taxes & fees
Waterfront Historic Maine Cottage • Private Shore • Acadia Views
Private kitchen
View from property
Interior
Dining
Exceptional
(35 reviews)

Designer Seal Harbor Home w/ Ocean Views in the heart of Acadia- sells out fast!

Seal Harbor

9% off
AU$18,568
for 7 nights, 1 home
AU$2,653 per night
includes taxes & fees
Designer Seal Harbor Home w/ Ocean Views in the heart of Acadia- sells out fast!
Exterior
Dome home interior, shows sleeping and living area for hanging out
Dome interior
Dome interior view - 15 ft ceilings
Exceptional
(50 reviews)

2-Acre DOME + Tiny House Cabin on OCEAN

Steuben

8% off
AU$4,003
for 7 nights, 1 cabin
AU$572 per night
includes taxes & fees
2-Acre DOME + Tiny House Cabin on OCEAN
Fire pit on deck over looking Acadia National Park
Living room off Kitchen, back door to hot tub on back deck
Interior
View of home and property.
Exceptional
(86 reviews)

Spacious Farmhouse with Mtn Views, quiet. Available year round.

Mount Desert

7% off
AU$6,421
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Spacious Farmhouse with Mtn Views, quiet. Available year round.
As seen from the shore at dusk
Lots of seating/lounging options--both on deck and nearby on granite ledge
photo taken from den—terraced down 2 steps, below main living area
view from Bedroom 1 (master-king bed)
Exceptional
(83 reviews)

Private Oceanfront "Coppertop" house, Acadia National Park

Mount Desert

8% off
AU$14,271
for 7 nights, 1 home
AU$2,039 per night
includes taxes & fees
Private Oceanfront "Coppertop" house, Acadia National Park
Living area
Interior
Dining
Private kitchen
Exceptional
(52 reviews)

Nestled between Bar Harbor and Acadia, a bright and spacious house in the woods

Bar Harbor

8% off
AU$4,640
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Nestled between Bar Harbor and Acadia, a bright and spacious house in the woods
Interior
Property grounds
lots of windows and seating in the sunroom - great to eat, relax or play games
enjoy sitting in the sunroom right off of the living area
Exceptional
(18 reviews)

Oceanfront Peaceful Getaway - close to Acadia's Schoodic Peninsula

Gouldsboro

8% off
AU$5,058
for 7 nights, 1 home
AU$723 per night
includes taxes & fees
Oceanfront Peaceful Getaway - close to Acadia's Schoodic Peninsula
Dining
Terrace/patio
Interior
Exterior
Exceptional
(50 reviews)

Pine Lodge: 2-bedroom vacation home minutes to Acadia National Park

Southwest Harbor

8% off
AU$3,844
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Pine Lodge: 2-bedroom vacation home minutes to Acadia National Park
Open kitchen (with large island), adjacent indoor dining and living room
Patio hammock for adult relaxation under deck
Exterior
Jordan Pond perimeter path is a favorite
Exceptional
(54 reviews)

A spacious sanctuary with 10+ private acres a few miles from Acadia NP entrance

Bar Harbor

8% off
AU$7,281
for 7 nights, 1 home
AU$1,040 per night
includes taxes & fees
A spacious sanctuary with 10+ private acres a few miles from Acadia NP entrance
Exterior
Property grounds
Living area
Interior
Exceptional
(44 reviews)

Spacious Home in the Heart of Acadia National Park

Bar Harbor

8% off
AU$4,647
for 7 nights, 1 home
AU$664 per night
includes taxes & fees
Spacious Home in the Heart of Acadia National Park
Interior
Living area
Dining
Private kitchen
Exceptional
(40 reviews)

Newly renovated in-town Bar Harbor, five bdrm apartment. Walk to shore & shops.

Bar Harbor

7% off
AU$4,236
for 7 nights, 1 home
AU$605 per night
includes taxes & fees
Newly renovated in-town Bar Harbor, five bdrm apartment. Walk to shore & shops.
Two Queen Beds
Living area
Exterior
Front Door
Exceptional
(48 reviews)

Perfectly Centered in Birch Harbor Village! Unit 4

Gouldsboro

8% off
AU$2,346
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Perfectly Centered in Birch Harbor Village! Unit 4
Kitchen all new with granite counter tops
Different view
Please look over Steve's ancient cans that he is so proud of 🤦🏼‍♀️
Both couches pull out into sleepers a queen and a twin sleeper
Exceptional
(59 reviews)

Quiet and located close to the ocean 2 bedroom 2 bath home

Steuben

8% off
AU$2,987
for 7 nights, 1 home
AU$427 per night
includes taxes & fees
Quiet and located close to the ocean 2 bedroom 2 bath home
Chart Room seafood restaurant and Frenchman Bay across the street.
Beach right across the street for your enjoyment!
Balcony overlooks the pool. Has chairs and tables
View from our balcony towards pool and ocean.
Exceptional
(112 reviews)

Ocean Views from every room. Enjoy nearby beach and Acadia National Park

Bar Harbor

8% off
AU$4,701
for 7 nights, 1 home
AU$672 per night
includes taxes & fees
Ocean Views from every room. Enjoy nearby beach and Acadia National Park
Interior
Living area
Property grounds
Terrace/patio
Exceptional
(40 reviews)

Perfectly centered in the Birch Harbor Village!

Birch Harbor

8% off
AU$1,972
for 7 nights, 1 apartment
AU$282 per night
includes taxes & fees
Perfectly centered in the Birch Harbor Village!
Lobby
Town pier- Stewman lobster on the left
Dining
Private kitchen
Exceptional
(34 reviews)

Steps to Restaurants, Shops & Waterfront, Bar Island, Free 2-car Parking, Wi-fi

Bar Harbor

8% off
AU$5,428
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Steps to Restaurants, Shops & Waterfront, Bar Island, Free 2-car Parking, Wi-fi
Living area
Private kitchen
Room
Exterior
Exceptional
(89 reviews)

Recently Renovated In-Town Bar Harbor 4 Bed 3 Bth Apartment with Private Parking

Bar Harbor

11% off
AU$4,332
for 7 nights, 1 apartment
AU$619 per night
includes taxes & fees
Recently Renovated In-Town Bar Harbor 4 Bed 3 Bth Apartment with Private Parking
Interior
Living area
Private kitchen
Dining
Exceptional
(100 reviews)

Nut Hatch—3BR Bar Harbor Home, Walkable to Downtown and Acadia, Pet Friendly

Bar Harbor

8% off
AU$4,533
for 7 nights, 1 apartment
AU$648 per night
includes taxes & fees
Nut Hatch—3BR Bar Harbor Home, Walkable to Downtown and Acadia, Pet Friendly
Bathroom
Private kitchen
Living area
Dining
Exceptional
(48 reviews)

Recently renovated 3Bdm 2Bth APT in downtown Bar Harbor/Acadia National Park

Bar Harbor

7% off
AU$3,706
for 7 nights, 1 apartment
AU$529 per night
includes taxes & fees
Recently renovated 3Bdm 2Bth APT in downtown Bar Harbor/Acadia National Park
Private kitchen
Exterior detail
Interior
Living area
Exceptional
(61 reviews)

1-BR apt 0.5-mile to Acadia National Park & 1-mile to downtown

Bar Harbor

8% off
AU$2,186
for 7 nights, 1 apartment
AU$312 per night
includes taxes & fees
1-BR apt 0.5-mile to Acadia National Park & 1-mile to downtown

  • 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

Delight in the waterfront landscape of Winter Harbor

Enjoy the musicals and other features of Winter Harbor. This city's seafood restaurants, golfing and boating draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winter Harbor

Are you hoping to discover things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Winter Harbor a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bar Harbor Whale Watch Co (6 mi / 9.7 km)
  • Kebo Valley Golf Club (7 mi / 11.2 km)
  • Grindstone Neck Golf Course (0.7 mi / 1.2 km)
  • Bartlett Maine Estate Winery (6.1 mi / 9.8 km)
  • Heart of Acadia Loop (8.4 mi / 13.5 km)
  • Bubble Rock (9.7 mi / 15.7 km)

Exploring the natural landscape of Winter Harbor

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

  • Acadia National Park (10.2 mi / 16.4 km)
  • Schoodic Peninsula (2.3 mi / 3.7 km)
  • Schoodic Point (4.4 mi / 7.1 km)
  • Shore Path (6 mi / 9.6 km)
  • Agamont Park (6 mi / 9.7 km)
  • Village Green (6 mi / 9.7 km)

Transport options to and around Winter Harbor

The nearest airport is in Bar Harbor, ME (BHB-Hancock County - Bar Harbor), located 14.2 mi (22.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in Winter Harbor when booking a holiday rental?
When considering a holiday rental in Winter Harbor, Maine, the best area to stay in is near the picturesque harbour itself. This charming neighbourhood offers a serene atmosphere with stunning waterfront views that capture the essence of coastal Maine. Staying close to the harbour provides easy access to some of the area's top attractions, such as the breathtaking Acadia National Park, which is just a short drive away. This park is renowned for its dramatic landscapes, including rugged coastlines and lush woodlands, making it a favourite spot for outdoor enthusiasts.In addition to the natural beauty, the local area boasts quaint shops and delightful eateries that serve fresh seafood and other regional specialities. You'll find a variety of holiday rental properties here, suiting different tastes and budgets, each providing a unique opportunity to immerse yourself in the local culture.
Where are the best areas for renting a beach house in Winter Harbor?
For renting a beach house in Winter Harbor, the scenic waterfront along the Frenchman Bay is an excellent choice. This area offers stunning views of the surrounding islands and easy access to sandy beaches, making it ideal for beach lovers. Properties here typically come with amenities such as spacious decks for enjoying the sunset, outdoor grills for barbecuing, and fully equipped kitchens that cater to families or groups. Many rentals also feature cosy living areas with fireplaces, superb for cooler evenings.Additionally, the nearby Schoodic Peninsula provides a more secluded experience with its rugged coastline and natural beauty. Rentals in this vicinity often include features like private beach access, garden spaces for outdoor activities, and sometimes even kayaks or bicycles for exploring the stunning landscapes. The area is known for its tranquillity and proximity to nature, with opportunities for hiking and bird-watching in the Acadia National Park.
What is the most popular type of holiday rental accomodation in Winter Harbor?
In Winter Harbor, holiday houses are the most common type of holiday rental, with around 48 available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, fully furnished kitchens, and living areas that provide a comfortable home-away-from-home experience. Many holiday houses also come with outdoor spaces, great for enjoying the picturesque views of the surrounding nature.Cottages are another popular option, with about 21 available, offering a charming and rustic atmosphere. They often include amenities such as kitchenettes and cosy living spaces, ideal for couples or small families looking for a quaint retreat.
Are there any family house rentals in Winter Harbor?
In Winter Harbor, Maine, there are numerous family-friendly house rentals available, with around 15 options to choose from. This charming coastal town offers a variety of accommodations suitable for families, often featuring spacious living areas, fully equipped kitchens ideal for preparing meals together, and outdoor spaces great for children to play. Many properties also include amenities such as Wi-Fi and laundry facilities, ensuring a convenient and comfortable stay.Visitors can enjoy the stunning natural beauty of the area, as Winter Harbor is located near Acadia National Park, where families can explore hiking trails, picturesque landscapes, and scenic views. Additionally, the nearby Schoodic Peninsula offers opportunities for stunning coastal walks and wildlife viewing, making it a great spot for family outings.
Are there pet-friendly house rentals in Winter Harbor?
In Winter Harbor, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. This charming coastal town is known for its scenic beauty and proximity to Acadia National Park, which offers ample opportunities for outdoor adventures with your furry friends.Many of the holiday homes in Winter Harbor come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Some properties may include features like fire pits or private decks, great for relaxing after a day of exploration.The nearby Schoodic Peninsula, part of Acadia National Park, is particularly top for its stunning coastal views and hiking trails, allowing for enjoyable walks with pets.
Are there any remote work holiday rentals in Winter Harbor?
In Winter Harbor, there are numerous remote work holiday rentals available, with around 69 options to choose from. This picturesque coastal town offers a tranquil environment that is conducive to productivity. Many of these properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable living spaces designed for both relaxation and work.Visitors can enjoy the stunning views of the surrounding landscapes, with the nearby Acadia National Park providing opportunities for outdoor activities during breaks. The area features charming local eateries and shops, ensuring that everything you need is within reach. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winter Harbor?
In Winter Harbor, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties feature decks or patios where visitors can enjoy the serene surroundings. A fireplace is a common addition, providing warmth and a cosy atmosphere during the cooler months. Onsite parking is typically available, ensuring convenience for those travelling by car. Additionally, most rentals come with a coffee and tea maker for a comforting start to the day.
When is the best time to visit Winter Harbor for a holiday rental?
The most popular time to visit Winter Harbor is during the summer months of June to August, when the coastal charm truly comes alive. This peak season invites travellers seeking outdoor adventures, with opportunities for kayaking, hiking, and exploring Acadia National Park. The weather is typically warm, with temperatures ranging from 15 to 25 degrees Celsius, making it ideal for enjoying the stunning landscapes and vibrant local culture.July stands out as the most popular month, with a lively option as families and outdoor enthusiasts gather to soak up the sun and partake in various activities. Visitors can explore the picturesque shores, indulge in fresh seafood, and attend local events that celebrate the region's heritage.For those who prefer a quieter experience and are looking for better value, November is an excellent choice. While the weather turns cooler, this transitional month allows for peaceful walks along the coastline and an opportunity to witness the beautiful autumn colours without the crowds. It's a great time for photography and enjoying the serene beauty of nature.Ultimately, the best time to book your holiday rental in Winter Harbor hinges on whether you're drawn to the vibrant energy of summer or the tranquil charm of the shoulder season.
What are the top attractions in Winter Harbor?
In Winter Harbor, visitors can enjoy a variety of attractions that highlight the area's natural beauty and coastal charm. A major draw is the Schoodic Peninsula, part of Acadia National Park, which offers stunning views of the rugged coastline, hiking trails, and opportunities for birdwatching. The nearby Winter Harbor Lighthouse, a picturesque landmark, is worth a visit for its scenic surroundings.The town itself features quaint shops and galleries that showcase local art and crafts, providing a taste of the community's culture. The local seafood restaurants offer fresh catches, giving visitors a chance to indulge in the region's culinary delights. For those interested in marine activities, the nearby waters are superb for kayaking and exploring the serene bays and coves.Additionally, the annual Winter Harbor Lobster Festival draws crowds, celebrating the local fishing industry and offering a chance to experience the vibrant community spirit.
Are all fees included in the Winter Harbor 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 Winter Harbor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winter Harbor 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 Winter Harbor holiday homes?
You can find great discounts on holiday homes in Winter Harbor 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 Winter Harbor holiday home booking on Stayz?
To find Winter Harbor 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 Winter Harbor?
A long-stay holiday home in Winter Harbor 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 Winter Harbor holiday home?
Book your Winter Harbor 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 Winter Harbor?
Prices for holiday homes in Winter Harbor 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 Winter Harbor 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.

More holiday ideas