Oakland holiday rentals

We found 205 holiday rentals — enter your dates for availability
Select from 31 homes, 16 cottages and other holiday rentals in Oakland to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and hot tub. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Choose a holiday rental for your Oakland getaway

Enjoy the monuments and other features of Oakland. This city is well-known for its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Oakland

Are you looking for top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that makes Oakland a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Belgrade Lakes Golf (8.1 mi / 13 km)
  • Augusta Country Club (16.9 mi / 27.2 km)
  • Natanis Golf Course (8.8 mi / 14.2 km)
  • Eaton Mountain (16.4 mi / 26.4 km)
  • Titcomb Mountain Ski Area (23.2 mi / 37.4 km)
  • Spruce Mountain Jay (24.2 mi / 39 km)

Exploring the natural features in Oakland

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

  • Kennebec River (4.8 mi / 7.7 km)
  • Belgrade Lakes Chain (5.9 mi / 9.6 km)
  • China Lake (10.7 mi / 17.2 km)
  • Echo Lake (16.2 mi / 26.1 km)
  • Maranacook Lake (17.8 mi / 28.7 km)
  • Cobbosseecontee Lake (22.7 mi / 36.5 km)

How to get to and around Oakland

Fly into Waterville, ME (WVL-Robert Lafleur), the closest airport, located 2.1 mi (3.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Augusta, ME (AUG-Augusta State), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the best area to stay in Oakland when booking a holiday rental?
When considering a holiday rental in Oakland, Maine, the area around the picturesque Messalonskee Lake is a delightful choice. This neighbourhood offers a serene lakeside experience, making it ideal for those who enjoy outdoor activities such as kayaking, fishing, and hiking. The natural beauty of the lake provides a great backdrop for relaxation and recreation.Another excellent option is the vicinity of downtown Oakland, where visitors can engage in the local culture. This area boasts charming shops and eateries, providing a taste of the community spirit. One great attraction nearby is the Oakland Town Park, which features beautiful walking trails and picnic areas, great for families and those looking to enjoy a leisurely day outdoors.While the number of properties available can vary, the selections in these areas often cater to a range of preferences, from cosy cabins to more spacious homes, making it convenient for different group sizes and types of holidays.
Where are the best areas for renting a beach house in Oakland?
For renting a beach house in Oakland, Maine, the area around the eastern shore of Lake Messalonskee is particularly appealing. Here, visitors can find a variety of properties that offer stunning lake views and direct access to the water. Many of these rentals come with amenities such as private docks, outdoor seating areas, and fully equipped kitchens, which make them great for families or groups looking to enjoy lakeside living.Additionally, the neighbourhood near Oakland's public beaches, such as the one at the Oakland Recreation Area, provides further options for beach house rentals. These properties often feature spacious decks for entertaining, barbecue facilities, and easy access to swimming and recreational activities. The proximity to local shops and dining options adds convenience for travellers, ensuring everything is within reach.For those interested in exploring the outdoors, the nearby Kennebec River offers opportunities for boating and fishing, while the surrounding area is great for hiking and enjoying nature. Rentals in this region typically include essential amenities such as heating, Wi-Fi, and comfortable living spaces designed for relaxation after a day of adventure.
Where are the best Oakland ski resort rentals?
For skiing in Oakland, Maine, the nearby Sugarloaf Mountain Resort offers the best options for rentals. The town of Carrabassett Valley, which is just a short drive from Oakland, is an excellent place to find accommodations close to the ski slopes. Here, you'll find a variety of properties ranging from cosy cabins to spacious lodges, many of which come equipped with amenities such as fully stocked kitchens, fireplaces, and hot tubs, great for relaxing after a day on the mountain.In Carrabassett Valley, some rentals are conveniently located near local eateries and shops, providing easy access to dining and supplies. Additionally, properties often feature ski-in/ski-out access, allowing guests to hit the slopes directly from their doorstep. The area is also known for its breathtaking views of the surrounding mountains, and many rentals include outdoor spaces where guests can enjoy the scenic beauty.Moreover, the region offers various recreational activities beyond skiing, including snowshoeing and snowmobiling trails.
What is the most popular type of holiday rental accomodation in Oakland?
In Oakland, holiday houses are the most popular type of holiday rental, with around 52 available across the area. These homes typically offer spacious living areas, fully equipped kitchens, and multiple bedrooms, making them ideal for families or groups looking for a comfortable stay. Additionally, there are about 30 cabins, which provide a charming rustic experience, often featuring wood-burning stoves and proximity to nature, superb for those wanting to immerse themselves in the scenic beauty of the region. Cottages, numbering around 22, offer a quaint and cosy atmosphere, often equipped with small kitchens and outdoor spaces for relaxation. Finally, there are approximately 18 apartments, usually found in more populated areas, providing convenient access to local amenities and attractions.
Are there any family house rentals in Oakland?
In Oakland, Maine, there are numerous family-friendly holiday rentals available, with around 48 properties to choose from. This charming area offers a variety of options suitable for families, including homes with spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces for children to enjoy. Many of these rentals also feature amenities like Wi-Fi and laundry facilities, ensuring a convenient and comfortable stay.Visitors can explore the nearby Messalonskee Lake, superb for swimming, fishing, and boating, while the scenic views and surrounding nature make for delightful family outings. Additionally, the local parks provide playgrounds and picnic areas, ideal for spending quality time outdoors.
Can I rent a holiday home with a pool or hot tub in Oakland?
In Oakland, Maine, there are several holiday homes available for rent that come with pools or hot tubs, providing a great option for those looking to relax and unwind. The area features charming properties, often set in tranquil surroundings that allow guests to enjoy a peaceful retreat. Many of these rentals are spacious and equipped with amenities such as fully stocked kitchens, outdoor decks, and private outdoor spaces ideal for family gatherings or socialising with friends.Oakland's proximity to nearby lakes, such as Messalonskee Lake, also offers additional recreational opportunities, allowing guests to combine the enjoyment of a pool or hot tub with activities like swimming, kayaking, and fishing.
Are there pet-friendly house rentals in Oakland?
In Oakland, Maine, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these rentals come equipped with amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making them suitable for families or groups looking for a comfortable stay.The area itself offers a serene setting with opportunities for outdoor activities, and nearby lakes provide excellent spots for walking and enjoying nature with pets. Oakland is also close to local parks, which can be great for leisurely strolls or picnics.
Are there any remote work holiday rentals in Oakland?
In Oakland, Maine, there are numerous remote work holiday rentals available, with around 114 options to choose from. This charming town, known for its natural beauty and proximity to the Belgrade Lakes, offers a variety of properties suitable for those looking to balance work and leisure. Many of these rentals come equipped with essential amenities for remote work, such as free Wi-Fi, dedicated desk spaces, and comfortable seating arrangements, ensuring a productive environment.Travellers can find accommodations that range from cosy cabins to spacious homes, often featuring outdoor spaces where one can unwind after a day of work. With the serene landscapes of Maine providing a great backdrop, these rentals allow guests to enjoy the tranquility of the area, while still being close to local attractions. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oakland?
In Oakland, Maine, popular rental amenities include kitchens, which allow guests to prepare their own meals and enjoy a homely dining experience. Many rentals also feature decks or patios, providing a great outdoor space to relax and soak in the surroundings. Onsite parking is a common convenience, making it easier for travellers to explore the area without worrying about finding parking. Additionally, most accommodations offer coffee and tea makers, ensuring guests can enjoy their morning brews at their leisure.
When is the best time to visit Oakland for a holiday rental?
July is the most popular time to visit Oakland, Maine, when the region truly comes alive with summer activities. This peak season, spanning from June to August, attracts travellers, eager to enjoy the beautiful lakes, hiking trails, and vibrant community events. With warm temperatures typically ranging from 15 to 30 degrees Celsius, visitors can comfortably partake in outdoor pursuits such as kayaking, fishing, or simply relaxing by the water.If you're seeking a more tranquil experience, consider visiting in September. This month offers a wonderful opportunity to witness the stunning early autumn foliage as the leaves begin to change colour, creating an enchanting backdrop for hiking and sightseeing. The milder temperatures—around 10 to 20 degrees Celsius—make it an ideal time for those who prefer pleasant weather without the summer crowds.Ultimately, your choice of when to visit Oakland will depend on whether you prefer the lively option of peak summer or the peaceful charm of early autumn.
What are the top attractions in Oakland?
In Oakland, Maine, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. One of the main draws is Messalonskee Lake, which offers opportunities for swimming, fishing, and boating, making it a popular spot for outdoor enthusiasts. The lake is surrounded by several parks and walking trails, providing a serene environment for picnics and leisurely strolls.The quaint downtown area features local shops and eateries, great for experiencing the community's vibe. Additionally, the nearby Belgrade Lakes region offers stunning views and recreational activities, including hiking and golfing. For those interested in history, the Oakland Historical Society provides insights into the local heritage.
Are all fees included in the Oakland 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 Oakland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakland 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 Oakland holiday homes?
You can find great discounts on holiday homes in Oakland 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 Oakland holiday home booking on Stayz?
To find Oakland 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 Oakland?
A long-stay holiday home in Oakland 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 Oakland holiday home?
Book your Oakland 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 Oakland?
Prices for holiday homes in Oakland 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 Oakland 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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