Photo by Marc Maheu

Oakland Holiday Rentals

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Holiday Rentals in Oakland

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, 42 reviews
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Fridge, microwave, oven, stovetop
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
7.8 out of 10, Good, 6 reviews
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, 25 reviews
"This was such an awesome place To stay. They had snacks and coffee. Enjoyed all the special touches!"
The price is NZ$423
includes taxes & fees
2 Jul - 3 Jul
Central Maine Apartment offering 4 Seasons of Fun.
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Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Property grounds
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
10.0 out of 10, Exceptional, 1 review
"We thoroughly enjoyed our stay at this property. Beautiful location and full amenities. The house was spotless. The beds were comfortable and linens drop drawer. Mala was easy to communicate with. Suggested more trash barrels. Only surprise was inability to flush any paper due to septic system. We survived our American hesitations. I’ve traveled in Africa and Russia where this was the norm. Great rental."
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Fridge, microwave, oven, stovetop
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
9.6 out of 10, Exceptional, 13 reviews
"Kamp Kota is exactly as advertised. The location is peaceful, and the fenced yard was perfect for our pups. We will be back!"
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds
The Cabbage on Olive Street, overlooking Hayden Brook
10.0 out of 10, Exceptional, 3 reviews
"Met our needs very well located. We would certainly recommend for future use"
The Cabbage on Olive Street, overlooking Hayden Brook
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
10.0 out of 10, Exceptional, 107 reviews
"Peter and Jane are terrific hosts of a beautiful spot on the lake. We did all the things. We hiked Mt. Blue to the top. We peddled the boat out onto the lake. We watched the sunrise and sunset on the screened in porch. We made fires and roasted marshmallows. We had a terrifically beautiful family vacation at this perfect little cottage on the lake."
Getaways, Vacation, UMF, FMH Hospital, Skiing, Fishing, 4 Season, Traveling Prof
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
9.6 out of 10, Exceptional, 107 reviews
"We loved staying at Tom’s cottage. It was cozy and warm and had everything we needed. Tom is a great host, enjoyed chatting with him. We will definitely rent here again!!"
The price is NZ$301
includes taxes & fees
5 Jun - 6 Jun
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.4 out of 10, Very good, 6 reviews
"Myself and 4 friends booked this home on the water for an annual super bowl ice fishing trip. The house was just as described, spacious and comfortable. The pond is beautiful and the fishing was outstanding, we caught fish all day long. Location is good as well, with plenty of restaurants and downtown Augusta within 10 to 15 minutes. Great home for the price."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
Exterior
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
Free private parking, for multiple vehicles.
Property grounds
Free private parking, for multiple vehicles.
9.6 out of 10, Exceptional, 25 reviews
"Larry was a wonderful host. This cabin housed us 5 women for night comfortably. Looking forward to coming back next year."
The price is NZ$273
includes taxes & fees
9 Jun - 10 Jun
Free private parking, for multiple vehicles.
Lakefront, Stunning Home only 30 min to Sugarloaf!
View from property
Lakefront, Stunning Home only 30 min to Sugarloaf!
10.0 out of 10, Exceptional, 17 reviews
"My husband, two dogs, and I enjoyed a quiet April weekend on Porter Lake. The place was exactly as described and clearly a beloved family lake house. We will certainly be back!"
Lakefront, Stunning Home only 30 min to Sugarloaf!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
10.0 out of 10, Exceptional, 51 reviews
"The property was just as described and we enjoyed the peace and quiet. The cabin is beautiful and very well appointed. I would definitely recommend it to friends."
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Three waterfront cottages with private sandy beach - Family Getaway
On the beach
Three waterfront cottages with private sandy beach - Family Getaway
10.0 out of 10, Exceptional, 20 reviews
"WE HAD AN AMAZING STAY! MOST ENJOYABLE AND BEAUTIFUL PROPERTY"
Three waterfront cottages with private sandy beach - Family Getaway
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
Fridge, microwave, oven, stovetop
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
7.8 out of 10, Good, 10 reviews
"The house and surrounding were very nice. Exactly as described and had some nice touches left by the management company- extra soap, laundry pods, doggie poop bags. The only concerns were that the keypad on the door was temperamental and didn’t work our entire visit (thankfully there was a key in a lockbox so we could get inside when it was cold and raining) and there were several dishes put away dirty. Overall it was a great property that we hope to return to in warmer weather and enjoy the...
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
Sunset Chalet- Stylish Waterfront Gem
Fridge, microwave, stovetop, coffee/tea maker
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, 20 reviews
"This is by far one of the best places we’ve stayed. From the beautiful decor, exposed wood and cozy fireplace. It was the attention to detail and small little extras that made this an extra special visit. The serene music playing as you enter the home to the specialized note and picnic basket! They are very accommodating to any situation that may arise and communicate on a five star level. An amazing stay and will be visiting again!"
The price is NZ$1,452
includes taxes & fees
5 Jun - 6 Jun
Sunset Chalet- Stylish Waterfront Gem
Nature lovers Paradise your own island
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, 59 reviews
"This is our third summer staying here for a week and it was perfect as usual! Thanks Deb!"
Nature lovers Paradise your own island
Private three season cabin nestled in woods on shore of pristine Maine lake
Exterior
Private three season cabin nestled in woods on shore of pristine Maine lake
9.8 out of 10, Exceptional, 100 reviews
"Easy"
Private three season cabin nestled in woods on shore of pristine Maine lake
Family and pet friendly ME cabin, private, Trails, close to town.
Fridge, microwave, oven, stovetop
Family and pet friendly ME cabin, private, Trails, close to town.
10.0 out of 10, Exceptional, 21 reviews
"We enjoyed our stay at the cabin--everything was very clean and well organized, with coffee and tea, all the utensils and pots one would need. The beds were comfortable and there were lots of towels. We especially enjoyed the fact that there was a fire pit--lovely for a warm evening. We were able to get back and forth to Colby College in 30 minutes and had dinner in Skowhegan."
The price is NZ$599
includes taxes & fees
26 Jun - 27 Jun
Family and pet friendly ME cabin, private, Trails, close to town.
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Property grounds
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
7.6 out of 10, Good, 22 reviews
"The location of King’s Kastle on Salmon Lake is excellent. The lake is wide at that point and offers great views of the sunrise, particularly from the upstairs master bedroom suite. The lake has less development than others where we have stayed in Maine. We enjoyed seeing loons, eagles, and osprey which are abundant. We went in the latter part of August when the kids’ summer camps had closed, which reduced boat traffic. The cottage is roomy and has a long list of amenities. All appliances were...
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Don't see what you're looking for?
See all available properties in Oakland
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.

Other types of properties in Oakland you may be interested in

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Fridge, microwave, oven, stovetop
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
7.8 out of 10, Good, 6 reviews
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, 25 reviews
"This was such an awesome place To stay. They had snacks and coffee. Enjoyed all the special touches!"
The price is NZ$423
includes taxes & fees
2 Jul - 3 Jul
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
Property grounds
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
10.0 out of 10, Exceptional, 1 review
"We thoroughly enjoyed our stay at this property. Beautiful location and full amenities. The house was spotless. The beds were comfortable and linens drop drawer. Mala was easy to communicate with. Suggested more trash barrels. Only surprise was inability to flush any paper due to septic system. We survived our American hesitations. I’ve traveled in Africa and Russia where this was the norm. Great rental."
Cozy Long Pond cottage, private mooring and community beach. Bring your boat!
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland. Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Oakland is known for its shopping and restaurants. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Oakland has to offer?

Cozy Long Pond cottage, private mooring and community beach. Bring your boat!: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Our travellers also rate Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 21 Expedia holiday rentals in Oakland for a memorable holiday.

What can I see and do in Oakland?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Belgrade Lakes Chain. Colby College and Tree Spirits are a couple of places you'll find in the wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.

Recent reviews of Oakland properties
Expedia verified reviews

Senator Inn & Spa

Senator Inn & Spa

5/5 Excellent
Great Stay
"Larger, comfortable king room with fold out couch. Mini fridge with freezer for our frozen ice packs & a great pool with hot tub. Very good restaurant for breakfast. "
A verified traveller stayed at Senator Inn & Spa
Posted 3 days ago
Senator Inn & Spa