Photo by Marc Maheu

Oakland Holiday Rentals

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Holiday Rentals in Oakland

Central Maine Apartment offering 4 Seasons of Fun.
Smart TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, (30)
"This property is Fantastic! All the comforts of home, with amenities we did not expect. Some food items in cupboard(soup, oatmeal,pancake mix…) Eggs, butter, milk, water, apple sauce in fridge! A fully stocked kitchen with silverware, pots, pans, and all kinds kitchen appliances. Even a bottle of wine! Comfy bed and bathroom was stocked with all necessities, in case you forgot anything! Plush bath towels, body wash, shampoo, and conditioner. Hosts were very fast to respond to all questions. They...
The price is AU$379
includes taxes & fees
25 Sept - 26 Sept
Central Maine Apartment offering 4 Seasons of Fun.
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, (47)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
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
8.6 out of 10, Excellent, (11)
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
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!
9.8 out of 10, Exceptional, (6)
"This was a great place! Super close walk to a beautiful lake. Everything we possibly needed in the house. The host was wonderful and helpful. The kids favorite part was the kayaking the lake! Thank you!!"
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
9.2 out of 10, Wonderful, (17)
"Absolutely beautiful house on the lake. Enjoyed this with my husband and cousins. Just as described. Responsive host."
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Exterior
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
9.8 out of 10, Exceptional, (23)
"This was an amazing experience and the vision that the owners have is amazing I highly recommend this place"
The price is AU$244
includes taxes & fees
8 Oct - 9 Oct
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
The Cabin Skowhegan
Property grounds
The Cabin Skowhegan
9.6 out of 10, Exceptional, (34)
"Only spent a short amount of time here, cute stop over!"
The price is AU$278
includes taxes & fees
3 Oct - 4 Oct
The Cabin Skowhegan
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.
9.4 out of 10, Exceptional, (118)
"Camp was as advertised. Owner very friendly and helpful. Nice quiet location and clean."
The price is AU$241
includes taxes & fees
1 Oct - 2 Oct
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
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, (108)
"We absolutely cherished our time at the cabin, and hope to return! "
Private three season cabin nestled in woods on shore of pristine Maine lake
The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds
The Cabbage on Olive Street, overlooking Hayden Brook
8.8 out of 10, Excellent, (8)
"We enjoyed our stay at The Cabbage. The Host is very accommodating. Someone had recently given a bad review. We didn't experience any of the things they had. The cabin is old with some modern updates, mostly in the bathroom and the sleeping loft. It's extremely cute. It's a seasonal camp/cabin. Go expecting a rustic Maine cabin experience and you will fully enjoy your stay at the Cabbage."
The Cabbage on Olive Street, overlooking Hayden Brook
Cozy Lake House on Cobbosseeconte Lake
Outdoor dining
Cozy Lake House on Cobbosseeconte Lake
10.0 out of 10, Exceptional, (45)
"Thoroughly enjoyed our stay and accommodations. "
The price is AU$788
includes taxes & fees
24 Sept - 25 Sept
Cozy Lake House on Cobbosseeconte 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
8.0 out of 10, Very good, (14)
"Beautiful place. Loons, eagles, Ospreys, and good fishing. No A/C made a couple of days miserable when heat and humidity was in the mid-nineties. Many fans available, though. Would be more ethical to let people know before booking that tap water is not drinkable. Saying a kayak is available is a bit of a stretch (small plastic boat)."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Property grounds
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
10.0 out of 10, Exceptional, (10)
"We were introduced to the Belgrade Lakes 15 years ago when our daughter went to summer camp in the area. We've been going back ever since because of all the incredible Mainers we met over the years and because Maine really is its own kind of vacationland. The Guest House where we had stayed closed and we always wanted to rent our own place to continue visiting and to share with family and friends. This lake house was absolutely perfect for us. It was exceptionally clean upon arrival, all...
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
Property grounds
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
10.0 out of 10, Exceptional, (10)
"Lou-Anne and Rick were extremely helpful and accommodating. The cabin was immaculate, well-appointed, and picturesque. We asked to bring our small boat and they helped us with logistics and navigation of the ponds. Lots of fish and fun. Our family our last gasp of summer ."
Cozy cabin on a peaceful pond. Enjoy the amenities of the Kennebec Valley Area.
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (155)
"We spent a week at this beautiful home and had a wonderful time. We took our bass boat and were able to launch it right on the property and tie it which was really convenient! We went fishing off and on all week on this beautiful lake. There were loons everywhere! Their calls are just entrancing."
Cottage on Cobbosseecontee Lake. Dates available.
Sunset Chalet- Stylish Waterfront Gem
Fridge, microwave, stovetop, coffee/tea maker
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, (21)
"The property was beautiful, the cottage was clean and inviting."
The price is AU$1,357
includes taxes & fees
30 Sept - 1 Oct
Sunset Chalet- Stylish Waterfront Gem
Nature lovers Paradise your own island
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, (64)
"I have visited this idyllic spot about 10-12 times, and each time I am reminded of why I love it so much: the feeling of isolation on your own private island, the company of the cheerful small birds, the magnificent osprey family in the tallest tree (their nest is a few feet from the cabin), the view down the lake from the porch and living area, the curtain of trees surrounding the cabin, the warm water for swimming, the calm quiet at night, and the parade of ducks and loons nearby. And I...
Nature lovers Paradise your own island
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Exterior
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
10.0 out of 10, Exceptional, (24)
"Lovely cabin. A little more finishing work needed in the outside but inside great. Well appointed, wonderful wood work and amazing lake views. We were here for dinner at the Lost Kitchen and these accommodations added to an amazing experience. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
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, (22)
"Loved the house / views / lake side hangout. Property was amazing and absolutely would consider going back. "
Lakefront, Stunning Home only 30 min to Sugarloaf!
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
TV, DVD player, books
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
8.8 out of 10, Excellent, (6)
"Peaceful and relaxing. A few things would have been nice to know ahead of our trip. Difficult to get to the water to swim. Did not know when trash pick up was scheduled and had to remind owner that it was not picked up. All that being said - it was very enjoyable"
Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK
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.
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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
8.6 out of 10, Excellent, (11)
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
Smart TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, (30)
"This property is Fantastic! All the comforts of home, with amenities we did not expect. Some food items in cupboard(soup, oatmeal,pancake mix…) Eggs, butter, milk, water, apple sauce in fridge! A fully stocked kitchen with silverware, pots, pans, and all kinds kitchen appliances. Even a bottle of wine! Comfy bed and bathroom was stocked with all necessities, in case you forgot anything! Plush bath towels, body wash, shampoo, and conditioner. Hosts were very fast to respond to all questions. They...
The price is AU$379
includes taxes & fees
25 Sept - 26 Sept
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!
9.8 out of 10, Exceptional, (6)
"This was a great place! Super close walk to a beautiful lake. Everything we possibly needed in the house. The host was wonderful and helpful. The kids favorite part was the kayaking the lake! Thank you!!"
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.

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 22 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.