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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

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

9.4 out of 10, Exceptional, (59)
"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
Central Maine Apartment offering 4 Seasons of Fun.
Property grounds

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (39)
"Cozy, quiet, clean, close to family and affordable"
The price is HK$820
HK$1,924 total
includes taxes & fees
1 Sept - 2 Sept
Central Maine Apartment offering 4 Seasons of Fun.
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is HK$942
HK$1,802 total
includes taxes & fees
28 Aug - 29 Aug
Sister A-Frame in Woods B
Belgrade Lake house with Dock!
Fridge, microwave, oven, stovetop

Belgrade Lake house with Dock!

10.0 out of 10, Exceptional, (1)
"This property was so peaceful and quiet. It sits on a large lot with lots of privacy. The walk down to the dock is fun for kids, lots of rocks and it’s a little trail. We spent most of our time down at the dock. The views were spectacular, beautiful reflections in the water each morning, calm quiet lake and the sunset right in front of us each night. It wasn’t buggy and we used the kayak, but wear water shorts bc it does take in some water. We also brought our own paddle board and would highly...
Belgrade Lake house with Dock!
Classic and adorable Maine camp on North Pond in the Belgrade Lakes
Exterior

Classic and adorable Maine camp on North Pond in the Belgrade Lakes

10.0 out of 10, Exceptional, (31)
"Beautiful cabin in an idyllic location! We always enjoy our week at Blessings and hope to return!"
Classic and adorable Maine camp on North Pond in the Belgrade Lakes
The Modern Maine Retreat
Dining

The Modern Maine Retreat

8.6 out of 10, Excellent, (10)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Beach towels

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

9.2 out of 10, Wonderful, (17)
"Great location and wonderful hosts!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Charming Guest House on Farm - Near lakes and trails
TV

Charming Guest House on Farm - Near lakes and trails

10.0 out of 10, Exceptional, (4)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
The price is HK$1,618
HK$2,690 total
includes taxes & fees
2 Sept - 3 Sept
Charming Guest House on Farm - Near lakes and trails
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!
Exterior

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

9.0 out of 10, Wonderful, (23)
"We had an amazing week. This is the perfect lake cabin… swimming, boating, tubing, campfires at night… we even used a projector to do an outdoor movie night. The owners are very responsive and helpful. We would definitely stay here again."
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.2 out of 10, Wonderful, (23)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is HK$1,019
HK$2,491 total
includes taxes & fees
27 Aug - 28 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
Nature lovers Paradise your own island
Exterior

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (67)
"Amazing property! "
Nature lovers Paradise your own island
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Exterior

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

9.4 out of 10, Exceptional, (127)
"Everything was great! We really enjoyed the peace and quiet."
The price is HK$942
HK$1,197 total
includes taxes & fees
2 Sept - 3 Sept
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Large Secluded Cabin on the Lake - NOW SLEEPS 10
Fridge, microwave, oven, stovetop

Large Secluded Cabin on the Lake - NOW SLEEPS 10

10.0 out of 10, Exceptional, (58)
"Canin was well stocked, easy to access. Perfect for what we needed. "
Large Secluded Cabin on the Lake - NOW SLEEPS 10
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (60)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is HK$3,164
HK$4,189 total
includes taxes & fees
2 Sept - 3 Sept
Lighthouse Lane
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Property grounds

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
10.0 out of 10, Exceptional, (6)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House
Property grounds

Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

8.8 out of 10, Excellent, (3)
"My husband and his good friend stayed there and absolutely loved everything about the house, location and the host. "
Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House
Charming cabin in the birches right on the atv trail!
Smart TV

Charming cabin in the birches right on the atv trail!

2.0 star property
9.0 out of 10, Wonderful, (6)
"I felt very comfortable. It's a very nice cabin, it has all the amenities, and it's perfect for sharing as a couple or as a family. I had a great time."
The price is HK$1,055
HK$1,558 total
includes taxes & fees
28 Aug - 29 Aug
Charming cabin in the birches right on the atv trail!
Private Dock on Messalonskee Lake: Cozy Cottage!
TV, fireplace, books

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.0 out of 10, Wonderful, (6)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!
Cabin China Lake
Exterior

Cabin China Lake

9.6 out of 10, Exceptional, (13)
"Second time there and is always nice. "
Cabin China Lake
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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Top Oakland Hotel Reviews

The Elmwood

The Elmwood

10/10 Excellent
"Surprisingly quiet considering closeness to freeway and vehicles right outside the door. Unfortunately the Irving lights from behind were shining in through the bathroom window at night and then the sun in the morning. Great friendly staff, Amanda checked us in. There was another lady in the morning shift when I grabbed my mom’s coffee. Spacious and well organized. "
Tamara Juan 1-night trip
Posted 15 hours ago
The Elmwood

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?

The Modern Maine Retreat: This highly rated holiday home rental in Oakland offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable 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 Belgrade Lake house with Dock! as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 29 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.