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Holiday Rentals in Oakland

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Holiday Rentals in Oakland

The Modern Maine Retreat

8.8 out of 10, Excellent, (8)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (56)
"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

9.0 out of 10, Wonderful, (20)
"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

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 €205
includes taxes & fees
7 Aug - 8 Aug
Sister A-Frame in Woods B

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

9.2 out of 10, Wonderful, (12)
"Such a nice little spot to relax on the lake."
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

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

9.0 out of 10, Wonderful, (22)
"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!

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

9.2 out of 10, Wonderful, (15)
"Great location and wonderful hosts!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

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

Lakefront Oakland Vacation Rental w/ Dock + Views!

9.0 out of 10, Wonderful, (4)
"The rental unit was clean and appropriately furnished, with just the right amount of Maine-style quirkiness regarding layout. It was a convenient location for exploring the nearby surrounding area."
Lakefront Oakland Vacation Rental w/ Dock + Views!

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (16)
"The stay was a very nice place and we will be coming back with the whole family next time. "
Cozy Long Pond Cottage: private mooring & shared dock

Belgrade Lake house with Dock!

Belgrade Lake house with Dock!

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (18)
"Awesome cabin on Dexter Pond! Rick and LouAnne were terrific hosts! We loved drinking coffee on porch overlooking the pond, watching sunset and kayaking. Saw family of loons and bald eagle on the large pond. Classic Maine cabin! Not big but comfortable. Hosts were very responsive if we had any questions. Make sure to try their farm fresh eggs and honey!! Hope to visit again!! "
Escape to our cozy Winthrop cabin on Dexter Pond

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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

8.0 out of 10, Very good, (2)
"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

Every window has a spectacular lake view Low fees

9.8 out of 10, Exceptional, (37)
"We had an amazing time and will definitely book again."
Every window has a spectacular lake view Low fees

Large Secluded Cabin on the Lake - NOW SLEEPS 10

10.0 out of 10, Exceptional, (55)
"Only slept there and very comfortable"
Large Secluded Cabin on the Lake - NOW SLEEPS 10

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.6 out of 10, Excellent, (11)
"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 €303
includes taxes & fees
17 Aug - 18 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (31)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Lighthouse Lane

10.0 out of 10, Exceptional, (57)
"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 €582
includes taxes & fees
5 Aug - 6 Aug
Lighthouse Lane
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

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 27 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.