Photo by Marc Maheu

Holiday Rentals in Oakland

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Holiday Rentals in Oakland

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

9.6 out of 10, Exceptional, (10)
"We spent a beautiful fall weekend at Cedar Estates, the house was clean and very well equipped, as described in the listing. We enjoyed a nice campfire on Saturday night at the fire pit. Our 2 dogs really enjoyed exploring and running outside as well! Clean sheets and towels, hot water - lovely overall!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (11)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock

Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

2.0 star property
10.0 out of 10, Exceptional, (2)
"We were just there for the weekend but if I could have stayed longer I would have . The house was clean and had plenty of space for everyone it was just my husband and me and our two grandkids but we had so much room and we did not even use the one room or the loft . The kitchen had everything you needed and then some I enjoyed the mint tea the owner had left for everyone. . They have soaps, bags,, spices, it all the little touches that make this place special. Can’t wait to go back."
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

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

9.4 out of 10, Exceptional, (11)
"My wife and I are big fans of Maine Cabin Masters, which brought us to Maine for the lake cabin experience. It was exactly what we were looking for and accurately presented on the VRBO site. It was great, even including the ladder up to the loft for bed each night. Extremely good host and good location. We really enjoyed our stay."
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

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

9.6 out of 10, Exceptional, (49)
"It was OK."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

The Modern Maine Retreat

10.0 out of 10, Exceptional, (2)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat

Lakefront Maine House ~ 4 Mi to Colby College

8.0 out of 10, Very good, (2)
"Convenient very clean but we were hardly there except to sleep. Thank you"
Lakefront Maine House ~ 4 Mi to Colby College

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (18)
"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

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (238)
"We loved this place very much. Everything was so easy and the home/location were beautiful. We definitely plan on another trip in the future. "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

March Special, Ice Fishing, Dog Friendly

10.0 out of 10, Exceptional, (30)
"Accurate listing, great location (easy drive to Augusta for dinner), really peaceful and quiet. GPS had a minor problem right at the end trying to send us through a neighbor's trailer, but we figured it out (the external pictures helped). Loved our stay there, even though it was just overnight on the way to somewhere else. Next time, we'll stay for a week."
The price is €286
includes taxes & fees
10 Feb - 11 Feb
March Special, Ice Fishing, Dog Friendly

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 !

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (37)
"A lovely cozy house, well situated close to downtown and easy access to stores. The house was very clean and tidy. Cozy and felt like home, and worked out well for our Thanksgiving break with our college students. Would use againnif dates worked out."
Cozy House in the heart of Waterville Maine.

Lighthouse Lane

10.0 out of 10, Exceptional, (52)
"The house was really nice. Updated with all modern appliances and very clean. The beds were very comfy. The scenery is beautiful on the lake. Wish there was coffee for the morning but wasn’t replaced from the previous tenants. Overall definitely recommend. "
The price is €462
includes taxes & fees
4 Mar - 5 Mar
Lighthouse Lane

Luxurious lakefront home with 750' of spectacular frontage on Great Pond

10.0 out of 10, Exceptional, (3)
"Property was exactly as listed - view of the lake from the deck and living rooms was beautiful. Host was very available and responsive. We had a wonderful time - there were 3 generations of our family with up to 14 members staying at the home. We also hosted a larger family get-together with an additional 10 people for an afternoon with permission from the host. Everyone was impressed with the house, property, lake views, deck and dock. Four of our young adult cousins stayed in the log cabin...
Luxurious lakefront home with 750' of spectacular frontage on Great Pond

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (16)
"The house was great in every way. "
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (26)
"Great property!!"
The price is €324
includes taxes & fees
4 Feb - 5 Feb
Lakefront, Stunning Home only 30 min to Sugarloaf!

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

9.8 out of 10, Exceptional, (81)
"Great property, third tine here, excellent stocked kitchen"
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

9.8 out of 10, Exceptional, (25)
"The cabin was so ingeniously set up with battery packs for lighting and plenty of wood for the stove. It gave it an even cozier feel. The land is beautiful and the lake was amazing to look at especially frozen over. I’m so excited to see what the owners do with the property since they are currently developing it. The lake looked stocked with canoes and there is a cute, sturdy dock and places to sit and admire the water in the warmer months. The host was very communicative and gave us...
The price is €192
includes taxes & fees
4 Feb - 5 Feb
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

Large Secluded Cabin on the Lake - NOW SLEEPS 10

10.0 out of 10, Exceptional, (46)
"Exceptional camp on a secluded pond. The hosts went above and beyond making sure our family had everything we needed for a pleasant stay. Literally everything we could have hoped for in our stay was available on the property. "
Large Secluded Cabin on the Lake - NOW SLEEPS 10

The Cabin Skowhegan

9.8 out of 10, Exceptional, (38)
"In an age of "Live Laugh Love" vacation rentals -- every property a generic flip, done up in neutral tones and mass-manufactured message art -- it was so refreshing to enter the Cabin Skowhegan, where everything seemed like a real live person had put it there. The photos of local sites, sometimes captioned. The worn-in but sturdy and inviting furniture, arranged for comfort. The quirky mug collection, clearly someone's pride and joy, hanging around the dining area. Supplies and provisions...
The Cabin Skowhegan
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

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (11)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

2.0 star property
10.0 out of 10, Exceptional, (3)
"The home is perfectly appointed and Diane has put a lot of thought into making your stay special. The view of the snow covered lake was beautiful. I can only imagine how wonderful it would be in the summer. "
The price is €262
includes taxes & fees
4 Feb - 5 Feb
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

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

9.6 out of 10, Exceptional, (10)
"We spent a beautiful fall weekend at Cedar Estates, the house was clean and very well equipped, as described in the listing. We enjoyed a nice campfire on Saturday night at the fire pit. Our 2 dogs really enjoyed exploring and running outside as well! Clean sheets and towels, hot water - lovely overall!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
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 & shared dock: 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 Maine House ~ 4 Mi to Colby College as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 24 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 First Congregational Church, 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.