Photo by Marc Maheu

Holiday Rentals in Oakland

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Holiday Rentals in Oakland

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

9.2 out of 10, Wonderful, (19)
"Location is beautiful and private"
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock

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

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"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

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

9.6 out of 10, Exceptional, (10)
"House was spacious and had all the necessities. The location was nice. Good for a relaxing trip near the water "
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

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

9.6 out of 10, Exceptional, (49)
"Ideal for kayaking and fishing. Beautiful spot."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (34)
"Had a great stay over Xmas holiday seeing the family. ) "
The price is €212
includes taxes & fees
21 May - 22 May
Central Maine Apartment offering 4 Seasons of Fun.

The Cabin Skowhegan

9.8 out of 10, Exceptional, (39)
"The location was great! Close enough to town to be convenient and far enough out to have a remote country feeling. We most likely will return. The cabin was rustic, which had it's charm."
The price is €168
includes taxes & fees
7 May - 8 May
The Cabin Skowhegan

Downtown! Views! Dining! King & Queen beds!

2.0 star property
10.0 out of 10, Exceptional, (9)
"My daughter and I came to Maine for my birthday. The VRBO rental located on Water Street was flawless and exceeded our expectations. Beautifully appointed, Spotlessly clean, cozy and wonderful beds, bedding and pillows. Fun being right on the main street and walkable to most everything. The hosts were so accommodating, wish they had places all over the world. One recommendation is a tv on the kitchen level, I like tv. But the tv area upstairs is simply wonderful, so cozy. Views are delightful...
Downtown! Views! Dining! King & Queen beds!

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

9.4 out of 10, Exceptional, (123)
"Everything was great! We really enjoyed the peace and quiet."
The price is €133
includes taxes & fees
14 May - 15 May
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (36)
"Really enjoyed our stay, will come back. "
The price is €267
includes taxes & fees
7 May - 8 May
April Special, Lake Great Pond, Dog Friendly

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (30)
"Great property!!"
The price is €299
includes taxes & fees
7 May - 8 May
Lakefront, Stunning Home only 30 min to Sugarloaf!

"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations

9.6 out of 10, Exceptional, (56)
"Great location. fishing was awesome!! Tiffany was so nice and accommodating We had a nice few days! very nice getaway!"
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations

Summer Getaway on North Pond - Hidden Harlow Lane Retreat

9.6 out of 10, Exceptional, (25)
"Beautiful property and very nice host"
Summer Getaway on North Pond - Hidden Harlow Lane Retreat

Large New Lakeside Cottage Central Air

8.2 out of 10, Very good, (30)
"Classic Maine lake property - great as a home base for lake activities. House held our 8 people nicely and was as advertised with a responsive host."
Large New Lakeside Cottage Central Air

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious Newer Modern Home

8.0 out of 10, Very good, (38)
"Wish we could've stayed longer. It was a beautiful cabin."
Spacious Newer Modern Home

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (33)
"location was great, the lake and the wildlife were amazing. enjoyed sitting in the glassed in room each night listening to all of the sounds. the kids were a bit shocked by the 'don't drink the water' warnings, which caused a bit of drama, but otherwise, it was a much needed week away."
Every window has a spectacular lake view Low fees

Dog Friendly Cabin Right On The Water!!!

2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!

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

9.8 out of 10, Exceptional, (18)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
The price is €483
includes taxes & fees
3 Jun - 4 Jun
Spacious Country Home w/ Hot Tub, near Colby/Thomas
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, (13)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock

Pressey House Lakeside Bed & Breakfast

3.0 star property
The price is €233
includes taxes & fees
5 Jun - 6 Jun
Pressey House Lakeside Bed & Breakfast

Historic 1840’s Farmhouse Duplex with Modern Comfort – Pets Welcome

Historic 1840’s Farmhouse Duplex with Modern Comfort – Pets Welcome
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. Some other top choices in Oakland are Lakefront Maine House ~ 4 Mi to Colby College and The Modern Maine Retreat.

How many holiday rentals will I find in Oakland?

Choose from 25 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 Samantha Smith, 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.