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Oakland Holiday Rentals

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Holiday Rentals in Oakland

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

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

8.6 out of 10, Excellent, (14)
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. The neighbors on the cove still had lots of water toys set up. When we called, we were told that they put the Paddleboards and kayaks away October 1st. There was no mention of that in the listing and...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
Miscellaneous

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (32)
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything! "
The price is AU$393
includes taxes & fees
26 Dec - 27 Dec
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond Cottage: private mooring & shared dock
Miscellaneous

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (8)
"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
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Miscellaneous

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

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
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, (124)
"Cabin was amazing. My second time staying at this place. Amazing host. Clean cabin with all the amendities. "
The price is AU$204
includes taxes & fees
1 Dec - 2 Dec
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (36)
"Larry hosted us for a week with our dogs while we were on a house-hunting expedition. Larry was a perfect host; very attentive but allowed us our space. The Cabin is very cozy and while there is no kitchen sink, the property details disclose this so we were prepared. It was a wonderful stay!"
The price is AU$290
includes taxes & fees
1 Dec - 2 Dec
The Cabin Skowhegan
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, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
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, (110)
"We come to this cabin twice a year and always love it! Spring summer and fall are beautiful months to be on clearwater pond. The perfect getaway! "
Private three season cabin nestled in woods on shore of pristine Maine lake
Every window has a spectacular lake view Low fees
Miscellaneous

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (31)
"We chose this property based on it's proximity to relatives we were visiting, the low fees (like you, I refuse to pay a $300 'host fee'), the reports of a easy-to-communicate with property manager and views from every window. We were NOT disappointed. I especially want to thank Tina for her fast responses to any questions, and her flexibility and generosity. Due to the time of year, we were unable to enjoy the swimming and boating so many others rave about. But we did enjoy sitting in the...
Every window has a spectacular lake view Low fees
The Cabbage on Olive Street, overlooking Hayden Brook
Property grounds

The Cabbage on Olive Street, overlooking Hayden Brook

9.0 out of 10, Wonderful, (11)
"If you, dear reader, and I have anything in common, then you're reading this at 1am after a long work day and you've reached this listing by googling "places to stay in Maine under $100." You're also probably saying to yourself "What a quaint little cabin in the heart of Stephen King country! I wonder if anything Stephen King-related would happen to me if I stayed there?" Dear reader, let me put your fears to rest: book the dang cabin!!! I went here on my first solo vacation and could not have...
The Cabbage on Olive Street, overlooking Hayden Brook
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Aerial view

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!
Miscellaneous

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (25)
"Great property!!"
Lakefront, Stunning Home only 30 min to Sugarloaf!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards
Property grounds

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

9.8 out of 10, Exceptional, (24)
"Roxie was a cozy tiny cabin! It was absolutely perfect for the one night passing through with the dog. My only regret was not having more time to make it a longer stay. The cabin has everything you need for a stay! The wood stove did a great job heating it, and it stayed pretty warm all night. GPS took me right there, no issue finding the road. And while no WiFi, cell service was fine and could stream playoff baseball before bed. Would 10/10 stay again and for longer if back in the area! "
The price is AU$246
includes taxes & fees
4 Dec - 5 Dec
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
On the beach, sun-loungers

Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat

9.6 out of 10, Exceptional, (25)
"The view of the lake is beautiful and the loon was perfect, but we did not have drinkable water and for the price of cleaning and using only the Loon it was overpriced for the stay. "
Cozy Winter Getaway on North Pond - Hidden Harlow Lane Retreat
Dog Friendly Cabin Right On The Water!!!
Exterior detail

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!!!
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Property grounds

5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE

10.0 out of 10, Exceptional, (4)
"The house had a lot of room. This would be a great family getaway place. The host was available and very attentive. I would recommend this house. "
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (158)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.
Sunset Chalet- Stylish Waterfront Gem
Dining

Sunset Chalet- Stylish Waterfront Gem

10.0 out of 10, Exceptional, (23)
"We loved the Sunset Chalet! Very comfortable and all of the welcoming goodies & fresh flowers! We enjoyed our short but sweet stay! Beautiful view of the stream surrounded by the best smelling pine trees! The host was wonderful & very welcoming! Cant wait to visit again! sweet stay! "
The price is AU$1,245
includes taxes & fees
1 Dec - 2 Dec
Sunset Chalet- Stylish Waterfront Gem
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
Interior

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

8.6 out of 10, Excellent, (14)
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. The neighbors on the cove still had lots of water toys set up. When we called, we were told that they put the Paddleboards and kayaks away October 1st. There was no mention of that in the listing and...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
Miscellaneous

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (32)
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything! "
The price is AU$393
includes taxes & fees
26 Dec - 27 Dec
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond Cottage: private mooring & shared dock
Miscellaneous

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (8)
"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
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.
Beautiful view of the beach with palm trees

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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 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 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 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.