Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Hillside

Romantic getaway for 2 couple date's in July just opened up
Exterior

Romantic getaway for 2 couple date's in July just opened up

10.0 out of 10, Exceptional, (308)
"Place is beautiful and well crafted with a perfect nature setting"
Romantic getaway for 2 couple date's in July just opened up
Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine
Property grounds

Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine

9.8 out of 10, Exceptional, (12)
"House and lake were beautiful, and there was a floating dock that was a wonderful unexpected surprise."
Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine
Serenity - Stunning Sebago Lake scenery
Interior

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (45)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery
Waterfront Conway Vacation Rental w/ Deck!
TV, fireplace, heated floors

Waterfront Conway Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (36)
"Nice cabin on Conway lake, kids had a blast kayaking and fishing."
Waterfront Conway Vacation Rental w/ Deck!
Lakefront Cottage - private dock, large decks, large fire pit
Property grounds

Lakefront Cottage - private dock, large decks, large fire pit

9.4 out of 10, Exceptional, (24)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
Grand Blanc Mountain Home
Interior

Grand Blanc Mountain Home

9.6 out of 10, Exceptional, (96)
"What a treat to stay in such a magnificent home. Great fun to just look around and appreciate the scale and attention to detail that is everywhere. Great comforts and utility made our stay so enjoyable. Thank you!"
Grand Blanc Mountain Home
Stand alone waterfront rustic cabin!

Stand alone waterfront rustic cabin!

10.0 out of 10, Exceptional, (49)
"Beautiful property, nice and quiet"
Stand alone waterfront rustic cabin!
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Exterior

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

7.8 out of 10, Good, (13)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Lakefront Log Home 12 feet Away from Lake
Exterior

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (58)
"Incredible night away on a quiet Maine pond. Highly recommended, Todd was great and the place was perfect! We will be back for sure."
The price is ￥55,963
￥82,947 total
includes taxes & fees
Sep 9 - Sep 10
Lakefront Log Home 12 feet Away from Lake
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Outdoor spa tub

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

9.8 out of 10, Exceptional, (167)
"The property owner greeted us and gave us a thorough walk thru of the property. He was very kind. The property was amazing and we had a very relaxing stay."
The price is ￥39,974
￥77,105 total
includes taxes & fees
Sep 7 - Sep 8
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Great Place for a Family Retreat! Sleeps 10
Outdoor dining

Great Place for a Family Retreat! Sleeps 10

9.6 out of 10, Exceptional, (13)
"Nice clean property close to everything."
Great Place for a Family Retreat! Sleeps 10
Outstanding Pet Friendly Family Retreat on Frye Island in Sebago Lake sleeps 7
Smart TV, fireplace, DVD player, books

Outstanding Pet Friendly Family Retreat on Frye Island in Sebago Lake sleeps 7

9.6 out of 10, Exceptional, (56)
"Hosts were so accommodating location was perfect just a few hiccups will be back again next year exact dates tbd"
Outstanding Pet Friendly Family Retreat on Frye Island in Sebago Lake sleeps 7
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.
Outdoor dining

Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.

9.8 out of 10, Exceptional, (87)
"Family reunion "
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (87)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Condo at Pleasant Mountain
Fridge, microwave, oven, stovetop

Condo at Pleasant Mountain

9.8 out of 10, Exceptional, (20)
"Loved this property, will book again."
Condo at Pleasant Mountain
Yacht Life
Interior

Yacht Life

9.6 out of 10, Exceptional, (4)
"Stating on a boat was a good experience "
Yacht Life
Sunny Waterfront Family Friendly Little Sebago Home
Miscellaneous

Sunny Waterfront Family Friendly Little Sebago Home

10.0 out of 10, Exceptional, (72)
"Great property and great hosts for a vacation stay. "
Sunny Waterfront Family Friendly Little Sebago Home
Glamorous cottage-glamping at Sebago Lake
Terrace/patio

Glamorous cottage-glamping at Sebago Lake

9.8 out of 10, Exceptional, (77)
"We had an amazing time at Bo and Frank’s and would love to come back in the future!"
Glamorous cottage-glamping at Sebago Lake
The Lookout on Pettingill Pond - waterfront house, 5 min from Sebago Lake!
Dining

The Lookout on Pettingill Pond - waterfront house, 5 min from Sebago Lake!

9.6 out of 10, Exceptional, (5)
"The house was beautiful and the lake is gorgeous. The morning views of the sun on the lake were stunning. The house was very clean and well stocked. We were a bit disappointed that the hot tub was a little run down, and there were swarms of insects under the cover so we couldn’t go in. But the pool table and game machine made up for it. Glenn was very communicative. A storm knocked out our power for a bit and caused some water pooling in the basement. Glenn was reachable immediately and...
The Lookout on Pettingill Pond - waterfront house, 5 min from Sebago Lake!
Waterfront Maine cottage! Next to Sebago Lake State Park!
Marina

Waterfront Maine cottage! Next to Sebago Lake State Park!

9.4 out of 10, Exceptional, (28)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!
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 Hillside Hotel Reviews

Admiral Peary Inn

Admiral Peary Inn

10/10 Excellent
"The staff was customer friendly."
Mariah 1-night trip
Posted 1 month ago
Admiral Peary Inn

Find out more about Hillside

Find out more about Hillside

Search for holiday rentals in Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Hillside?

Yes, we give you a choice of vacation rentals close to top sights in Hillside, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Hillside has to offer?

Serenity - Stunning Sebago Lake scenery: This vacation home rental near Hillside is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Hillside?

Wards Cove and Peabody Pond are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Sebago Cove and Brandy Pond.

What’s a vacation rental in Hillside like?

Vacation rentals are private properties you can stay in for a long or short time in Hillside. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.