Hillside Vacation Rentals

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Vacation Rentals in Hillside

Our top choices for Hillside vacation rentals

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

10.0 out of 10, Exceptional, (309)
"Place is beautiful and well crafted with a perfect nature setting"
Romantic getaway for 2 couple date's in July just opened up

Private Lakefront Estate with 180 Degree Views

10.0 out of 10, Exceptional, (6)
Private Lakefront Estate with 180 Degree Views

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

9.8 out of 10, Exceptional, (87)
"The house was amazing. Perfect amount of things to do and places to just relax. Sebago is a beautiful lake for swimming, boating, or just relaxing. "
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (59)
"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 CA $522
CA $769 total
includes taxes & fees
Sep 11 - Sep 12
Lakefront Log Home 12 feet Away from Lake

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (46)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery

Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine

9.8 out of 10, Exceptional, (12)
"The house was perfect. We had a lovely time and will return."
Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine

4 Bedroom Lake House with Sandy Entrance & Boat Dock

9.6 out of 10, Exceptional, (14)
"Outstanding weekend of fishing and catching up with close friends."
The price is CA $483
CA $996 total
includes taxes & fees
Oct 1 - Oct 2
4 Bedroom Lake House with Sandy Entrance & Boat Dock

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

10.0 out of 10, Exceptional, (16)
"Good location, good fishing"
Professionally styled waterfront cottage on Sebago. Cozy and Serene.

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

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

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

7.8 out of 10, Good, (14)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Great Place for a Family Retreat! Sleeps 10

9.6 out of 10, Exceptional, (13)
"Quiet neighborhood, close to beach and activities. "
Great Place for a Family Retreat! Sleeps 10

Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

10.0 out of 10, Exceptional, (33)
"Sindi and Doug were excellent hosts! The property was extremely clean, welcoming and full stocked with everything needed for a ski weekend!"
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

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

9.4 out of 10, Exceptional, (88)
"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

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

Sunny Waterfront Family Friendly Little Sebago Home

10.0 out of 10, Exceptional, (73)
"Great property and great hosts for a vacation stay. "
Sunny Waterfront Family Friendly Little Sebago Home

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

9.4 out of 10, Exceptional, (6)
"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!

Stand alone waterfront rustic cabin!

10.0 out of 10, Exceptional, (50)
"Beautiful property, nice and quiet"
Stand alone waterfront rustic cabin!

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!

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

10.0 out of 10, Exceptional, (11)
"We loved the house. It was very clean and the view was incredible! Can’t wait to go back!"
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
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

Find out more about Hillside

Find out more about Hillside

Everything you need to know about Hillside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillside vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillside vacation rentals we have selected for you start as low as CA $483 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.