Hillside Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Hillside

Our top choices for Hillside holiday rentals

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

10.0 out of 10, Exceptional, (310)
"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, (7)
"Phenomenal property with everything and more. Amy was a gracious host, easy to communicate with, and had a robust binder full of information and recommendation that makes weekend planning a breeze. The home was spacious and clean with all the amenities one could ask for. The outdoor space is truly a stunning 180 degree view of beautiful Sebago. We enjoyed hanging out on the dock and playing lawn games and renting pontoons to check out Frye island and the sandbar. Truly a unique home and...
Private Lakefront Estate with 180 Degree Views

Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!

10.0 out of 10, Exceptional, (66)
"Great stay!"
Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!

Sebago Lake Cottage on Raymond Cape

10.0 out of 10, Exceptional, (47)
"Our family was up for a wedding so we came up to visit. This is a beautiful place. We will keep this in mind for the future. "
Sebago Lake Cottage on Raymond Cape

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (60)
"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 NZ$951
includes taxes & fees
24 Sept - 25 Sept
Lakefront Log Home 12 feet Away from Lake

Grand Blanc Mountain Home

9.6 out of 10, Exceptional, (98)
"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

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

Beautiful 6 bedroom cabin on 1100 acre lake in Fryeburg Maine

9.8 out of 10, Exceptional, (14)
"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

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

Ava Jade yurt nestled in the woods of Brownfield, Maine

10.0 out of 10, Exceptional, (13)
"The ava jade yurt was a great spot to unwind. It had everything we needed, was clean, and very comfy in the winter weather. Communication was good and the check-in and check-out processes were easy. "
The price is NZ$279
includes taxes & fees
23 Oct - 24 Oct
Ava Jade yurt nestled in the woods of Brownfield, Maine

The Ski Hive Trailside At Pleasant Mnt

2.0 star property
9.0 out of 10, Wonderful, (4)
"Our heart warming family reunion was a very successful event in this very accommodating and special home. The abundance of nature, peaceful setting, and availability of outdoor activities nearby, makes this Ski Hive special even in the summer. The Braciskas are great hosts."
The Ski Hive Trailside At Pleasant Mnt

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

9.8 out of 10, Exceptional, (167)
"We had a wonderful stay in pauls home. I Highly recommend staying here, its really quiet and peaceful. The home is beautiful inside and out."
The price is NZ$889
includes taxes & fees
5 Oct - 6 Oct
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (47)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery

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

10.0 out of 10, Exceptional, (34)
"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!

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

8.6 out of 10, Excellent, (21)
"Beautiful view, easy access for boating, a great location! The house is small but the 2 levels allowed us to fit 4 family members comfortably. Will plan to visit again!"
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

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

9.6 out of 10, Exceptional, (57)
"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.

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.

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

10.0 out of 10, Exceptional, (13)
"We had the best time ever at this property. Swimming, fishing, dinners on the deck at Sunset PRICELESS!!!"
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

The Flying Mermaid - A cute and cozy lake view cottage just steps to Sebago Lake

10.0 out of 10, Exceptional, (3)
"Great time Thank You"
The Flying Mermaid - A cute and cozy lake view cottage just steps to Sebago Lake

4 Bedroom Lake House with Sandy Entrance & Boat Dock

9.6 out of 10, Exceptional, (15)
"Nice property with ammenities provided. We enjoyed our stay."
The price is NZ$1,232
includes taxes & fees
1 Oct - 2 Oct
4 Bedroom Lake House with Sandy Entrance & Boat 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillside Hotel Reviews

Find out more about Hillside

Find out more about Hillside

Everything you need to know about Hillside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillside holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillside holiday rentals we have selected for you start as low as NZ$279 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 holiday 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 holiday.

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 holiday rentals in Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay.

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

Private Lakefront Estate with 180 Degree Views: This holiday home rental outside of Hillside offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 wider area, you’ll find Sebago Cove and Brandy Pond.

What’s a holiday rental in Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillside. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.