Hillside Vacation Rentals

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Our top choices for Hillside vacation rentals

Nature Lover's Paradise!

Nature Lover's Paradise!
Fryeburg
9.8 out of 10, Exceptional, (56)
"We enjoyed our stay. The house was clean and stocked with everything you need. "
United States
Karin S.
Nature Lover's Paradise!

Lakefront Log Home 12 feet Away from Lake

Lakefront Log Home 12 feet Away from Lake
Bridgton
10.0 out of 10, Exceptional, (63)
"great commication and amazing cabin "
United States
Matthew A.
$511 nightly
The price is $557
Dec 14 - Dec 15
Total with taxes and fees
Lakefront Log Home 12 feet Away from Lake

Grand Blanc Mountain Home

Grand Blanc Mountain Home
Eaton
9.6 out of 10, Exceptional, (99)
"Overall fantastic property! the view from the porch was incredible and the house was beautiful. Sadly Wi-Fi was out all weekend but didn't mind being unplugged. "
United States
Charles W.
Grand Blanc Mountain Home

Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views
Raymond
10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views

Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape
Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape

THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (7)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
THE LILLIPAD.Off-grid A frame. Sebago lake region!

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

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
Poland
9.8 out of 10, Exceptional, (15)
"Great location on Thompson lake! Nice dock and swim platform plus sandy beach area. "
United States
Julie W.
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
North Sebago
9.8 out of 10, Exceptional, (84)
"Wonderful stay at the camp. Very clean and looked exactly like the pictures. Super close to Nason’s beach. Highly recommend this property. "
United States
Kerry M.
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

Romantic getaway for 2 PEAK fall foliage!!!

Romantic getaway for 2 PEAK fall foliage!!!
Naples
10.0 out of 10, Exceptional, (313)
"Perfect waterfront property. Not far from all the action in town. Has all the needed amenities to make this a memorable vacation we won't forget. "
United States
Owen E.
Romantic getaway for 2 PEAK fall foliage!!!

WATERFRONT ON LONG LAKE

WATERFRONT ON LONG LAKE
HARRISON
9.8 out of 10, Exceptional, (10)
"Great place, everything was clean. There is a ton of room, the place is bigger in person. Overall it was a great place for the weekend."
United States
David D.
WATERFRONT ON LONG LAKE

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Bridgton
10.0 out of 10, Exceptional, (18)
"Stay was great, as advertised."
United States
Mary Campbell K.
$157 nightly
The price is $171
Dec 14 - Dec 15
Total with taxes and fees
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Three-story Canadian Lighthouse

Three-story Canadian Lighthouse
Fryeburg
9.8 out of 10, Exceptional, (64)
"Great stay"
United States
pam l.
Three-story Canadian Lighthouse

Serenity - Stunning Sebago Lake scenery

Serenity - Stunning Sebago Lake scenery
Casco
10.0 out of 10, Exceptional, (50)
"Beautiful and clean, all the amenities!!! "
United States
tina b.
Serenity - Stunning Sebago Lake scenery

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

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Conway
9.8 out of 10, Exceptional, (172)
"Great place, location."
United States
Jonathan N.
$583 nightly
The price is $633
Dec 18 - Dec 19
Total with taxes and fees
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

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

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C
Standish
8.6 out of 10, Excellent, (21)
"Beautiful cabin in a super scenic location, clean and cozy and the air conditioning was a huge plus for the hot days"
United States
Amelia E.
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

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

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Gray
9.4 out of 10, Exceptional, (92)
"Wonderful place to getaway "
United States
David A.
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

Condo at Pleasant Mountain

Condo at Pleasant Mountain
Bridgton
9.8 out of 10, Exceptional, (21)
"Great place to stay! Quiet and comfortable, very clean. The host was very helpful."
United States
Christiane S.
Condo at Pleasant Mountain

Njoy Luxury - MUST experience this exclusive and stunning lakeview home

Njoy Luxury - MUST experience this exclusive and stunning lakeview home
Bridgton
9.6 out of 10, Exceptional, (18)
"Wonderful house for an extended family gathering. Gourmet kitchen allowed us the make delectable meals together. Outdoor patio is lovely. Beds are very comfortable. Air conditioning works well. Would definitely return."
United States
Sally D.
Njoy Luxury - MUST experience this exclusive and stunning lakeview home

Beautiful home with 150ft sandy beach and private boat launch on Big Sebago!!!!!

Beautiful home with 150ft sandy beach and private boat launch on Big Sebago!!!!!
Raymond
10.0 out of 10, Exceptional, (12)
"Nice place right near the marina "
United States
zachary p.
Beautiful home with 150ft sandy beach and private boat launch on Big Sebago!!!!!

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

Professionally styled waterfront cottage on Sebago. Cozy and Serene.
North Sebago
10.0 out of 10, Exceptional, (21)
"Lovely home in a beautiful location!"
United States
Jennifer H.
Professionally styled waterfront cottage on Sebago. Cozy and Serene.
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

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $171 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Grand Blanc Mountain Home: This vacation home rental near Hillside is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 Lake State Park and Long Lake.

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.