Hillside Vacation Rentals

    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

This weekend
Next weekend

Vacation Rentals in Hillside

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

9.6 out of 10, Exceptional, (85)
"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

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

8.0 out of 10, Very good, (11)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.4 out of 10, Exceptional, (3)
"Cute cabin. Liked the hit tub and quiet area. Kids liked taking the canoe out on the lake. "
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

10.0 out of 10, Exceptional, (9)
"Good location, good fishing"
Professionally styled waterfront cottage on Sebago. Cozy and Serene.

Stand alone waterfront rustic cabin!

10.0 out of 10, Exceptional, (46)
"Beautiful property, nice and quiet"
Stand alone waterfront rustic cabin!

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

9.4 out of 10, Exceptional, (13)
"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

Waterfront Maine cottage! Next to Sebago Lake State Park!

9.8 out of 10, Exceptional, (20)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (50)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake

Three-story Canadian Lighthouse

9.8 out of 10, Exceptional, (53)
"Communication with Host was thorough, prompt and very helpful. We thoroughly enjoyed our stay. Property was spotless and well stocked with not only necessities, but plenty of extra comforts. We hope to visit again soon."
Three-story Canadian Lighthouse

Great Place for a Family Retreat! Sleeps 10

9.6 out of 10, Exceptional, (11)
"Nice clean property close to everything."
Great Place for a Family Retreat! Sleeps 10

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

9.8 out of 10, Exceptional, (164)
"I stayed here with my girlfriend. We both loved how beautiful the house was and the scenic property. There are wonderful amenities and activities for entertainment. The hot tub was a great feature! Overall the house was perfect, very clean, the bed was so comfortable and the game area downstairs made it a fun stay! Would recommend this to anyone who is looking for a peaceful, fun retreat! "
The price is CA $307
CA $635 total
includes taxes & fees
Aug 6 - Aug 7
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

Secluded Cabin on 400 Acres: Swim, Hike, Fish, Relax, PLAY!

10.0 out of 10, Exceptional, (113)
"Loved it"
Secluded Cabin on 400 Acres: Swim, Hike, Fish, Relax, PLAY!

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

9.8 out of 10, Exceptional, (118)
"My family and I had a wonderful stay. The cabin is great, the location is beautiful and so peaceful and Kyle is a wonderful host. I would definitely want to stay there again on my next trip to Maine."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (57)
"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 $981
CA $1,349 total
includes taxes & fees
Jul 28 - Jul 29
Lakefront Log Home 12 feet Away from Lake

Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

2.0 out of 10, (1)
Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

2.0 star property
8.0 out of 10, Very good, (2)
"Great place! Loved it"
Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

Lakefront camp with cozy cottage-style interior and board games - kayaks welcome

9.6 out of 10, Exceptional, (15)
"Nice place and was perfect for our needs."
Lakefront camp with cozy cottage-style interior and board games - kayaks welcome

Maine Lakefront Cottage Rental with Sandy Beach

9.2 out of 10, Wonderful, (40)
"Loved the lake and location. Planning on stay again."
Maine Lakefront Cottage Rental with Sandy Beach

Million-Dollar View: Waterfront Cabin in Bridgton!

Million-Dollar View: Waterfront Cabin in Bridgton!

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

10.0 out of 10, Exceptional, (303)
"Place is beautiful and well crafted with a perfect nature setting"
Romantic getaway for 2 couple date's in July just opened up
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

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?

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]: This vacation home near Hillside is located in a rural location and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Hillside?

Choose from 350 Expedia vacation rentals in Hillside for a memorable vacation.

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 Brandy Pond and Sebago Lake State Park.

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.