Hillside Holiday Rentals from €170: Search Short-Term Rentals

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Our top choices for Hillside holiday rentals

1. Manor Suite,cozy newly renovated,downtown & beach

Bridgton

Jennifer

includes taxes & fees

26 Oct - 27 Oct

A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

2. Peaceful Barn Loft near Sebago Lake and Conway, NH

Hiram

includes taxes & fees

25 Oct - 26 Oct

A cozy interior of a yurt with a wooden sofa, a wooden chair, and a blue mat on the floor.

3. Ava Jade yurt nestled in the woods of Brownfield, Maine

Brownfield

Kathleen

includes taxes & fees

25 Oct - 26 Oct

A wooden deck with a checkered mat, two wooden chairs, and a table.

4. Relaxing A-Frame with Hot Tub and Lake Access

Denmark

Alex F.

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a stone fireplace, a large bed, a TV, and a wooden floor.

5. Barn on Pleasant-walk to Highland beach & town

Bridgton

Robyn N.

includes taxes & fees

26 Oct - 27 Oct

A rustic room with a wooden ceiling, a hot tub, a black leather chair, and a small table with a flag.

6. Ell Suite walk to town beach

Bridgton

mark l.

includes taxes & fees

1 Nov - 2 Nov

A circular skylight with a wooden frame and a view of trees through the sky.

7. Allie Mae Yurt nestled in the woods

Brownfield

Ian M.

includes taxes & fees

23 Oct - 24 Oct

A cozy room with a wood-burning stove, a red chair, and a leather ottoman.

8. Rufus III Yurt on the river

Brownfield

Sandy D.

includes taxes & fees

23 Oct - 24 Oct

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Top Hillside Hotel Reviews

Oxford Casino Hotel

10/10 Excellent

"room was clean and staff was friendly"

Center Lovell Inn

8/10 Good

"We spent 2 nights here during our leaf peeping fall road trip. The inn is 200 years old and so quaint. Our host was lovely. Our room was spotless. The bed was a bit too firm for our liking. I did mark down my rating for the amenities simply because there was no coffee in the room or in the lobby. Other that that, our stay was very nice and I would stay here again and would recommend the inn to my friends. The view was beautiful! T&J Smith"

Cozy cabin near Conway Lake and North Conway

10/10 Excellent

"The cabin was as described. Added bonus, the floor in the downstairs bathroom is heated which was amazing for those chilly nights/mornings we had. There are plenty of household items available for use. If we would have needed something, it is sure to have already been there. We were in town for a wedding and it fit five of us perfectly! Perfect location between North Conway and Fryeburg, Maine."

The Poland Spring Resort

10/10 Excellent

"This historic property with 30+ buildings covering 500+ acres is a lovely setting year round. Rooms have some age on them but are comfortable. Staff was very friendly. Buffet breakfast was good. On a clear day New Hampshire’s White Mountains are visible from the Inn and golf course. The museum is amazing. There was walking trails, pickleball and tennis courts,…we stayed there twice on our trip. The first time, we picked up friends at the airport in Portland, spent the night here, then headed to the White Mountains of NH in the morning. Later on our foliage journey, we spent two more nights and did day trips from here. (Including the nearby Shaker Collage Fall Festival)."

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, apart-hotels, 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 €170 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?

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room: This holiday home rental outside of Hillside is located in the city centre, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Brandy Pond and Sebago Lake State Park.

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.

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Check prices for these dates

Our top choices for Hillside holiday rentals

1. Manor Suite,cozy newly renovated,downtown & beach

2. Peaceful Barn Loft near Sebago Lake and Conway, NH

3. Ava Jade yurt nestled in the woods of Brownfield, Maine

4. Relaxing A-Frame with Hot Tub and Lake Access