Hillside Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Hillside holiday rentals

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

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

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (29 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
The price is NZ$363
includes taxes & fees
15 Nov - 16 Nov
Barn on Pleasant-walk to Highland beach & town
A wooden deck with a checkered mat, two wooden chairs, and a table.

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

Relaxing A-Frame with Hot Tub and Lake Access
Denmark
10.0 out of 10, Exceptional, (5 reviews)
"Great house, we had a wonderful time!"
United States
Alex F.
The price is NZ$809
includes taxes & fees
16 Nov - 17 Nov
Relaxing A-Frame with Hot Tub and Lake Access
A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

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

Peaceful Barn Loft near Sebago Lake and Conway, NH
Hiram
The price is NZ$347
includes taxes & fees
25 Nov - 26 Nov
Peaceful Barn Loft near Sebago Lake and Conway, NH
Room

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

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.2 out of 10, Wonderful, (5 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is NZ$264
includes taxes & fees
14 Nov - 15 Nov
Manor Suite,cozy newly renovated,downtown & beach
A wooden cabin with a balcony, stairs leading to the entrance, and string lights.

5. All Points’ End (HOUSE)

All Points’ End (HOUSE)
Naples
The price is NZ$624
includes taxes & fees
2 Dec - 3 Dec
All Points’ End (HOUSE)
A cozy interior of a yurt with a central wood-burning stove, a sofa, and a bed with floral bedding.

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

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (25 reviews)
"Great camping experience"
United States
Kathleen
The price is NZ$265
includes taxes & fees
23 Nov - 24 Nov
Ava Jade yurt nestled in the woods of Brownfield, Maine
A lakeside house with a dock, a small boathouse, and a flag.

7. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveller
The price is NZ$554
includes taxes & fees
1 Dec - 2 Dec
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A lake with a sandy beach and trees on the left.

8. Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (67 reviews)
"This was our second stay at Windsor Cottage, and it was just as wonderful as the first! The cottage is always spotless, beautifully furnished, and truly feels like a home away from home. We love the lake access, the pet-friendly accommodations, and being just minutes from downtown Bridgton. We can’t wait to come back again!"
United States
Cortney C.
The price is NZ$647
includes taxes & fees
16 Nov - 17 Nov
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
A cozy room with a wood-burning stove, a red chair, and a leather ottoman.

9. Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (20 reviews)
"We enjoyed our stay very much!"
United States
Sandy D.
The price is NZ$306
includes taxes & fees
15 Nov - 16 Nov
Rufus III Yurt on the river
A campsite with two blue chairs, a hammock, and a black backpack on the ground.

10. Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods
Brownfield
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful property! Comfortable and clean lodging. "
United States
Ian M.
The price is NZ$298
includes taxes & fees
19 Nov - 20 Nov
Allie Mae Yurt nestled in the woods
A hot tub with a wooden bench in a backyard with a stone wall and trees.

11. Casco Tiny house, and HOT TUB!

Casco Tiny house, and HOT TUB!
Casco
The price is NZ$517
includes taxes & fees
16 Nov - 17 Nov
Casco Tiny house, and HOT TUB!
A living room with a sofa, a coffee table, and a rug. There is a washing machine and a kitchen in the background.

12. The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi

The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi
Bridgton
10.0 out of 10, Exceptional, (3 reviews)
"Host was amazing. Great spot in Bridgton!"
Canada
Joshua
The price is NZ$674
includes taxes & fees
23 Nov - 24 Nov
The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi
A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

13. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
10.0 out of 10, Exceptional, (1 review)
"Nice, clean, good location.Would Recommend!"
United States
glen l.
The price is NZ$783
includes taxes & fees
16 Nov - 17 Nov
Cozy Family Home w/ Beach Access
A multi-story house with a dock and a children's play area.

14. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (19 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is NZ$1,274
includes taxes & fees
22 Nov - 23 Nov
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
A hallway with wooden beams, a hanging clothes rack, a stone-tiled floor, and a door leading to another room.

15. Cozy 1-bedroom cottage in soothing Standish with AC

Cozy 1-bedroom cottage in soothing Standish with AC
Standish
10.0 out of 10, Exceptional, (4 reviews)
"Amazing property & so many things to do around the area, we will definitely try to come back!!"
United States
Alyssa
The price is NZ$509
includes taxes & fees
29 Nov - 30 Nov
Cozy 1-bedroom cottage in soothing Standish with AC
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

16. 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, (16 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is NZ$486
includes taxes & fees
22 Nov - 23 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A cabin by a lake surrounded by trees.

17. Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn

Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn
Bridgton
10.0 out of 10, Exceptional, (73 reviews)
"Cabin is thoughtfully furnished and equipped.We enjoyed listening to the bird song in the mornings, while sitting on the dock."
United States
Peggy P.
The price is NZ$994
includes taxes & fees
23 Nov - 24 Nov
Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn
A modern cabin with a deck, large windows, and a view of the surrounding forest.

18. Waterfront Eco Friendly House Near White Mountains, fire pit, outdoor sauna

Waterfront Eco Friendly House Near White Mountains, fire pit, outdoor sauna
Sweden
10.0 out of 10, Exceptional, (22 reviews)
"We had a lovely and restful stay!"
United States
Anna B.
The price is NZ$725
includes taxes & fees
22 Nov - 23 Nov
Waterfront Eco Friendly House Near White Mountains, fire pit, outdoor sauna
An outdoor patio area with a wooden deck, a barbecue grill, and a seating arrangement.

19. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is NZ$508
includes taxes & fees
22 Nov - 23 Nov
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

20. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is NZ$466
includes taxes & fees
22 Nov - 23 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake
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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Find holiday rentals that suit your style

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Top Hillside Hotel Reviews

A covered outdoor seating area with white wicker chairs and a table, overlooking a forested area.
Noble House Inn

Noble House Inn

Noble House Inn
Bridgton

10/10 Excellent

Noble House Inn in Bridgton Maine was wonderful. Cindi was a fantastic welcoming host. Bridgton is a very quaint town to explore. It was very peaceful- great for relaxing.
Australia
Renee
Reviewed September 22, 2017
Noble House Inn

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$264 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.