Hillside Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Hillside holiday rentals

Property grounds
Manor Suite,cozy newly renovated,downtown & beach

Holiday Home in Bridgton

Manor Suite,cozy newly renovated,downtown & beach
10.0 out of 10, Exceptional, (1)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is HK$709
HK$1,324 total
includes taxes & fees
14 Jan - 15 Jan 2026
Manor Suite,cozy newly renovated,downtown & beach
Outdoor dining
Waterfront Access with Kayaks, Private Deck and a Firepit

Cabin in Gray

Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is HK$1,042
HK$5,301 total
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Access with Kayaks, Private Deck and a Firepit
Exterior
Relaxing A-Frame with Hot Tub and Lake Access

Chalet in Denmark

Relaxing A-Frame with Hot Tub and Lake Access
10.0 out of 10, Exceptional, (2)
"Great house, we had a wonderful time!"
United States
Alex F.
Relaxing A-Frame with Hot Tub and Lake Access
Dining
Ava Jade yurt nestled in the woods of Brownfield, Maine

Camping in Brownfield

Ava Jade yurt nestled in the woods of Brownfield, Maine
10.0 out of 10, Exceptional, (17)
"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. "
United States
Sean M.
The price is HK$855
HK$1,271 total
includes taxes & fees
28 Dec - 29 Dec
Ava Jade yurt nestled in the woods of Brownfield, Maine
Fridge, microwave, oven, stovetop
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Cottage in Brownfield

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
10.0 out of 10, Exceptional, (3)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is HK$1,194
HK$2,463 total
includes taxes & fees
6 Jan - 7 Jan 2026
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Exterior
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

Holiday Home in Casco

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!
10.0 out of 10, Exceptional, (14)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is HK$1,275
HK$5,072 total
includes taxes & fees
6 Jan - 7 Jan 2026
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!
2 bedrooms, desk, WiFi, bed sheets
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Aparthotel in Lovell

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
10.0 out of 10, Exceptional, (5)
"Very nice stay. Perfect for a couple of adults. "
United States
Joann M.
The price is HK$855
HK$1,797 total
includes taxes & fees
5 Jan - 6 Jan 2026
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
1 bedroom, desk, free WiFi, bed sheets
Spacious Studio Near Sebago Lake

Apartment in Windham

Spacious Studio Near Sebago Lake
2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is HK$805
HK$1,047 total
includes taxes & fees
30 Dec - 31 Dec
Spacious Studio Near Sebago Lake
Property grounds
Rufus III Yurt on the river

Camping in Brownfield

Rufus III Yurt on the river
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay very much!"
United States
Sandy D.
The price is HK$1,089
HK$1,458 total
includes taxes & fees
28 Dec - 29 Dec
Rufus III Yurt on the river
Terrace/patio
Allie Mae Yurt nestled in the woods

Camping in Brownfield

Allie Mae Yurt nestled in the woods
10.0 out of 10, Exceptional, (21)
"Beautiful property! Comfortable and clean lodging. "
United States
Ian M.
The price is HK$933
HK$1,356 total
includes taxes & fees
28 Dec - 29 Dec
Allie Mae Yurt nestled in the woods
Property grounds
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Condo in Bridgton

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
10.0 out of 10, Exceptional, (18)
"Stay was great, as advertised."
United States
Mary Campbell K.
The price is HK$1,061
HK$1,326 total
includes taxes & fees
30 Dec - 31 Dec
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Outdoor spa tub
Luxe Lodge in the Woods! With Sauna & Hot tub

Holiday Home in Conway

Luxe Lodge in the Woods! With Sauna & Hot tub
10.0 out of 10, Exceptional, (2)
"Beautiful property with everything a family with young kids needs. Especially love the hottub and air hockey table!"
United States
Anonymous traveller
The price is HK$1,695
HK$4,286 total
includes taxes & fees
5 Jan - 6 Jan 2026
Luxe Lodge in the Woods! With Sauna & Hot tub
Exterior
Clean+Modern Cozy A-frame

Holiday Home in Fryeburg

Clean+Modern Cozy A-frame
10.0 out of 10, Exceptional, (13)
"Easy check in, great hosts. Highly recommend!"
United States
Thomas S.
The price is HK$2,296
HK$4,088 total
includes taxes & fees
29 Dec - 30 Dec
Clean+Modern Cozy A-frame
Smart TV, books, stereo
Adventure Tower: Family Fun for All Ages!

Apartment in Conway

Adventure Tower: Family Fun for All Ages!
2.0 star property
9.0 out of 10, Wonderful, (2)
"This was an amazing stay for our family and fur babies, super clean, comfortable, with all of the amenities of home! Very close to all of the mountains, restaurants, downtown yet so very private and quiet.Abbey and the Indigo Team are SO responsive and go over and above to ensure you have everything you need for a comfortable and enjoyable stay.Definitely recommend this special spot and we hope to go back! "
United States
Renee F.
The price is HK$1,348
HK$3,878 total
includes taxes & fees
12 Jan - 13 Jan 2026
Adventure Tower: Family Fun for All Ages!
Smart TV
NEW! Gray Woodland Escape | Golf, Pool & Cinema

Holiday Home in Gray

NEW! Gray Woodland Escape | Golf, Pool & Cinema
10.0 out of 10, Exceptional, (1)
The price is HK$3,685
HK$7,341 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Gray Woodland Escape | Golf, Pool & Cinema
Outdoor spa tub
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

Holiday Home in Conway

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
9.8 out of 10, Exceptional, (172)
"Great place, location."
United States
Jonathan N.
The price is HK$2,099
HK$4,050 total
includes taxes & fees
2 Jan - 3 Jan 2026
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Interior
River Access, hot tub, dogs!

Holiday Home in Conway

River Access, hot tub, dogs!
8.0 out of 10, Very good, (1)
"Process was easy. Location was quiet. The “river access” was across the street and fine for launching a boat, but unsuitable for much else. "
United States
Daniel M.
The price is HK$1,271
HK$3,405 total
includes taxes & fees
12 Jan - 13 Jan 2026
River Access, hot tub, dogs!
Outdoor spa tub
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit

Holiday Home in Sebago

Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
10.0 out of 10, Exceptional, (2)
"The whole stay was perfect from checking in to departure. The pool was great and my 2 granddaughters enjoyed it. The house was very clean and everything stalked fully. Definitely would stay here again."
United States
Michele B.
The price is HK$2,169
HK$3,661 total
includes taxes & fees
2 Jan - 3 Jan 2026
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Terrace/patio
LUX Designer Private Waterfront Crooked River SEBAGO

Holiday Home in Naples

LUX Designer Private Waterfront Crooked River SEBAGO
10.0 out of 10, Exceptional, (3)
"Clean, modern, comfortable and private! Loved it!"
United States
Laurie G.
LUX Designer Private Waterfront Crooked River SEBAGO
Outdoor dining
River’s Ranch

Holiday Home in Naples

River’s Ranch
9.4 out of 10, Exceptional, (3)
"Beautiful house. Would highly recommend. "
United States
Michael R.
The price is HK$2,974
HK$6,115 total
includes taxes & fees
27 Dec - 28 Dec
River’s Ranch
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

Dormir

Dormir

10/10 Excellent
"Yes"
Lynette 1-night trip
Posted 5 days ago
Dormir

Find out more about Hillside

Search for holiday rentals in Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside using one of the methods below:

  • View our selection of featured holiday rentals in Hillside
  • Use the map to find apartments and other holiday homes in the Hillside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillside while they last

Look no further and take a look at our great range of rental properties in Hillside!

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?

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views: This holiday home rental outside of Hillside is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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 Lake State Park and Long Lake.

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.