Hillside Vacation Rentals

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Check prices for these dates

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

Our top choices for Hillside vacation rentals

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

Vacation 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 ￥13,970
￥26,343 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Manor Suite,cozy newly renovated,downtown & beach
Fridge, microwave, oven, stovetop
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 traveler
The price is ￥24,823
￥111,081 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Waterfront Access with Kayaks, Private Deck and a Firepit
Terrace/patio
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
Interior
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 ￥17,173
￥25,525 total
includes taxes & fees
Dec 28 - Dec 29
Ava Jade yurt nestled in the woods of Brownfield, Maine
Exterior
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 ￥23,980
￥49,451 total
includes taxes & fees
Jan 7 - Jan 8, 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!

Vacation 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 ￥25,732
￥102,003 total
includes taxes & fees
Jan 12 - Jan 13, 2026
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!
Living area
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 ￥17,259
￥36,256 total
includes taxes & fees
Jan 5 - Jan 6, 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 ￥16,158
￥21,016 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious Studio Near Sebago Lake
Interior
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 ￥21,857
￥29,270 total
includes taxes & fees
Dec 28 - Dec 29
Rufus III Yurt on the river
Outdoor dining
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 ￥18,734
￥27,227 total
includes taxes & fees
Dec 25 - Dec 26
Allie Mae Yurt nestled in the woods
1 bedroom, iron/ironing board, travel crib, free WiFi
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 ￥21,310
￥26,632 total
includes taxes & fees
Dec 30 - Dec 31
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Property grounds
Luxe Lodge in the Woods! With Sauna & Hot tub

Vacation 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 traveler
The price is ￥34,034
￥86,058 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxe Lodge in the Woods! With Sauna & Hot tub
Interior
Clean+Modern Cozy A-frame

Vacation 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 ￥46,774
￥82,975 total
includes taxes & fees
Dec 29 - Dec 30
Clean+Modern Cozy A-frame
Fridge, microwave, oven, stovetop
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 ￥27,057
￥76,853 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Adventure Tower: Family Fun for All Ages!
Fridge, microwave, oven, dishwasher
NEW! Gray Woodland Escape | Golf, Pool & Cinema

Vacation Home in Gray

NEW! Gray Woodland Escape | Golf, Pool & Cinema
10.0 out of 10, Exceptional, (1)
The price is ￥73,985
￥147,380 total
includes taxes & fees
Jan 5 - Jan 6, 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

Vacation 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 ￥42,152
￥80,461 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Exterior
River Access, hot tub, dogs!

Vacation 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 ￥25,653
￥67,164 total
includes taxes & fees
Jan 13 - Jan 14, 2026
River Access, hot tub, dogs!
Outdoor spa tub
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit

Vacation 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 ￥43,557
￥72,322 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Terrace/patio
LUX Designer Private Waterfront Crooked River SEBAGO

Vacation 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.
The price is ￥94,140
￥146,565 total
includes taxes & fees
Dec 25 - Dec 26
LUX Designer Private Waterfront Crooked River SEBAGO
3 bedrooms, iron/ironing board, free WiFi, bed sheets
River’s Ranch

Vacation 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 ￥59,716
￥122,949 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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 3 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
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  • 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 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.