Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Hillside vacation rentals

Property grounds

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is ￥11,340
￥23,346 total
includes taxes & fees
Mar 4 - Mar 5
Manor Suite,cozy newly renovated,downtown & beach
Dining

Lake Front Cabin on Desirable Highland Lake

Lake Front Cabin on Desirable Highland Lake
Bridgton
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful place to stay with all the amenities."
United States
Paul J.
The price is ￥28,684
￥64,437 total
includes taxes & fees
Mar 1 - Mar 2
Lake Front Cabin on Desirable Highland Lake
Exterior

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

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
10.0 out of 10, Exceptional, (14 reviews)
"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 ￥25,428
￥100,123 total
includes taxes & fees
Mar 1 - Mar 2
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
1 bedroom, desk, free WiFi, bed sheets

Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake
Windham
10.0 out of 10, Exceptional, (4 reviews)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is ￥20,932
￥26,196 total
includes taxes & fees
Feb 24 - Feb 25
Spacious Studio Near Sebago Lake
1 bedroom, iron/ironing board, travel crib, free WiFi

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Bridgton
10.0 out of 10, Exceptional, (21 reviews)
"Stay was great, as advertised."
United States
Mary Campbell K.
The price is ￥21,164
￥26,450 total
includes taxes & fees
Feb 24 - Feb 25
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
1 bedroom, desk, free WiFi, bed sheets

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Norway
10.0 out of 10, Exceptional, (8 reviews)
"Such a great and cozy few days away from reality, highly recommend this warm, home away from home kind of place!"
United States
Elizabeth S.
The price is ￥69,773
￥115,938 total
includes taxes & fees
Feb 24 - Feb 25
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Interior

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (12 reviews)
"Had a great time,will be back for sure. "
United States
John C.
The price is ￥21,707
￥29,069 total
includes taxes & fees
Feb 24 - Feb 25
Rufus III Yurt on the river
Exterior

Cozy Winter Stay • Nut House • Near Mt & Bridgton

Cozy Winter Stay • Nut House • Near Mt & Bridgton
Bridgton
10.0 out of 10, Exceptional, (2 reviews)
"What a great little house...everything was well appointed and planned. Very easy to find and communication was excellent. Inspiring layout of home---i hope to build one like it someday."
United States
Laura H.
The price is ￥22,792
￥46,263 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Winter Stay • Nut House • Near Mt & Bridgton
Interior

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, (17 reviews)
"A lovely, cozy yurt in the peaceful Maine forest! We only spent one night to break up a longer drive, but we loved relaxing by the wood stove and the comfy bed. Thanks for a great stay!"
United States
Sonia E.
The price is ￥17,056
￥25,351 total
includes taxes & fees
Feb 24 - Feb 25
Ava Jade yurt nestled in the woods of Brownfield, Maine
Outdoor dining

Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods
Brownfield
10.0 out of 10, Exceptional, (21 reviews)
"We really enjoyed our stay. The wood stove was perfect. Would definitely go back."
United States
Alfred C.
The price is ￥18,606
￥27,041 total
includes taxes & fees
Feb 24 - Feb 25
Allie Mae Yurt nestled in the woods
Fridge, microwave, oven, stovetop

Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
10.0 out of 10, Exceptional, (4 reviews)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveler
The price is ￥27,754
￥117,795 total
includes taxes & fees
Mar 2 - Mar 3
Waterfront Access with Kayaks, Private Deck and a Firepit
Interior

Clean+Modern Cozy A-frame

Clean+Modern Cozy A-frame
Fryeburg
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful super cute cottge. Would definitely stay here everytime I vist the area!!!"
United States
Denise C.
The price is ￥26,047
￥59,488 total
includes taxes & fees
Feb 25 - Feb 26
Clean+Modern Cozy A-frame
Exterior

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Brownfield
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥21,831
￥45,935 total
includes taxes & fees
Mar 2 - Mar 3
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Outdoor spa tub

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

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Conway
9.8 out of 10, Exceptional, (177 reviews)
"Great place, location."
United States
Jonathan N.
The price is ￥41,864
￥80,751 total
includes taxes & fees
Feb 24 - Feb 25
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Private kitchen

LUXURY CAMPING IN THE HEART OF THE MAINE LAKES REGION MINUTES TO NAPLES CAUSEWAY

LUXURY CAMPING IN THE HEART OF THE MAINE LAKES REGION MINUTES TO NAPLES CAUSEWAY
Casco
The price is ￥28,684
￥49,687 total
includes taxes & fees
Feb 24 - Feb 25
LUXURY CAMPING IN THE HEART OF THE MAINE LAKES REGION MINUTES TO NAPLES CAUSEWAY
Exterior

Lakefront Log Home 12 feet Away from Lake

Lakefront Log Home 12 feet Away from Lake
Bridgton
10.0 out of 10, Exceptional, (64 reviews)
"great commication and amazing cabin "
United States
Matthew A.
The price is ￥58,609
￥84,502 total
includes taxes & fees
Mar 2 - Mar 3
Lakefront Log Home 12 feet Away from Lake
Outdoor spa tub

Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit

Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Sebago
10.0 out of 10, Exceptional, (3 reviews)
"Lovely, comfortable home equipped with anything you could need. Hosts were helpful and easy to reach. "
United States
Rebecca D.
The price is ￥43,259
￥70,982 total
includes taxes & fees
Feb 24 - Feb 25
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Exterior

A-Frame Hot tub Retreat - Firepit, Grill, EV & Dog Friendly, Close to N. Conway.

A-Frame Hot tub Retreat - Firepit, Grill, EV & Dog Friendly, Close to N. Conway.
Fryeburg
9.2 out of 10, Wonderful, (10 reviews)
"Really cute, had everything we needed. Super clean. Would definitely stay again!! "
United States
Jane A.
The price is ￥28,864
￥71,684 total
includes taxes & fees
Feb 25 - Feb 26
A-Frame Hot tub Retreat - Firepit, Grill, EV & Dog Friendly, Close to N. Conway.
TV, books

New England Hideaway on Historic 1859 Estate!

New England Hideaway on Historic 1859 Estate!
Limerick
10.0 out of 10, Exceptional, (2 reviews)
"The apartment allowed us the privacy we were looking for and a great location while visiting our son. We will be back for sure."
United States
Carl E.
The price is ￥30,390
￥57,620 total
includes taxes & fees
Feb 24 - Feb 25
New England Hideaway on Historic 1859 Estate!
Interior

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, (58 reviews)
"Lovely getaway!"
United States
Victor R.
The price is ￥20,467
￥53,744 total
includes taxes & fees
Mar 17 - Mar 18
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
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

Oxford Casino Hotel

Oxford Casino Hotel

10/10 Excellent
"Everything was fine."
William 1-night trip
Posted 2 days ago
Oxford Casino Hotel

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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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?

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your 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 Sebago Cove 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.