Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Hillside vacation rentals

Outdoor dining

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, (8 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
The price is ￥23,094
￥28,645 total
includes taxes & fees
Apr 13 - Apr 14
THE LILLIPAD.Off-grid A frame. Sebago lake region!
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 ￥11,649
￥23,981 total
includes taxes & fees
Apr 13 - Apr 14
Manor Suite,cozy newly renovated,downtown & beach
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, (19 reviews)
"Beautiful , clean , secluded Yurt . We truly enjoyed our stay "
United States
Judy S.
The price is ￥17,520
￥26,041 total
includes taxes & fees
Apr 13 - Apr 14
Ava Jade yurt nestled in the woods of Brownfield, Maine
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 ￥22,298
￥29,860 total
includes taxes & fees
Apr 13 - Apr 14
Rufus III Yurt on the river
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 ￥26,415
￥61,926 total
includes taxes & fees
Apr 13 - Apr 14
Lake Front Cabin on Desirable Highland Lake
1 bedroom, iron/ironing board, travel crib, free WiFi

Barn on Pleasant-walk to Highland beach & town

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (22 reviews)
"My wife and I enjoyed our stay very much and it exceeded our expectations. Very clean and comfortable. Would definitely stay here again and have already told friends about it."
United States
Tom L.
The price is ￥25,085
￥30,816 total
includes taxes & fees
Apr 13 - Apr 14
Barn on Pleasant-walk to Highland beach & town
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 ￥19,112
￥27,776 total
includes taxes & fees
Apr 13 - Apr 14
Allie Mae Yurt nestled in the woods
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 ￥32,013
￥119,830 total
includes taxes & fees
Apr 13 - Apr 14
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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 ￥25,324
￥116,447 total
includes taxes & fees
Apr 13 - Apr 14
Waterfront Access with Kayaks, Private Deck and a Firepit
Living area

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Lovell
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful scenery all around the area. House was quiet and conveniently located"
United States
Laura
The price is ￥19,112
￥38,713 total
includes taxes & fees
Apr 13 - Apr 14
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Dining

Dream Lakefront Modern Cabin

Dream Lakefront Modern Cabin
West Bridgton
10.0 out of 10, Exceptional, (11 reviews)
"This was a beautiful property! Very clean and relaxing! "
United States
Mary G.
The price is ￥26,941
￥70,162 total
includes taxes & fees
Apr 13 - Apr 14
Dream Lakefront Modern Cabin
Terrace/patio

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, (2 reviews)
"Great house, we had a wonderful time!"
United States
Alex F.
The price is ￥21,900
￥71,960 total
includes taxes & fees
Apr 23 - Apr 24
Relaxing A-Frame with Hot Tub and Lake Access
Terrace/patio

Modern Glamping Cabin with Hot tub

Modern Glamping Cabin with Hot tub
Oxford
The price is ￥31,854
￥58,852 total
includes taxes & fees
May 3 - May 4
Modern Glamping Cabin with Hot tub
Property grounds

Rustic A-Frame Getaway with Hot Tub

Rustic A-Frame Getaway with Hot Tub
Oxford
Rustic A-Frame Getaway with Hot Tub
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 ￥23,891
￥58,852 total
includes taxes & fees
May 6 - May 7
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
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 ￥61,797
￥106,767 total
includes taxes & fees
Apr 14 - Apr 15
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
TV, books, stereo

Artsy Woodland Group Hideaway Cabin!

Artsy Woodland Group Hideaway Cabin!
Parsonsfield
8.4 out of 10, Very Good, (6 reviews)
"It's not the most modern place but it is a good value, has what you need and is in a beautiful setting "
United States
Dan F.
The price is ￥60,921
￥83,244 total
includes taxes & fees
Apr 13 - Apr 14
Artsy Woodland Group Hideaway Cabin!
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 ￥22,425
￥47,880 total
includes taxes & fees
Apr 27 - Apr 28
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Outdoor dining

Peaceful 2-bedroom apartment In updated farmhouse!

Peaceful 2-bedroom apartment In updated farmhouse!
Lovell
The price is ￥20,068
￥30,034 total
includes taxes & fees
Apr 13 - Apr 14
Peaceful 2-bedroom apartment In updated farmhouse!
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
9.4 out of 10, Exceptional, (11 reviews)
"The cabin was super cozy and my girlfriend loved it. We are pleased with the facilities and would love to visit again. The hot tub was quite clean, something I appreciate! Thanks Connie- Best Shea J"
United States
Shea J.
The price is ￥28,159
￥71,837 total
includes taxes & fees
Apr 13 - Apr 14
A-Frame Hot tub Retreat - Firepit, Grill, EV & Dog Friendly, Close 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

Hampton Inn Oxford

Hampton Inn Oxford

10/10 Excellent
"The room was nice. Easy check in and out."
Tammy 2-night trip
Posted 2 days ago
Hampton Inn Oxford

Find out more about Hillside

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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?

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings: This vacation home rental near Hillside is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 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 library and a hot tub.

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.