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Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Hillside vacation rentals

1. Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking
Bridgton
10.0 out of 10, Exceptional, (16 reviews)
"Very quaint and quiet, we enjoyed our staying very much would heavily recommend"
United States
Jacob B.
The price is ￥25,642
￥58,851 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking
A wooden cabin with a sloped roof, surrounded by snow-covered trees and a clear sky.

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

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.0 out of 10, Wonderful, (4 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 ￥13,337
￥25,822 total
includes taxes & fees
Sep 8 - Sep 9
Manor Suite,cozy newly renovated,downtown & beach
A cozy interior of a yurt with a central wood-burning stove, a sofa, and a bed with floral bedding.

3. 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, (20 reviews)
"Beautiful , clean , secluded Yurt . We truly enjoyed our stay "
United States
Judy S.
The price is ￥17,512
￥26,029 total
includes taxes & fees
Aug 30 - Aug 31
Ava Jade yurt nestled in the woods of Brownfield, Maine
A bedroom with a stone fireplace, a large bed, a TV, and a wooden floor.

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

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (26 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
The price is ￥27,462
￥34,273 total
includes taxes & fees
Sep 4 - Sep 5
Barn on Pleasant-walk to Highland beach & town
A wooden deck with a checkered mat, two wooden chairs, and a table.

5. 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 ￥39,402
￥90,149 total
includes taxes & fees
Sep 7 - Sep 8
Relaxing A-Frame with Hot Tub and Lake Access
A cozy room with a wooden ceiling, a dining table with chairs, a sofa, and a radiator.

6. Long Lake Cabin: Shared Beach, Grill, Porch

Long Lake Cabin: Shared Beach, Grill, Porch
Naples
The price is ￥31,362
￥73,749 total
includes taxes & fees
Sep 22 - Sep 23
Long Lake Cabin: Shared Beach, Grill, Porch
A cabin with a dock extending into a lake, surrounded by trees.

7. Long Lake 3BR: Beach Access + Dock

Long Lake 3BR: Beach Access + Dock
Naples
The price is ￥27,872
￥79,337 total
includes taxes & fees
Sep 13 - Sep 14
Long Lake 3BR: Beach Access + Dock
A yurt with a wooden porch and two Adirondack chairs, surrounded by a forest.

8. Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods
Brownfield
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful property! Comfortable and clean lodging. "
United States
Ian M.
The price is ￥19,104
￥27,764 total
includes taxes & fees
Aug 30 - Aug 31
Allie Mae Yurt nestled in the woods
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, (15 reviews)
"Fantastic as usual, the owners were very helpful/ friendly and brought more wood over when we asked. We love this spot, we will be back again!"
United States
Jennifer D.
The price is ￥22,288
￥29,847 total
includes taxes & fees
Sep 2 - Sep 3
Rufus III Yurt on the river
A view through a window of a lake surrounded by trees and a small house.

10. 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, (63 reviews)
"This property was nice for a mini family reunion of 3 siblings gathering for a visit after a wedding nearby. It had most everything we needed for an enjoyable stay. Though we did not use them, there were kayaks and a canoe to go explore the lake. It was close to town as well. The deck was perfect for our lobster dinner and accommodated our group well!"
United States
Lorraine M.
The price is ￥25,005
￥60,935 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
A lakeside deck with outdoor seating and a dock extending into the water.

11. Sebago Lake studio-style condo with enclosed sunroom and sunset views

Sebago Lake studio-style condo with enclosed sunroom and sunset views
Standish
9.0 out of 10, Wonderful, (12 reviews)
The price is ￥21,501
￥32,811 total
includes taxes & fees
Sep 1 - Sep 2
Sebago Lake studio-style condo with enclosed sunroom and sunset views
A bedroom with a bed, bedside tables, a chest of drawers, and a patterned rug.

12. Ell Suite walk to town beach

Ell Suite walk to town beach
Bridgton
9.0 out of 10, Wonderful, (2 reviews)
"Great spot as advertised "
United States
mark l.
The price is ￥13,713
￥26,232 total
includes taxes & fees
Sep 14 - Sep 15
Ell Suite walk to town beach
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
The price is ￥22,616
￥75,865 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Family Home w/ Beach Access
A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

14. 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, (15 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is ￥37,253
￥45,638 total
includes taxes & fees
Sep 2 - Sep 3
THE LILLIPAD.Off-grid A frame. Sebago lake region!
A cabin with a stone wall, wooden deck, and a view of a lake.

15. Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard

Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
Naples
9.2 out of 10, Wonderful, (55 reviews)
"Amazing location! Cabin was perfect! Had such a wonderful time. "
United States
Jillene F.
The price is ￥50,170
￥121,963 total
includes taxes & fees
Sep 3 - Sep 4
Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

16. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond
Casco
Fully Updated Lake View Home on Thomas Pond
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

17. 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 ￥35,820
￥44,597 total
includes taxes & fees
Sep 2 - Sep 3
Cozy 2-bedroom house with shared beach access to Sebago Lake
A wooden deck with a grill area, overlooking a lake with trees in the background.

18. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Casco
10.0 out of 10, Exceptional, (1 review)
"An adorable little getaway on the cutest little lake. It is quiet and peaceful."
United States
E Tyler B.
The price is ￥35,820
￥44,423 total
includes taxes & fees
Sep 2 - Sep 3
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
A wooden cabin with a hexagonal window, a wooden door with a diamond pattern, and a hanging basket.

19. This woods cabin is a true wilderness getaway. Get ready to commune with nature.

This woods cabin is a true wilderness getaway. Get ready to commune with nature.
Waterford
The price is ￥14,973
￥21,526 total
includes taxes & fees
Aug 29 - Aug 30
This woods cabin is a true wilderness getaway. Get ready to commune with nature.
A wooden deck with a kitchen area, including a grill, bar stools, and stainless steel appliances, overlooking a forest.

20. Modern Forest Cabin w/ Private Hot Tub & Fire Pit

Modern Forest Cabin w/ Private Hot Tub & Fire Pit
Oxford
10.0 out of 10, Exceptional, (2 reviews)
"My wife and I had a wonderful stay, we took advantage of all the amenities. Cooked in the outdoor kitchen, used the fire pit every night, swam, floated and fished to the pond, hot tub and sauna were wonderful as well. Everything was very clean and new, all cabins have their own space and it was so quiet and peaceful. Already planning another trip!"
United States
Shawn
The price is ￥31,695
￥59,199 total
includes taxes & fees
Sep 1 - Sep 2
Modern Forest Cabin w/ Private Hot Tub & Fire Pit
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

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

10/10 Excellent
"Perfect place for family activities and plenty of space and things to do on the property. My family had a wonderful stay and would absolutely visit again!"
Charlsie H. 5-night trip
Posted 3 days ago
Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

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:

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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?

Lake Cabin | Fire Pit | Direct Lake Access | Pool | Near Ski Area: This vacation home rental near Hillside is located on a lake and has a balcony, a garden, 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.

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 Trickey Pond.

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.