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Hillside Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Hillside holiday rentals

Smart TV, fireplace, books

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

2. 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 HK$1,941
HK$4,622 total
includes taxes & fees
27 Aug - 28 Aug
Relaxing A-Frame with Hot Tub and Lake Access
Outdoor dining

3. Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape
Raymond
10.0 out of 10, Exceptional, (51 reviews)
"Beautiful location and wonderful hosts. Made us feel right at home."
United States
Donna
The price is HK$624
HK$1,504 total
includes taxes & fees
8 Sept - 9 Sept
Sebago Lake Cottage on Raymond Cape
Property grounds

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

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
8.8 out of 10, Excellent, (3 reviews)
"Beautiful room. Great location. Excellent hosts. Only bummer was the bed. Everything else was superb"
United States
Katherine F.
The price is HK$732
HK$1,353 total
includes taxes & fees
8 Sept - 9 Sept
Manor Suite,cozy newly renovated,downtown & beach
Interior

5. 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 HK$863
HK$1,283 total
includes taxes & fees
19 Aug - 20 Aug
Ava Jade yurt nestled in the woods of Brownfield, Maine
Outdoor dining

6. 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 HK$941
HK$1,368 total
includes taxes & fees
20 Aug - 21 Aug
Allie Mae Yurt nestled in the woods
Interior

7. Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (14 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 HK$1,098
HK$1,471 total
includes taxes & fees
19 Aug - 20 Aug
Rufus III Yurt on the river
Interior

8. 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)
"Lovely getaway!"
United States
Victor R.
The price is HK$1,286
HK$3,070 total
includes taxes & fees
15 Sept - 16 Sept
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
1 bedroom, iron/ironing board, WiFi, bed sheets

9. 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 HK$799
HK$1,427 total
includes taxes & fees
14 Sept - 15 Sept
Ell Suite walk to town beach
Property grounds

10. 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 HK$2,471
HK$6,007 total
includes taxes & fees
20 Aug - 21 Aug
Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
Exterior detail

11. 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 HK$738
HK$1,061 total
includes taxes & fees
19 Aug - 20 Aug
This woods cabin is a true wilderness getaway. Get ready to commune with nature.
Terrace/patio

12. 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 HK$1,059
HK$1,616 total
includes taxes & fees
1 Sept - 2 Sept
Sebago Lake studio-style condo with enclosed sunroom and sunset views
Exterior

13. Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn

Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn
Bridgton
10.0 out of 10, Exceptional, (67 reviews)
"great commication and amazing cabin "
United States
Matthew A.
The price is HK$3,130
HK$4,634 total
includes taxes & fees
8 Sept - 9 Sept
Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn
Living area

14. 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, (6 reviews)
"Beautiful scenery all around the area. House was quiet and conveniently located"
United States
Laura
The price is HK$1,177
HK$2,197 total
includes taxes & fees
15 Sept - 16 Sept
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Outdoor dining

15. 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, (14 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is HK$1,836
HK$2,292 total
includes taxes & fees
24 Aug - 25 Aug
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Coffee/tea maker, fridge, microwave, oven

16. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (1 review)
"Very nice stay thank you. Lots if local things to do nearby."
United States
Bob P.
The price is HK$1,922
HK$2,394 total
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Terrace/patio

17. 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
The price is HK$1,765
HK$2,197 total
includes taxes & fees
17 Sept - 18 Sept
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Terrace/patio

18. Secluded A-Frame Cabin Retreat in Oxford

Secluded A-Frame Cabin Retreat in Oxford
Oxford
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay."
United States
Justin P.
The price is HK$1,875
HK$3,300 total
includes taxes & fees
1 Sept - 2 Sept
Secluded A-Frame Cabin Retreat in Oxford
Beach nearby

19. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is HK$1,490
HK$4,173 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Family Home w/ Beach Access
Dining

20. 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 HK$2,157
HK$4,532 total
includes taxes & fees
15 Sept - 16 Sept
Dream Lakefront Modern Cabin
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
"Great place! Close to St Joseph College"
Julia 1-night trip
Posted 5 hours ago
Dormir

Find out more about Hillside

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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?

Lake Cabin | Fire Pit | Direct Lake Access | Pool | Near Ski Area: This holiday home rental outside of Hillside is located on a lake, and has a balcony, a garden and a BBQ 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 that 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 wider area, you’ll find Sebago Cove and Trickey Pond.

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.