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Hillside Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Hillside vacation rentals

TV

Spacious Family Home w/ Long Lake Access

Spacious Family Home w/ Long Lake Access
Naples
The price is SAR 2,437
SAR 4,601 total
includes taxes & fees
25 Jul - 26 Jul
Spacious Family Home w/ Long Lake Access
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 SAR 1,436
SAR 1,963 total
includes taxes & fees
2 Jul - 3 Jul
Artsy Woodland Group Hideaway Cabin!
Property grounds

Secluded A-Frame Cabin Near Ponds Oxford

Secluded A-Frame Cabin Near Ponds Oxford
Oxford
The price is SAR 935
SAR 1,629 total
includes taxes & fees
1 Jul - 2 Jul
Secluded A-Frame Cabin Near Ponds Oxford
House (3 Bedrooms) | Interior

Dock & Beach Access! Waterfront Home on Kezar Lake

Dock & Beach Access! Waterfront Home on Kezar Lake
3.0 star property
Lovell
The price is SAR 2,494
SAR 3,957 total
includes taxes & fees
5 Jul - 6 Jul
Dock & Beach Access! Waterfront Home on Kezar Lake
Property grounds

Glamping A-Frame Cabin with Cold Plunge + Hot Tub

Glamping A-Frame Cabin with Cold Plunge + Hot Tub
Oxford
The price is SAR 973
SAR 1,674 total
includes taxes & fees
7 Jul - 8 Jul
Glamping A-Frame Cabin with Cold Plunge + Hot Tub
Property grounds

Kayak, Paddleboard, or Boat to Restaurants & Ice Cream on Long Lake

Kayak, Paddleboard, or Boat to Restaurants & Ice Cream on Long Lake
Bridgton
10.0 out of 10, Exceptional, (45 reviews)
"We had a wonderful weekend stay at Cosmo’s Cottage. Julia and Tony went above and beyond to make sure we were comfortable and had everything needed to enjoy our stay. The location on the lake is perfect and accommodations were even better than expected. We will definitely be coming back! "
United States
Tyler S.
Kayak, Paddleboard, or Boat to Restaurants & Ice Cream on Long Lake
Property grounds

Modern Glamping Cabin with Hot tub

Modern Glamping Cabin with Hot tub
Oxford
The price is SAR 916
SAR 1,605 total
includes taxes & fees
5 Jul - 6 Jul
Modern Glamping Cabin with Hot tub
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 SAR 1,803
SAR 2,947 total
includes taxes & fees
30 Jun - 1 Jul
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Exterior detail

1 bedroom cottage with queen bed and 2 person whirlpool tub.

1 bedroom cottage with queen bed and 2 person whirlpool tub.
Norway
The price is SAR 575
SAR 716 total
includes taxes & fees
28 Jun - 29 Jun
1 bedroom cottage with queen bed and 2 person whirlpool tub.
Property grounds

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.
Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
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 SAR 1,959
SAR 2,757 total
includes taxes & fees
29 Jun - 30 Jun
Lakefront Log Home 12 feet Away from Lake
Exterior

Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago

Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago
Sebago
The price is SAR 1,393
SAR 3,606 total
includes taxes & fees
5 Jul - 6 Jul
Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago
Outdoor spa tub

Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️

Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Norway
9.6 out of 10, Exceptional, (18 reviews)
"Wonderful spot!!! The host was so helpful "
United States
Sue W.
The price is SAR 2,816
SAR 4,208 total
includes taxes & fees
16 Jul - 17 Jul
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Apartment (0 Bedroom) | Interior

Stay on Historic Estate! Quiet Limerick Escape

Stay on Historic Estate! Quiet Limerick Escape
3.0 star property
Limerick
The price is SAR 680
SAR 1,116 total
includes taxes & fees
9 Jul - 10 Jul
Stay on Historic Estate! Quiet Limerick Escape
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, (9 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
The price is SAR 879
SAR 1,089 total
includes taxes & fees
20 Jul - 21 Jul
THE LILLIPAD.Off-grid A frame. Sebago lake region!
TV, fireplace

Little Acorn Landing

Little Acorn Landing
Norway
The price is SAR 638
SAR 798 total
includes taxes & fees
28 Jun - 29 Jun
Little Acorn Landing
Dining

Family, friends, Gathering

Family, friends, Gathering
Standish
8.0 out of 10, Very Good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is SAR 2,704
SAR 6,140 total
includes taxes & fees
9 Jul - 10 Jul
Family, friends, Gathering
Terrace/patio

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Naples
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
United States
Gina P.
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Fridge, microwave, oven, stovetop

Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
9.6 out of 10, Exceptional, (5 reviews)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveler
The price is SAR 1,408
SAR 3,783 total
includes taxes & fees
1 Jul - 2 Jul
Waterfront Access with Kayaks, Private Deck and a Firepit
Outdoor dining

Peaceful 2-bedroom apartment In updated farmhouse!

Peaceful 2-bedroom apartment In updated farmhouse!
Lovell
10.0 out of 10, Exceptional, (1 review)
"Great spot for a short stay right down the road from Kezar Lake. If you’re taller than 6’4”, just watch your head"
United States
Seth
The price is SAR 612
SAR 876 total
includes taxes & fees
28 Jun - 29 Jun
Peaceful 2-bedroom apartment In updated farmhouse!
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 155 Acres - Pickleball, Reunions & Weddings

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings

10/10 Excellent
"This place had most everything. The lake/pond was wonderful and there were enough kayaks, canoes and a boat for everyone. The new pickleball courts were great and the house was big enough for everyone to have their own space."
Dorothy U. 4-night trip
Posted 10 hours ago
Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings

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 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.