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Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Hillside vacation rentals

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.
$714 nightly
The price is $778
Jul 24 - Jul 25
Total with taxes and fees
Kayak, Paddleboard, or Boat to Restaurants & Ice Cream on Long Lake
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
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, (9 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.
$857 nightly
The price is $934
Jul 19 - Jul 20
Total with taxes and fees
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Iron/ironing board, travel crib, free WiFi, bed sheets

Peaceful Barn Loft near Sebago Lake and Conway, NH

Peaceful Barn Loft near Sebago Lake and Conway, NH
Hiram
$174 nightly
The price is $189
Jul 29 - Jul 30
Total with taxes and fees
Peaceful Barn Loft near Sebago Lake and Conway, NH
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, (10 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
$265 nightly
The price is $289
Jul 14 - Jul 15
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Terrace/patio

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
$257 nightly
The price is $280
Jul 13 - Jul 14
Total with taxes and fees
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Iron/ironing board, travel crib, free WiFi, bed sheets

Barn on Pleasant-walk to Highland beach & town

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
$180 nightly
The price is $196
Jul 13 - Jul 14
Total with taxes and fees
Barn on Pleasant-walk to Highland beach & town
Terrace/patio

Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit

Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit
Windham
$1,176 nightly
The price is $1,282
Jul 13 - Jul 14
Total with taxes and fees
Sebago Basin Retreat | Sleeps 12 | Beach Access | Mooring | Kayaks | Fire Pit
Exterior

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Casco
$280 nightly
The price is $305
Jul 13 - Jul 14
Total with taxes and fees
Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Apartment (0 Bedroom) | Interior

Stay on Historic Estate! Quiet Limerick Escape

Stay on Historic Estate! Quiet Limerick Escape
3.0 star property
Limerick
$273 nightly
The price is $297
Jul 13 - Jul 14
Total with taxes and fees
Stay on Historic Estate! Quiet Limerick Escape
Terrace/patio

Secluded A-Frame Cabin Retreat in Oxford

Secluded A-Frame Cabin Retreat in Oxford
Oxford
10.0 out of 10, Exceptional, (2 reviews)
"Peaceful, beautiful, and everything we wanted ( exception of rain)! Would highly recommend and ca not wait to go back!"
United States
Kelly S.
$369 nightly
The price is $402
Jul 13 - Jul 14
Total with taxes and fees
Secluded A-Frame Cabin Retreat in Oxford
Property grounds

Modern Glamping Cabin with Hot tub

Modern Glamping Cabin with Hot tub
Oxford
$371 nightly
The price is $404
Jul 13 - Jul 14
Total with taxes and fees
Modern Glamping Cabin with Hot tub
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
$220 nightly
The price is $239
Jul 13 - Jul 14
Total with taxes and fees
Peaceful 2-bedroom apartment In updated farmhouse!
Outdoor dining

Minnow Cottage on the Stunning West Shore of Sebago Lake

Minnow Cottage on the Stunning West Shore of Sebago Lake
Sebago
$354 nightly
The price is $386
Jul 26 - Jul 27
Total with taxes and fees
Minnow Cottage on the Stunning West Shore of Sebago Lake
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.
$703 nightly
The price is $766
Aug 9 - Aug 10
Total with taxes and fees
Lakefront cabin on Brandy Pond with dock, deck, firepit, kayaks & paddleboard
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.
$1,508 nightly
The price is $1,644
Jul 16 - Jul 17
Total with taxes and fees
Family, friends, Gathering
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.
$924 nightly
The price is $1,007
Jul 16 - Jul 17
Total with taxes and fees
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Property grounds

Secluded A-Frame Cabin Near Ponds Oxford

Secluded A-Frame Cabin Near Ponds Oxford
Oxford
$371 nightly
The price is $404
Jul 15 - Jul 16
Total with taxes and fees
Secluded A-Frame Cabin Near Ponds Oxford
TV, fireplace

Little Acorn Landing

Little Acorn Landing
Norway
$213 nightly
The price is $232
Jul 13 - Jul 14
Total with taxes and fees
Little Acorn Landing
TV, books, stereo

Artsy Woodland Group Hideaway Cabin!

Artsy Woodland Group Hideaway Cabin!
Parsonsfield
8.4 out of 10, Very Good, (7 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.
$481 nightly
The price is $524
Jul 13 - Jul 14
Total with taxes and fees
Artsy Woodland Group Hideaway 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

Hampton Inn Oxford

Hampton Inn Oxford

8/10 Good
"Good breakfast, nice rooms. Site was a bit noisy, even near McCarran airport. We arrived"
Dale 2-night trip
Posted 4 hours ago
Hampton Inn Oxford

Find out more about Hillside

Everything you need to know about Hillside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $197 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.