Pleasant Ridge Vacations from $779

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Your Pleasant Ridge Vacation

Let our vacation packages to Pleasant Ridge inspire your next great adventure. You'll find loads to love about this exciting city, starting with the neighborhood of Pleasant Pond, which is good for fishing and hiking. There's plenty to add to your itinerary during your trip to Pleasant Ridge, beginning with popular attractions such as Wyman Lake and Houston Brook Falls. A couple of quick clicks is all it takes to build your perfect Pleasant Ridge vacation on Expedia.

The Latest Pleasant Ridge vacation packages

Price found within the past 48 hours. Click for updated prices.
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Price was $925, price is now $779 per person
$779
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (868 reviews)
Clean, classy, and comfortable. Great lobby area to relax by the fire. Complementary coffee. Rooms are large and luxurious.

Reviewed on Jan 31, 2026

Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
Price was $1,674, price is now $1,193 per person
$1,193
per person
May 3 - May 9
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Augusta (AUG)
9/10 Wonderful! (13 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

Mid-Town Motel

Mid-Town Motel

2 out of 5
Price was $1,136, price is now $930 per person
$930
per person
May 3 - May 9
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Augusta (AUG)
8.8/10 Excellent! (213 reviews)
I was in room #2 The room was big, bed was comfortable, water was hot and good pressure. Great distance for walking to town. The windows were open when I arrived, nice breeze but the cigarette smell from the neighbor not so enjoyable. A fridge would have been nice in the room As would have coffee (waiting on office for others to make theirs was not enjoyable) WALLS are paper thin. You can hear everything. Towels ( face towel in particular) had brown stains on them

Reviewed on Oct 20, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $1,014, price is now $840 per person
$840
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (142 reviews)
Clean, quiet, and comfortable. Very nice setting in the carriage house, enjoyable stay.

Reviewed on Nov 1, 2025

Admirals Quarters Inn

Admirals Quarters Inn

2 out of 5
Price was $1,794, price is now $1,515 per person
$1,515
per person
May 3 - May 9
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Augusta (AUG)
9.4/10 Exceptional! (28 reviews)
The room was great. Lots of space. The bed was super comfortable. The breakfast items were delicious. We enjoyed the many selections of tea and coffee. The proprietor,Jersey was terrific. He explained the property and area Had a wonderful time

Reviewed on Dec 1, 2025

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Discover the most popular places to visit in Pleasant Ridge

Wyman Lake

Commune with nature and explore the great outdoors at Wyman Lake during your travels in Bingham.

Wyman Lake

Houston Brook Falls

Explore the great outdoors at Houston Brook Falls, a lovely green space in Bingham.

Houston Brook Falls

Pleasant Ridge Hotel Deals

Sugarloaf Mountain Hotel

Sugarloaf Mountain Hotel

3.5 out of 5
5092 Access Road Kingfield ME
$170 nightly
The price is $185 total per night from Mar 10 to Mar 11
$185 total
Mar 10 - Mar 11
Total with taxes and fees
9/10 Wonderful! (566 reviews)
clean room

Reviewed on Feb 6, 2026

Sugarloaf Mountain Hotel
Sugarloaf Inn

Sugarloaf Inn

3 out of 5
5000 Commons Circle Kingfield ME
$180 nightly
The price is $196 total per night from Feb 11 to Feb 12
$196 total
Feb 11 - Feb 12
Total with taxes and fees
8.2/10 Very Good! (200 reviews)
Staff was excellent - especially Orlando in the restaurant and Debbie at the bar. Room was clean, convenient location for ski in and ski out

Reviewed on Jan 17, 2026

Sugarloaf Inn
Hillholm Estate

Hillholm Estate

3.5 out of 5
33 Winter Hill Street Kingfield ME
$253 nightly
The price is $276 total per night from Feb 12 to Feb 13
$276 total
Feb 12 - Feb 13
Total with taxes and fees
8.8/10 Excellent! (197 reviews)
Gorgeous spot in the world. Wonderful staff, brilliant yoga classes, cozy vibe, great sauna and a super plump cozy bed

Reviewed on Jan 12, 2026

Hillholm Estate
See all 265 properties in Pleasant Ridge
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.

Find the Best Pleasant Ridge Vacation Packages

Pleasant Ridge Essential Information

Language
English
Currency
U.S dollars
Top Sights
Houston Brook Falls and Wyman Lake

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Frequently asked questions

How much does a Pleasant Ridge vacation package cost?
Offering excellent value package deals from $779 on Expedia, you'll be pleasantly surprised at how much a vacation to Pleasant Ridge costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pleasant Ridge?
October, November and December are great times to look for cheap Pleasant Ridge vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Pleasant Ridge?
The ideal length for your Pleasant Ridge vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to hit all the top attractions and explore some hidden gems along the way.
How to find the best Pleasant Ridge package deals?
Begin your search for a Pleasant Ridge package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Pleasant Ridge package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasant Ridge adventure underway.
Is it cheaper to book a Pleasant Ridge vacation as a package?
You can enjoy significant savings on your next Pleasant Ridge escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pleasant Ridge?
If you're planning an impromptu Pleasant Ridge vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Pleasant Ridge vacation packages?
Your Pleasant Ridge trip is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.