Sidney Vacations from $738

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Your Sidney Vacation

Prepare to experience Sidney in your own style with a custom Sidney vacation package! Uncovering the treasures of this lively city is simpler with a base in a neighborhood such as Winslow, which is great for history, among plenty of other things. Like some inspiration on what to see or do first during your trip to Sidney? Check off famous attractions like Thomas College. Browse Expedia's wide range of travel options and book your ideal vacation to Sidney now.

The Latest Sidney vacation packages

Price found within the past 48 hours. Click for updated prices.
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
Price was $914, price is now $738 per person
$738
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
8.2/10 Very Good! (1,007 reviews)
Such an awesome location

Reviewed on Aug 26, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $1,249, price is now $917 per person
$917
per person
Oct 28 - Nov 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (10 reviews)
The location and view of this property was excellent. The staff gave good dining recommendations. The fire pit at night with s’mores was nice. We were given a nice bouquet of flowers at time of check in. The morning breakfast was a bit different. The kitchen was stocked with eggs, cream cheese, yogurt and condiments and pastries. You were responsible to make your own breakfast in the kitchen.

Reviewed on Jul 23, 2025

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,711, price is now $1,378 per person
$1,378
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
10/10 Exceptional! (38 reviews)
The Topside Inn was the perfect place for our stay in Boothbay Harbor. The Carraige House room was very nice and the bed and bedding was amazing! The views of the harbor are spectacular, especially in the quiet of the early morning. However, the star of the show was the incredible breakfast we had each morning! I highly recommend this Inn to anyone traveling to the Boothbay region.

Reviewed on Aug 26, 2025

Admirals Quarters Inn

Admirals Quarters Inn

2 out of 5
Price was $1,157, price is now $970 per person
$970
per person
Nov 22 - Nov 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.6/10 Exceptional! (24 reviews)
Amazing property and the staff was so nice!

Reviewed on Aug 10, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $1,172, price is now $986 per person
$986
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
9.4/10 Exceptional! (128 reviews)
Perfect for convenience, lovely staff and accommodation!

Reviewed on Aug 17, 2025

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Discover the most popular places to visit in Sidney

Old Fort Western showing heritage elements

Old Fort Western

4.5/5(6 reviews)

Learn about life in New England in the 18th and 19th centuries during a guided tour at one of the oldest surviving wooden forts in the USA.

Old Fort Western

Augusta Civic Center

4/5(32 reviews)

After visiting Augusta Civic Center, make a plan to see the other sights and activities in Augusta. Check out the shops and top-notch restaurants in this family-friendly area.

Augusta Civic Center

University of Maine at Augusta

4/5(13 reviews)

Explore the campus of University of Maine at Augusta during your stay in Augusta. Check out the shops and top-notch restaurants in this family-friendly area.

University of Maine at Augusta

Sidney Hotel Deals

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!

2 out of 5
Sidney
9.6/10 Exceptional! (4 reviews)
Beautiful Serene Lakefront Stay
"We enjoyed swimming, kayaking, reading, hiking, listening to the loons, playing games and watching movies on the one rainy day we had. We especially appreciate that we were able to bring our dog who also had a great time!"

Reviewed on Aug 1, 2025

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Private Dock on Messalonskee Lake: Cozy Cottage!
Messalonskee Lakefront Camp Escape with Shared Waterfront Access

Messalonskee Lakefront Camp Escape with Shared Waterfront Access

Sidney
9.4/10 Exceptional! (11 reviews)
"The kids are already asking to book this place for next year!! Friendly, easy-going owner and really nice neighbors. The listing says 2 sets of bunk beds, however, there’s only 1."

Reviewed on Aug 9, 2025

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Messalonskee Lakefront Camp Escape with Shared Waterfront Access
Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $165 total per night from Sep 1 to Sep 2
$165 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"Clean, enjoyed the art"

Reviewed on Aug 25, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
See all 509 properties in Sidney
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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Frequently asked questions

How much does a Sidney vacation package cost?
You'll find cheap prices from $738 on Expedia for your Sidney break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Sidney costs.
What are the cheapest months to go to Sidney?
October, November and December are the best times to look for cheap Sidney vacation packages. Opting to travel in less busy months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Sidney?
Generally, a handful of days is enough to visit the main attractions during your Sidney vacation. However, if you prefer to have more time to relax or go on day trips, think about extending your itinerary.
How to find the best Sidney package deals?
Begin your search for a Sidney package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Sidney package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sidney adventure underway.
Is it cheaper to book a Sidney vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still have the flexibility to create a customized Sidney vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Sidney?
If you're planning an impromptu Sidney getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Sidney vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Sidney trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.