Round Pond Vacations from $458
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Round Pond Vacation Packages
- Harborline Hotel
Oct 9 - Oct 12Harborline Hotel + Flight
Rockland3 nights3.0 star property7.4/10 - Good (312 reviews)"Personnel pas très serviable . Rien de disponible pour petit déjeuner . Air clim très bruyant . Chambre très chaude a l’arrivée ."Reviewed August 6, 2026Roundtrip • New York (EWR) - Rockland (RKD)EWR - BOS • Nonstop BOS - EWR • Nonstop$618$458found 1 day agoper traveler - Topside Inn
Sep 27 - Oct 1Topside Inn + Flight
Boothbay Harbor4 nights3.0 star property10/10 - Exceptional (137 reviews)"What a beautiful property! We will definitely be back again, thank you so much!"Reviewed August 3, 2026Roundtrip • Philadelphia (PHL) - Augusta (AUG)TTN - BOS • 1 stop BOS - PHL • 1 stop - Mid-Town Motel
Oct 12 - Oct 16Mid-Town Motel + Flight
Boothbay Harbor4 nights2.0 star property8.6/10 - Excellent (256 reviews)"What a beauty!! The hosts were wonderful—helpful and so kind. The motel is literally up the hill from everything in Boothbay Harbor. The price was so affordable and one night wasn’t long enough!! Thank you Mid-Town! We shall return!!"Reviewed August 6, 2026Roundtrip • Philadelphia (PHL) - Augusta (AUG)PHL - BOS • Nonstop BOS - PHL • 1 stop$805$643found 1 day agoper traveler - Linekin Bay Resort
Sep 27 - Oct 1Linekin Bay Resort + Flight
Boothbay Harbor4 nights3.0 star property9.2/10 - Wonderful (231 reviews)"Very clean, lots to do, plenty of quiet spaces for relaxation as well. Breakfast was delicious."Reviewed August 3, 2026Roundtrip • Philadelphia (PHL) - Augusta (AUG)TTN - BOS • 1 stop BOS - PHL • 1 stop$901$721found 23 hours agoper traveler - Grand Summit Hotel
Oct 16 - Oct 20Grand Summit Hotel + Flight
Newry4 nights3.0 star property8.4/10 - Very Good (392 reviews)"Great place for a fun family vacation. Wish we could’ve stayed longer!"Reviewed August 5, 2026Roundtrip • New York (NYC) - Augusta (AUG)JFK - BOS • Nonstop BOS - JFK • Nonstop$590$481found 1 day agoper traveler
Round Pond Hotel Deals
"Excellent as in prior years."
"Room on first floor with parking right in front of the door."
Cod Cove Inn, BW Signature Collection
Cod Cove Inn, BW Signature Collection
"Very clean, lots to do, plenty of quiet spaces for relaxation as well. Breakfast was delicious."
"I’ve never been to a Bed and Breakfast place before, but if they are all like this place I will only be booking these from now on. It was amazing!!!"
"The location is great!"
Frequently Asked Questions
How much does a Round Pond vacation package cost?
You'll find cheap prices from $458 on Expedia for your Round Pond getaway. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Round Pond costs.
What are the cheapest months to go to Round Pond?
If you'd like to snag a cheap Round Pond vacation package, consider visiting in October, November and December. You'll generally find lower rates on flights and accommodations during these months — perfect for travelers wishing to save money.
How many days is enough for Round Pond?
Generally, a handful of days is enough to explore the major attractions during your Round Pond vacation. But if you'd like to have more time to chill out or take day trips, think about extending your trip.
How to find the best Round Pond package deals?
Use Expedia's filters to find some of the best Round Pond package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Round Pond package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Round Pond vacation as a package?
You can enjoy significant savings on your next Round Pond escape by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Round Pond?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Round Pond escape.
Does Expedia offer Book Now, Pay Later Round Pond vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Round Pond trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.