Milton Vacations from $318

Book a Hotel + Flight or Car together to unlock savings

Your Milton Vacation

Excellent adventures await when you reserve a Milton vacation package. Whether you're a foodie, art buff or just a traveler who appreciates new places, there's something for everyone in this vibrant city. There's lots to see during your trip to Milton, including Sunrise Lake and Marchs Pond. Whoever you're taking time off with and whatever the size of your budget, your dream Milton vacation is just clicks away with Expedia.

The Latest Milton vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $479, price is now $318 per person
$318
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The staff are amazing! Love the amenities - the pool, recreation center, activities for the kids such as windchime arts and crafts. The arcade is always a hit. The Loft makes it so easy to not have to stress about a place to go to for dinner. The Cove is a great place for everyone!

Reviewed on Dec 28, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,696, price is now $798 per person
$798
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,587, price is now $922 per person
$922
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,002, price is now $1,183 per person
$1,183
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
I had a blast at Raffles

Reviewed on Jan 12, 2026

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $662, price is now $392 per person
$392
per person
Feb 26 - Mar 3
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

Don't see what you're looking for?
See all available trips from Columbus to Milton
View all trips

Milton Hotel Deals

Garrison Hotel & Suites Dover-Portsmouth, an Ascend Collection Hotel

Garrison Hotel & Suites Dover-Portsmouth, an Ascend Collection Hotel

2.5 out of 5
200 Sterling Way Dover NH
Fully refundable
$94 nightly
The price is $102 total per night from Jan 20 to Jan 21
$102 total
Jan 20 - Jan 21
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Very clean

Reviewed on Jan 8, 2026

Garrison Hotel & Suites Dover-Portsmouth, an Ascend Collection Hotel
Homewood Suites by Hilton Dover

Homewood Suites by Hilton Dover

3 out of 5
21 Members Way Dover NH
$107 nightly
The price is $116 total per night from Jan 22 to Jan 23
$116 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (751 reviews)
Breakfast was great. Hot tub was so hot , it was awesome

Reviewed on Jan 4, 2026

Homewood Suites by Hilton Dover
Holiday Inn Express Hotel & Suites Rochester by IHG

Holiday Inn Express Hotel & Suites Rochester by IHG

2.5 out of 5
77 Farmington Rd Rochester NH
Fully refundable
$103 nightly
The price is $112 total per night from Jan 16 to Jan 17
$112 total
Jan 16 - Jan 17
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
The staff was fantastic and the room was spotless.

Reviewed on Jan 4, 2026

Holiday Inn Express Hotel & Suites Rochester by IHG
See all 940 properties in Milton
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 Milton Vacation Packages

Milton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portsmouth Intl. Airport (PSM)
Population
580
Top Sights
Rochester Opera House, Merrymeeting Lake and Sunrise Lake

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Milton vacation package cost?
Offering great value package deals from $318 on Expedia, you'll be thrilled with how little a vacation to Milton costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Milton?
You can typically find lower prices and better availability in January, September and October. Check out our cheap Milton vacation packages and you could land some great off-season discounts.
How many days is enough for Milton?
With a well-organized itinerary, you can easily hit the main Milton sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Milton vacation for longer.
How to find the best Milton package deals?
Use Expedia's filter tool to find some of the best Milton package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Milton package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Milton vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Milton vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Milton?
If you're planning a spontaneous Milton vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Milton vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Milton vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.