Milton Vacations from $540

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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 Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $797, price is now $540 per person
$540
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (1,185 reviews)
Conveniently located in Beverly

Reviewed on Apr 27, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $4,498, price is now $2,771 per person
$2,771
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,411, price is now $907 per person
$907
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (77 reviews)
New hotel, very good curation of products and decor. Staff is very friendly.

Reviewed on May 7, 2026

enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $1,265, price is now $849 per person
$849
per person
Jul 21 - Jul 26
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (1,009 reviews)
Clean room, helpful staff!

Reviewed on May 5, 2026

The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $1,323, price is now $896 per person
$896
per person
Jul 19 - Jul 25
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (1,000 reviews)
Beautifully kept old style hotel. Great woodwork natural light, sitting rooms with fireplaces. Rooms are clean and well maintained, nice breakfast/ buffet. Excellent location

Reviewed on May 8, 2026

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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
$120 nightly
The price is $130 total per night from May 25 to May 26
$130 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
The staff was very helpful. The hotel and room was clean. They had a very nice selection of Hartley & Son's Tea which was a nice break from the same ol' Bigelow. I don't eat breakfast, so can't comment. Even though the room was clean and nice - if you get a room in the front of the hotel by the parking ...

Reviewed on May 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
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $164 total per night from May 25 to May 26
$164 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (801 reviews)
Room was ok, the fridge had a cracked door and one of the beds had stained sheets. breakfast was plentiful. Most annoying thing is we booked this hotel because it had a pool and hot tub but it was under renovation and at no point in time did we get any heads up that it was not going to be open during ...

Reviewed on May 8, 2026

Homewood Suites by Hilton Dover
Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location

Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location

Wakefield NH
9.4/10 Exceptional! (74 reviews)
Beautiful scenery

Reviewed on Oct 26, 2025

Get rates
Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location
See all 974 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

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Frequently asked questions

How much does a Milton vacation package cost?
Offering great value package deals from $540 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.