Monroe Vacations from $540

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The Latest Monroe 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 14 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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Monroe Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 11 to May 12
$120 total
May 11 - May 12
Total with taxes and fees
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$147 nightly
The price is $164 total per night from May 18 to May 19
$164 total
May 18 - May 19
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
The property was clean and the staff was polite, but I was disappointed that I was placed in an accessible room even though I did not request one. I asked if another room was available and was told the hotel was fully booked. While I understand availability issues happen, the room layout was not ...

Reviewed on May 7, 2026

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $298 total per night from May 11 to May 12
$298 total
May 11 - May 12
Total with taxes and fees
9.6/10 Exceptional! (623 reviews)
Very nice understated hotel. Great staff. Nice restaurant. Walkable to coffe house and restaurants and campus. Wonderful for college community. Kudos to management staff. Really really nice.

Reviewed on May 6, 2026

The Williams Inn
See all 1,348 properties in Monroe
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 Monroe Vacation Packages

Monroe Essential Information

Language
English
Currency
U.S dollars
Top Sights
Bissell Covered Bridge, Hawley Bog Preserve and Charlemont Federated Church

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Frequently asked questions

How much does a Monroe vacation package cost?
Offering excellent value package deals from $540 on Expedia, you'll be thrilled with how little a vacation to Monroe costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Monroe?
You can typically find lower prices and greater availability in June, November and December. Take a look at our cheap Monroe vacation packages and you could get some excellent off-season deals.
How many days is enough for Monroe?
The ideal duration of your Monroe vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to hit all the leading sights and discover some hidden spots along the way.
How to find the best Monroe package deals?
Begin your search for a Monroe package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Monroe package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Monroe adventure underway.
Is it cheaper to book a Monroe vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Monroe getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Monroe?
If you've got your Monroe travel dates confirmed, book as soon as you can to score some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Monroe vacation packages?
Jet off on your dream escape to Monroe with our Book Now, Pay Later vacations. No need to save like crazy or wait for your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.