Cheap Vacations in Middlesex County

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Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $683, price is now $501 per person
$501
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,963, price is now $1,220 per person
$1,220
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,449, price is now $931 per person
$931
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,816, price is now $1,224 per person
$1,224
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,512, price is now $1,725 per person
$1,725
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,308, price is now $917 per person
$917
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Inn on Boltwood

Inn on Boltwood

3 out of 5
Price was $954, price is now $676 per person
$676
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,526, price is now $1,104 per person
$1,104
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,606, price is now $1,200 per person
$1,200
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Price was $816, price is now $632 per person
$632
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)

3-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $683, price is now $501 per person
$501
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $1,963, price is now $1,220 per person
$1,220
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,449, price is now $931 per person
$931
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,224 per person
$1,224
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Save 100% on your flight
Price was $2,512, price is now $1,725 per person
$1,725
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
Price was $1,308, price is now $917 per person
$917
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $1,576, price is now $1,124 per person
$1,124
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $1,526, price is now $1,104 per person
$1,104
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,606, price is now $1,200 per person
$1,200
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Price was $816, price is now $632 per person
$632
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Cambridge Common House

Cambridge Common House

4 out of 5
Price was $767, price is now $605 per person
$605
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Save 100% on your flight
Price was $1,621, price is now $1,278 per person
$1,278
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)

4-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $738, price is now $607 per person
$607
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Inn on Boltwood

Inn on Boltwood

3 out of 5
Price was $954, price is now $676 per person
$676
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Price was $1,132, price is now $878 per person
$878
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $2,135, price is now $1,683 per person
$1,683
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Deerfield Inn

Deerfield Inn

3 out of 5
Price was $773, price is now $614 per person
$614
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,444, price is now $1,151 per person
$1,151
per person
Dec 2 - Dec 6
found 2 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Price was $1,832, price is now $1,470 per person
$1,470
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Boston (BOS)
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Price was $832, price is now $688 per person
$688
per person
Dec 2 - Dec 6
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Price was $896, price is now $746 per person
$746
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Old Mill Inn

Old Mill Inn

3 out of 5
Price was $730, price is now $615 per person
$615
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Shelburne Springs Hotel

Shelburne Springs Hotel

2 out of 5
Price was $1,378, price is now $1,168 per person
$1,168
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Sunny G B&B

The Sunny G B&B

2.5 out of 5
Price was $1,294, price is now $1,112 per person
$1,112
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)

5-night Middlesex County vacations

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
Price was $704, price is now $589 per person
$589
per person
Nov 19 - Nov 24
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
Price was $1,325, price is now $806 per person
$806
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $1,250, price is now $872 per person
$872
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,664, price is now $1,335 per person
$1,335
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hyatus Luxury Residences Salem

Hyatus Luxury Residences Salem

4.5 out of 5
Price was $1,012, price is now $827 per person
$827
per person
Nov 19 - Nov 24
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Underwood-Hale House

The Underwood-Hale House

4 out of 5
Price was $1,466, price is now $1,209 per person
$1,209
per person
Nov 19 - Nov 24
found 10 hours ago
Roundtrip flight included
Orange County (SNA) to Providence (PVD)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Price was $906, price is now $748 per person
$748
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hampton Inn & Suites Providence/Warwick-Airport

Hampton Inn & Suites Providence/Warwick-Airport

3.5 out of 5
Price was $985, price is now $840 per person
$840
per person
Nov 19 - Nov 24
found 10 hours ago
Roundtrip flight included
Orange County (SNA) to Providence (PVD)
Omni Parker House

Omni Parker House

4.5 out of 5
Price was $996, price is now $850 per person
$850
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Price was $991, price is now $846 per person
$846
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Bell Inn

The Bell Inn

5 out of 5
Price was $1,044, price is now $898 per person
$898
per person
Nov 19 - Nov 24
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Price was $875, price is now $758 per person
$758
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

6-7 night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $801, price is now $627 per person
$627
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
Price was $1,672, price is now $851 per person
$851
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $2,805, price is now $1,609 per person
$1,609
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Price was $1,562, price is now $1,035 per person
$1,035
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $2,322, price is now $1,711 per person
$1,711
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Price was $1,128, price is now $850 per person
$850
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Save 100% on your flight
Price was $1,583, price is now $1,196 per person
$1,196
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
The Dagny Boston

The Dagny Boston

4 out of 5
Price was $1,262, price is now $1,017 per person
$1,017
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
Price was $846, price is now $683 per person
$683
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Price was $1,215, price is now $992 per person
$992
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
Price was $1,662, price is now $1,366 per person
$1,366
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Price was $1,063, price is now $874 per person
$874
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)

Top places to visit in Middlesex County

An aerial view of a town with a central square, a church, and surrounding residential areas.
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Marlborough

Marlborough

Flight deals to Middlesex County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Feb 5 - Sat, Feb 6
LAX
Los Angeles
BOS
Boston
$291 Roundtrip, found 6 days ago
$291
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Feb 5 from Los Angeles to Boston, returning Sat, Feb 6, priced at $291 found 6 days ago
Tue, Nov 3 - Tue, Nov 17
LAX
Los Angeles
PVD
Providence
$334 Roundtrip, found 3 days ago
$334
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Nov 3 from Los Angeles to Providence, returning Tue, Nov 17, priced at $334 found 3 days ago
Wed, Dec 30 - Thu, Jan 7
PDX
Portland
BOS
Boston
$334 Roundtrip, found 6 hours ago
$334
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Wed, Dec 30 from Portland to Boston, returning Thu, Jan 7, priced at $334 found 6 hours ago

Top rated hotels for your Middlesex County vacation

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Free Cancellation
Reserve now, pay when you stay
2.3 mi from city center
$279 nightly
The price is $312 total per night
$312 total
Nov 11 - Nov 12
Total with taxes and fees
With a stay at Encore Boston Harbor in Everett, you'll be near the airport, steps from Encore Boston Harbor and a 5-minute drive from The Freedom Trail.
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Free Cancellation
Reserve now, pay when you stay
1.71 mi from city center
$136 nightly
The price is $152 total per night
$152 total
Nov 15 - Nov 16
Total with taxes and fees
With a stay at La Quinta Inn & Suites by Wyndham Boston Somerville in Somerville (Assembly Square), you'll be within a 5-minute drive of Assembly Row and Encore Boston Harbor.
Breakfast included
Free airport shuttle
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
1.46 mi from city center
$160 nightly
The price is $186 total per night
$186 total
Nov 15 - Nov 16
Total with taxes and fees
With a stay at Hyatt Regency Boston/Cambridge in Cambridge (MIT), you'll be steps from Massachusetts Institute of Technology and 4 minutes by foot from Boston University.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.