Cheap Vacations in Middlesex County

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Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $926, price is now $564 per person
$564
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Save 100% on your flight
Price was $941, price is now $615 per person
$615
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $2,752, price is now $1,906 per person
$1,906
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Moultonborough Inn

Moultonborough Inn

3 out of 5
Save 100% on your flight
Price was $897, price is now $635 per person
$635
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
Marina Bay Cottages

Marina Bay Cottages

2 out of 5
Save 100% on your flight
Price was $1,711, price is now $1,234 per person
$1,234
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Providence (PVD)
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,103, price is now $816 per person
$816
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Save 100% on your flight
Price was $832, price is now $618 per person
$618
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Save 100% on your flight
Price was $853, price is now $635 per person
$635
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,527, price is now $1,885 per person
$1,885
per person
Jul 18 - Jul 22
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
InnSeason Resorts Pollard Brook

InnSeason Resorts Pollard Brook

3 out of 5
Save 100% on your flight
Price was $1,121, price is now $837 per person
$837
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)

3-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was $656, price is now $499 per person
$499
per person
Jul 14 - Jul 17
found 22 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $926, price is now $564 per person
$564
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,120 per person
$1,120
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Price was $1,194, price is now $849 per person
$849
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,103, price is now $816 per person
$816
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
Price was $836, price is now $622 per person
$622
per person
Jul 14 - Jul 17
found 22 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Price was $1,578, price is now $1,176 per person
$1,176
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Green Harbor Resort

Green Harbor Resort

3 out of 5
Save 100% on your flight
Price was $1,279, price is now $963 per person
$963
per person
Jul 14 - Jul 17
found 22 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Blue Water Resort

Blue Water Resort

3 out of 5
Save 100% on your flight
Price was $1,186, price is now $898 per person
$898
per person
Jul 14 - Jul 17
found 22 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was $689, price is now $528 per person
$528
per person
Jul 14 - Jul 17
found 22 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Save 100% on your flight
Price was $736, price is now $564 per person
$564
per person
Jul 15 - Jul 18
found 18 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,609, price is now $1,234 per person
$1,234
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

4-night Middlesex County vacations

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

The Cove At Salem

3 out of 5
Save 100% on your flight
Price was $907, price is now $709 per person
$709
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,640, price is now $1,629 per person
$1,629
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Save 100% on your flight
Price was $1,426, price is now $988 per person
$988
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $1,639, price is now $1,180 per person
$1,180
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,527, price is now $1,885 per person
$1,885
per person
Jul 18 - Jul 22
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was $1,765, price is now $1,334 per person
$1,334
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Inn at Fireside Tavern Sherborn

The Inn at Fireside Tavern Sherborn

2 out of 5
Price was $4,699, price is now $3,677 per person
$3,677
per person
Jul 22 - Jul 26
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
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 $958, price is now $751 per person
$751
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Bell Inn

The Bell Inn

5 out of 5
Price was $1,103, price is now $871 per person
$871
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
Price was $2,129, price is now $1,685 per person
$1,685
per person
Jul 10 - Jul 14
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,907, price is now $1,509 per person
$1,509
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Price was $2,206, price is now $1,759 per person
$1,759
per person
Jul 18 - Jul 22
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

5-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Price was $864, price is now $628 per person
$628
per person
Jul 8 - Jul 13
found 23 hours ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Save 100% on your flight
Price was $1,642, price is now $1,068 per person
$1,068
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,613, price is now $1,062 per person
$1,062
per person
Jul 8 - Jul 13
found 23 hours ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
Save 100% on your flight
Price was $2,219, price is now $1,525 per person
$1,525
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,453, price is now $1,044 per person
$1,044
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
Price was $2,550, price is now $1,837 per person
$1,837
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
Save 100% on your flight
Price was $1,616, price is now $1,197 per person
$1,197
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Price was $970, price is now $719 per person
$719
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Price was $1,394, price is now $1,037 per person
$1,037
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $2,930, price is now $2,190 per person
$2,190
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Save 100% on your flight
Price was $1,375, price is now $1,036 per person
$1,036
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
The Dagny Boston

The Dagny Boston

4 out of 5
Price was $1,346, price is now $1,019 per person
$1,019
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

6-7 night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Save 100% on your flight
Price was $941, price is now $615 per person
$615
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
Save 100% on your flight
Price was $2,582, price is now $1,446 per person
$1,446
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Save 100% on your flight
Price was $2,159, price is now $1,332 per person
$1,332
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $2,676, price is now $1,683 per person
$1,683
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $2,137, price is now $1,438 per person
$1,438
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,604, price is now $1,106 per person
$1,106
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $2,752, price is now $1,906 per person
$1,906
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Save 100% on your flight
Price was $1,617, price is now $1,131 per person
$1,131
per person
Jul 4 - Jul 11
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Save 100% on your flight
Price was $3,680, price is now $2,599 per person
$2,599
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Moultonborough Inn

Moultonborough Inn

3 out of 5
Save 100% on your flight
Price was $897, price is now $635 per person
$635
per person
Jul 23 - Jul 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
Price was $3,607, price is now $2,555 per person
$2,555
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $2,036, price is now $1,452 per person
$1,452
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

Top places to visit in Middlesex County

Hudson historic town center aerial view including Unitarian Church Marlborough and Town Hall on Main Street in town of Hudson, Massachusetts MA, USA.
FlightsFlightsHotelsHotels

Marlborough

Marlborough

Flight deals to Middlesex County

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

Wed, Sep 9 - Thu, Sep 10
LAX
Los Angeles
BOS
Boston
$232 Roundtrip, found 3 days ago
$232
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Sep 9 from Los Angeles to Boston, returning Thu, Sep 10, priced at $232 found 3 days ago
Tue, Sep 29 - Fri, Oct 2
PDX
Portland
BOS
Boston
$282 Roundtrip, found 1 day ago
$282
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 29 from Portland to Boston, returning Fri, Oct 2, priced at $282 found 1 day ago
Fri, Aug 21 - Sat, Aug 22
LAX
Los Angeles
PVD
Providence
$292 Roundtrip, found 3 days ago
$292
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 21 from Los Angeles to Providence, returning Sat, Aug 22, priced at $292 found 3 days ago

Top rated hotels for your Middlesex County vacation

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
1.46 mi from city center
$176 nightly
The price is $204 total per night
$204 total
Jun 7 - Jun 8
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.
Pet friendly
Free WiFi
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
$275 nightly
The price is $308 total per night
$308 total
Jun 30 - Jul 1
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.
Spa
Parking included
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
$169 nightly
The price is $189 total per night
$189 total
Jun 7 - Jun 8
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
Don't see what you're looking for?
See all available properties in Middlesex County
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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.