Cheap Vacations in Middlesex County

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Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $536, price is now $416 per person
$416
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,023, price is now $1,377 per person
$1,377
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $1,447, price is now $1,011 per person
$1,011
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Deerfield Inn

Deerfield Inn

3 out of 5
Price was $875, price is now $629 per person
$629
per person
Sep 3 - Sep 7
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was $934, price is now $674 per person
$674
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was $1,128, price is now $822 per person
$822
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Hotel Providence

Hotel Providence

4 out of 5
Downtown Providence
Save 100% on your flight
Price was $1,389, price is now $1,036 per person
$1,036
per person
Sep 5 - Sep 12
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Providence (PVD)
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was $576, price is now $438 per person
$438
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Burlington Town Center
Price was $867, price is now $668 per person
$668
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Blue Water Resort

Blue Water Resort

3 out of 5
Bass River
Save 100% on your flight
Price was $1,800, price is now $1,396 per person
$1,396
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)

3-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $536, price is now $416 per person
$416
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $2,023, price is now $1,377 per person
$1,377
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $1,447, price is now $1,011 per person
$1,011
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,284, price is now $905 per person
$905
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was $934, price is now $674 per person
$674
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Good Hotels Boston

Good Hotels Boston

2 out of 5
Save 100% on your flight
Price was $1,205, price is now $885 per person
$885
per person
Sep 11 - Sep 14
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $609, price is now $459 per person
$459
per person
Sep 2 - Sep 5
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was $1,962, price is now $1,490 per person
$1,490
per person
Sep 2 - Sep 5
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was $576, price is now $438 per person
$438
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

3.5 out of 5
Price was $996, price is now $774 per person
$774
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
Price was $827, price is now $647 per person
$647
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $1,944, price is now $1,537 per person
$1,537
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)

4-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Price was $666, price is now $539 per person
$539
per person
Sep 3 - Sep 7
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Deerfield Inn

Deerfield Inn

3 out of 5
Price was $875, price is now $629 per person
$629
per person
Sep 3 - Sep 7
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $2,633, price is now $2,022 per person
$2,022
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Price was $1,302, price is now $1,032 per person
$1,032
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)
Luxury 2BR near Cambridge

Luxury 2BR near Cambridge

3 out of 5
Price was $1,365, price is now $1,107 per person
$1,107
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Boston (BOS)
Hyatus Designer Residences Somerville

Hyatus Designer Residences Somerville

4.5 out of 5
Price was $1,712, price is now $1,401 per person
$1,401
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was $1,306, price is now $1,071 per person
$1,071
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $2,769, price is now $2,277 per person
$2,277
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Price was $812, price is now $669 per person
$669
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Boston (BOS)
New Bedford Harbor Hotel

New Bedford Harbor Hotel

3 out of 5
Price was $692, price is now $571 per person
$571
per person
Sep 3 - Sep 7
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was $1,521, price is now $1,256 per person
$1,256
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)
The Charles Hotel

The Charles Hotel

5 out of 5
Price was $1,542, price is now $1,282 per person
$1,282
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Boston (BOS)

5-night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
The Inn on Arsenal

The Inn on Arsenal

2.5 out of 5
Price was $772, price is now $614 per person
$614
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,683, price is now $1,708 per person
$1,708
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) 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 $1,540, price is now $1,070 per person
$1,070
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Price was $1,128, price is now $822 per person
$822
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Save 100% on your flight
Price was $2,632, price is now $1,972 per person
$1,972
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was $1,258, price is now $952 per person
$952
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was $2,940, price is now $2,227 per person
$2,227
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Boston Marriott Burlington

Boston Marriott Burlington

4 out of 5
Price was $867, price is now $668 per person
$668
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Blue Water Resort

Blue Water Resort

3 out of 5
Save 100% on your flight
Price was $1,800, price is now $1,396 per person
$1,396
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
The Inn at Longwood Medical

The Inn at Longwood Medical

3.5 out of 5
Price was $1,203, price is now $934 per person
$934
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
Riviera Beach Resort

Riviera Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,704, price is now $1,326 per person
$1,326
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
The Boston Hotel

The Boston Hotel

2 out of 5
Price was $884, price is now $702 per person
$702
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)

6-7 night Middlesex County vacations

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham North Dartmouth / Fall River

Baymont by Wyndham North Dartmouth / Fall River

2.5 out of 5
Price was $640, price is now $491 per person
$491
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Hotel Providence

Hotel Providence

4 out of 5
Save 100% on your flight
Price was $1,389, price is now $1,036 per person
$1,036
per person
Sep 5 - Sep 12
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Providence (PVD)
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 $6,268, price is now $3,699 per person
$3,699
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
New Bedford Harbor Hotel

New Bedford Harbor Hotel

3 out of 5
Save 100% on your flight
Price was $830, price is now $593 per person
$593
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
The Coonamessett

The Coonamessett

3.5 out of 5
Save 100% on your flight
Price was $1,939, price is now $1,435 per person
$1,435
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,536 per person
$1,536
per person
Aug 31 - Sep 5
found 10 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Boston (BOS)
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
Save 100% on your flight
Price was $1,217, price is now $922 per person
$922
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Bourne Bridge Inn 

Bourne Bridge Inn 

2 out of 5
Price was $688, price is now $523 per person
$523
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Red Roof Inn & Suites Newport – Middletown, RI

Red Roof Inn & Suites Newport – Middletown, RI

2 out of 5
Save 100% on your flight
Price was $906, price is now $694 per person
$694
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Providence (PVD)
InnSeason Resorts HarborWalk

InnSeason Resorts HarborWalk

2.5 out of 5
Save 100% on your flight
Price was $1,274, price is now $976 per person
$976
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Hampton Inn & Suites Plymouth

Hampton Inn & Suites Plymouth

2.5 out of 5
Save 100% on your flight
Price was $1,090, price is now $846 per person
$846
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $3,193, price is now $2,484 per person
$2,484
per person
Aug 18 - Aug 23
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) 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.

Tue, Aug 25 - Mon, Aug 31
LAX
Los Angeles
BOS
Boston
$246 Roundtrip, found 16 hours ago
$246
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Los Angeles to Boston, returning Mon, Aug 31, priced at $246 found 16 hours ago
Wed, Sep 30 - Tue, Oct 6
LAX
Los Angeles
BOS
Boston
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 30 from Los Angeles to Boston, returning Tue, Oct 6, priced at $247 found 3 days ago
Tue, Sep 22 - Wed, Oct 7
LAX
Los Angeles
BOS
Boston
$247 Roundtrip, found 19 hours ago
$247
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Tue, Sep 22 from Los Angeles to Boston, returning Wed, Oct 7, priced at $247 found 19 hours 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
$164 nightly
The price is $190 total per night
$190 total
Aug 16 - Aug 17
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.
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
Aug 10 - Aug 11
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
$137 nightly
The price is $153 total per night
$153 total
Aug 13 - Aug 14
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.
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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.