Cheap Vacations in Cumberland County

Choose two or more items and save on your trip:

Cumberland 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)
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)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,403, price is now $981 per person
$981
per person
Jul 16 - Jul 19
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
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)
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)
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)
Furnished Apartment near BMC

Furnished Apartment near BMC

3 out of 5
South End
Save 100% on your flight
Price was $1,875, price is now $1,406 per person
$1,406
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
Save 100% on your flight
Price was $1,742, price is now $1,319 per person
$1,319
per person
Jul 15 - Jul 22
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Augusta (AUG)
The Coonamessett

The Coonamessett

3.5 out of 5
Save 100% on your flight
Price was $3,101, price is now $2,352 per person
$2,352
per person
Jul 13 - 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
Back Bay
Price was $1,335, price is now $1,014 per person
$1,014
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

3-night Cumberland 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)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,403, price is now $981 per person
$981
per person
Jul 16 - Jul 19
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
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)

4-night Cumberland 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)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,730, price is now $1,374 per person
$1,374
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

5-night Cumberland 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 Cumberland County vacations

Price found within the past 48 hours. Click for updated prices.
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)
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 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)
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)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Save 100% on your flight
Price was $2,083, price is now $1,495 per person
$1,495
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Save 100% on your flight
Price was $2,658, price is now $1,912 per person
$1,912
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

Top places to visit in Cumberland County

FlightsFlightsHotelsHotels

Portland

Portland

Flight deals to Cumberland County

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

Sun, Jul 19 - Fri, Jul 24
JFK
New York
PWM
Portland
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jul 19 from New York to Portland, returning Fri, Jul 24, priced at $181 found 1 day ago
Sun, Jul 19 - Fri, Jul 24
LGA
New York
PWM
Portland
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jul 19 from New York to Portland, returning Fri, Jul 24, priced at $212 found 1 day ago
Sat, Sep 12 - Tue, Sep 15
PHL
Philadelphia
PWM
Portland
$232 Roundtrip, found 4 hours ago
$232
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Sat, Sep 12 from Philadelphia to Portland, returning Tue, Sep 15, priced at $232 found 4 hours ago

Top rated hotels for your Cumberland County vacation

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
1.79 mi from city center
$118 nightly
The price is $131 total per night
$131 total
Jun 10 - Jun 11
Total with taxes and fees
With a stay at Clarion Hotel Portland Airport ME in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Pool
Hot Tub
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
0.4 mi from city center
$313 nightly
The price is $346 total per night
$346 total
Jun 7 - Jun 8
Total with taxes and fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 5-minute drive of State Theatre and Maine Medical Center.
Pet friendly
Free WiFi
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
0.3 mi from city center
$287 nightly
The price is $318 total per night
$318 total
Jun 15 - Jun 16
Total with taxes and fees
With a stay at Cambria Hotel Portland Downtown-Old Port in Portland (Downtown Portland), you'll be within a 5-minute drive of State Theatre and Maine Medical Center.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Cumberland County
View all properties
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.