Cheap Vacations in Cumberland County

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Cumberland County vacations

Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $1,286, price is now $946 per person
$946
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Coolidge Corner
Save 100% on your flight
Price was $1,488, price is now $1,039 per person
$1,039
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,554, price is now $1,089 per person
$1,089
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,954, price is now $1,391 per person
$1,391
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,867, price is now $1,334 per person
$1,334
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,317, price is now $953 per person
$953
per person
Oct 8 - Oct 12
found 16 hours ago
Roundtrip flight included
New Orleans (MSY) to Portland (PWM)
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,506, price is now $1,826 per person
$1,826
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Price was $1,512, price is now $1,127 per person
$1,127
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
The Cove at Rockport Hotel

The Cove at Rockport Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,399, price is now $1,795 per person
$1,795
per person
Oct 8 - Oct 12
found 16 hours ago
Roundtrip flight included
New Orleans (MSY) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,381, price is now $1,782 per person
$1,782
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)

3-night Cumberland County vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

3 out of 5
Price was $922, price is now $757 per person
$757
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,549, price is now $1,818 per person
$1,818
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was $1,234, price is now $965 per person
$965
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
Price was $1,370, price is now $1,072 per person
$1,072
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
The Hotel Marblehead

The Hotel Marblehead

3.5 out of 5
Save 100% on your flight
Price was $2,089, price is now $1,646 per person
$1,646
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

2.5 out of 5
Price was $1,163, price is now $923 per person
$923
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Price was $1,235, price is now $993 per person
$993
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Luxury 2BR near Cambridge

Luxury 2BR near Cambridge

3 out of 5
Price was $1,609, price is now $1,316 per person
$1,316
per person
Oct 8 - Oct 11
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
Hyatus Luxury Residences Salem

Hyatus Luxury Residences Salem

4.5 out of 5
Save 100% on your flight
Price was $3,388, price is now $2,794 per person
$2,794
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
The Rockport House

The Rockport House

2 out of 5
Price was $1,068, price is now $881 per person
$881
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Ginkgo House on Harvard

Ginkgo House on Harvard

3 out of 5
Price was $1,615, price is now $1,334 per person
$1,334
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New Orleans (MSY) to Boston (BOS)
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

3 out of 5
Price was $1,245, price is now $1,034 per person
$1,034
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)

4-night Cumberland 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
Save 100% on your flight
Price was $1,167, price is now $863 per person
$863
per person
Oct 27 - Oct 31
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,854, price is now $1,229 per person
$1,229
per person
Oct 22 - Oct 26
found 15 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,488, price is now $1,039 per person
$1,039
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,554, price is now $1,089 per person
$1,089
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $1,954, price is now $1,391 per person
$1,391
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $1,867, price is now $1,334 per person
$1,334
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,317, price is now $953 per person
$953
per person
Oct 8 - Oct 12
found 16 hours ago
Roundtrip flight included
New Orleans (MSY) to Portland (PWM)
The Newbury Boston

The Newbury Boston

5 out of 5
Save 100% on your flight
Price was $2,506, price is now $1,826 per person
$1,826
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Save 100% on your flight
Price was $1,286, price is now $946 per person
$946
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Price was $1,512, price is now $1,127 per person
$1,127
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
The Cove at Rockport Hotel

The Cove at Rockport Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,399, price is now $1,795 per person
$1,795
per person
Oct 8 - Oct 12
found 16 hours ago
Roundtrip flight included
New Orleans (MSY) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $2,381, price is now $1,782 per person
$1,782
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)

5-night Cumberland County vacations

Price found within the past 48 hours. Click for updated prices.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $982, price is now $792 per person
$792
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Portland (PWM)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $3,624, price is now $2,616 per person
$2,616
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Price was $1,782, price is now $1,372 per person
$1,372
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,201, price is now $1,702 per person
$1,702
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $2,509, price is now $1,942 per person
$1,942
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Price was $1,870, price is now $1,502 per person
$1,502
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $3,336, price is now $2,680 per person
$2,680
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,915, price is now $1,539 per person
$1,539
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Portland (PWM)
Canopy By Hilton Boston Downtown

Canopy By Hilton Boston Downtown

4 out of 5
Save 100% on your flight
Price was $2,768, price is now $2,224 per person
$2,224
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $1,935, price is now $1,582 per person
$1,582
per person
Oct 20 - Oct 25
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
HomeAwhile

HomeAwhile

2 out of 5
Price was $1,004, price is now $829 per person
$829
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,116, price is now $928 per person
$928
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Portland (PWM)

6-7 night Cumberland County vacations

Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,249, price is now $901 per person
$901
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,644, price is now $1,956 per person
$1,956
per person
Oct 1 - Oct 7
found 21 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
Save 100% on your flight
Price was $2,015, price is now $1,492 per person
$1,492
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $4,646, price is now $3,079 per person
$3,079
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $2,509, price is now $1,695 per person
$1,695
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,778, price is now $1,285 per person
$1,285
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $1,819, price is now $1,339 per person
$1,339
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $3,620, price is now $2,701 per person
$2,701
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Save 100% on your flight
Price was $1,875, price is now $1,422 per person
$1,422
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Save 100% on your flight
Price was $1,532, price is now $1,165 per person
$1,165
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Save 100% on your flight
Price was $2,494, price is now $1,922 per person
$1,922
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Boston (BOS)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Save 100% on your flight
Price was $1,722, price is now $1,344 per person
$1,344
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)

Top places to visit in Cumberland County

A lighthouse, a white house with a red roof, and rocky coastline at sunset.
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Portland

Portland

Flight deals to Cumberland County

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

Wed, Nov 11 - Wed, Nov 18
MCO
Orlando
PWM
Portland
$215 Roundtrip, found 5 days ago
$215
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando to Portland, returning Wed, Nov 18, priced at $215 found 5 days ago
Thu, Oct 22 - Sun, Oct 25
JFK
New York
PWM
Portland
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Oct 22 from New York to Portland, returning Sun, Oct 25, priced at $237 found 2 days ago
Mon, Oct 19 - Sat, Oct 24
LGA
New York
PWM
Portland
$237 Roundtrip, found 6 days ago
$237
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Oct 19 from New York to Portland, returning Sat, Oct 24, priced at $237 found 6 days 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
Reserve now, pay when you stay
1.79 mi from city center
$86 nightly
The price is $95 total per night
$95 total
Sep 8 - Sep 9
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.
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
3.85 mi from city center
$120 nightly
The price is $133 total per night
$133 total
Sep 2 - Sep 3
Total with taxes and fees
With a stay at Fireside Inn & Suites Portland in Portland (Nasons Corner), you'll be a 2-minute drive from Happy Wheels Skate Center and 7 minutes from Maine Mall.
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
$365 nightly
The price is $404 total per night
$404 total
Sep 8 - Sep 9
Total with taxes and fees
A stay at Portland Harbor Hotel places you in the heart of Portland, a short 3-minute walk from Cross Insurance Arena and within 5 minutes by car from Thompson's Point.
Pet friendly
Free WiFi
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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.