Cheap Vacations in Cumberland County

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Cumberland County vacations

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

Arcadian Hotel

3.5 out of 5
Coolidge Corner
Price was $1,055, price is now $744 per person
$744
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,650, price is now $1,536 per person
$1,536
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) 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)
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)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,726, price is now $1,242 per person
$1,242
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 15 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)
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)
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 22 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 15 hours ago
Roundtrip flight included
New Orleans (MSY) 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 19 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 11 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.
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Price was $1,055, price is now $744 per person
$744
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,650, price is now $1,536 per person
$1,536
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Huntsville (HSV) 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 14 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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)
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)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $1,726, price is now $1,242 per person
$1,242
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 15 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 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 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 22 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 15 hours ago
Roundtrip flight included
New Orleans (MSY) 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 15 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 20 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.
FlightsFlightsHotelsHotels

Portland

Portland

Flight deals to Cumberland County

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

Sat, Sep 12 - Tue, Sep 15
RDU
Raleigh
PWM
Portland
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Portland, returning Tue, Sep 15, priced at $210 found 6 days ago
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

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.
Pool
Hot Tub
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.
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.
Don't see what you're looking for?
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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.