Cheap Vacations in Cumberland County

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Cumberland 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)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,082, price is now $722 per person
$722
per person
Sep 4 - Sep 7
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
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 21 hours 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 11 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 21 hours ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
Price was $1,196, price is now $877 per person
$877
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,139, price is now $1,602 per person
$1,602
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
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 21 hours 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)

3-night Cumberland 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)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,082, price is now $722 per person
$722
per person
Sep 4 - Sep 7
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
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 21 hours 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 21 hours 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 6 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 11 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 11 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 21 hours 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 21 hours 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 21 hours ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)

4-night Cumberland 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 $632, price is now $529 per person
$529
per person
Sep 3 - Sep 7
found 11 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 11 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
Price was $1,196, price is now $877 per person
$877
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $2,139, price is now $1,602 per person
$1,602
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
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 11 hours ago
Roundtrip flight included
Orlando (MCO) 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 11 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Cambridge Common House

Cambridge Common House

4 out of 5
Price was $1,101, price is now $915 per person
$915
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $2,967, price is now $2,487 per person
$2,487
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Price was $714, price is now $604 per person
$604
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,511, price is now $1,288 per person
$1,288
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $700, price is now $606 per person
$606
per person
Sep 3 - Sep 7
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
Price was $832, price is now $723 per person
$723
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)

5-night Cumberland 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)
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $3,005, price is now $2,014 per person
$2,014
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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)
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)
The Langham, Boston

The Langham, Boston

5 out of 5
Price was $2,442, price is now $1,961 per person
$1,961
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Howard Johnson by Wyndham Quincy/Boston

Howard Johnson by Wyndham Quincy/Boston

2 out of 5
Price was $784, price is now $647 per person
$647
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Price was $1,248, price is now $1,030 per person
$1,030
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
The Verb Hotel

The Verb Hotel

3.5 out of 5
Price was $1,127, price is now $940 per person
$940
per person
Aug 26 - Aug 31
found 15 hours ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)
Lakeside Inn

Lakeside Inn

2 out of 5
Price was $749, price is now $630 per person
$630
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Price was $1,754, price is now $1,477 per person
$1,477
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

3 out of 5
Price was $738, price is now $629 per person
$629
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Cambria Hotel Boston Downtown - Seaport

Cambria Hotel Boston Downtown - Seaport

3.5 out of 5
Price was $940, price is now $804 per person
$804
per person
Aug 26 - Aug 31
found 15 hours ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Boston (BOS)

6-7 night Cumberland 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)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $2,571, price is now $1,873 per person
$1,873
per person
Aug 17 - Aug 24
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
All Seasons Inn & Suites Smithfield Providence

All Seasons Inn & Suites Smithfield Providence

3 out of 5
Price was $735, price is now $583 per person
$583
per person
Sep 9 - Sep 15
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Holiday Inn Boston - Dedham Hotel & Conference Center by IHG

Holiday Inn Boston - Dedham Hotel & Conference Center by IHG

3 out of 5
Price was $890, price is now $719 per person
$719
per person
Sep 9 - Sep 15
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
HomeAwhile

HomeAwhile

2 out of 5
Price was $1,247, price is now $1,047 per person
$1,047
per person
Aug 17 - Aug 24
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
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)
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)
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)

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.

Fri, Sep 25 - Mon, Sep 28
EWR
New York
PWM
Portland
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select United flight, departing Fri, Sep 25 from New York to Portland, returning Mon, Sep 28, priced at $181 found 2 days ago
Tue, Sep 29 - Sat, Oct 3
RDU
Raleigh
PWM
Portland
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 29 from Raleigh to Portland, returning Sat, Oct 3, priced at $189 found 2 days ago
Sun, Sep 13 - Tue, Sep 15
JFK
New York
PWM
Portland
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Sep 13 from New York to Portland, returning Tue, Sep 15, priced at $207 found 5 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
1.79 mi from city center
$144 nightly
The price is $159 total per night
$159 total
Jul 27 - Jul 28
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
$151 nightly
The price is $167 total per night
$167 total
Jul 26 - Jul 27
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
0.4 mi from city center
$433 nightly
The price is $480 total per night
$480 total
Jul 19 - Jul 20
Total with taxes and fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, just a 3-minute walk from Cross Insurance Arena and 8 minutes by foot from Casco Bay Lines Ferry Terminal.
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.