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Winchendon

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Winchendon Flights as Low as $274

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

American Airlines
Thu, Jul 16 - Tue, Jul 21
JAX
Jacksonville Intl.
ORH
Worcester Regional
$274 Roundtrip, found 11 hours ago
$274
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Jul 16 from Jacksonville Intl. to Worcester Regional, returning Tue, Jul 21, priced at $274 found 11 hours ago
American Airlines
Thu, Jul 16 - Tue, Jul 21
JAX
Jacksonville Intl.
ORH
Worcester Regional
$278 Roundtrip, found 11 hours ago
$278
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Jul 16 from Jacksonville Intl. to Worcester Regional, returning Tue, Jul 21, priced at $278 found 11 hours ago
Delta
Tue, Sep 1 - Tue, Sep 15
TPA
Tampa Intl.
ORH
Worcester Regional
$287 Roundtrip, found 12 hours ago
$287
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Tue, Sep 15, priced at $287 found 12 hours ago
Delta
Tue, Sep 1 - Mon, Sep 14
TPA
Tampa Intl.
ORH
Worcester Regional
$291 Roundtrip, found 2 days ago
$291
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Mon, Sep 14, priced at $291 found 2 days ago
Delta
Mon, Aug 31 - Mon, Sep 14
TPA
Tampa Intl.
ORH
Worcester Regional
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 31 from Tampa Intl. to Worcester Regional, returning Mon, Sep 14, priced at $292 found 2 days ago
JetBlue Airways
Tue, Sep 1 - Tue, Sep 15
TPA
Tampa Intl.
ORH
Worcester Regional
$311 Roundtrip, found 12 hours ago
$311
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Tue, Sep 15, priced at $311 found 12 hours ago
American Airlines
Thu, Jul 16 - Tue, Jul 21
JAX
Jacksonville Intl.
ORH
Worcester Regional
$315 Roundtrip, found 11 hours ago
$315
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Jul 16 from Jacksonville Intl. to Worcester Regional, returning Tue, Jul 21, priced at $315 found 11 hours ago
Delta
Thu, Sep 3 - Tue, Sep 15
TPA
Tampa Intl.
ORH
Worcester Regional
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 3 from Tampa Intl. to Worcester Regional, returning Tue, Sep 15, priced at $317 found 2 days ago
Delta
Tue, Sep 1 - Sun, Sep 13
TPA
Tampa Intl.
ORH
Worcester Regional
$321 Roundtrip, found 2 days ago
$321
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Sun, Sep 13, priced at $321 found 2 days ago
Delta
Mon, Aug 31 - Sun, Sep 13
TPA
Tampa Intl.
ORH
Worcester Regional
$322 Roundtrip, found 2 days ago
$322
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 31 from Tampa Intl. to Worcester Regional, returning Sun, Sep 13, priced at $322 found 2 days ago
American Airlines
Sun, Jul 19 - Mon, Jul 20
JAX
Jacksonville Intl.
ORH
Worcester Regional
$326 Roundtrip, found 10 hours ago
$326
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sun, Jul 19 from Jacksonville Intl. to Worcester Regional, returning Mon, Jul 20, priced at $326 found 10 hours ago
American Airlines
Thu, Jul 16 - Tue, Jul 21
JAX
Jacksonville Intl.
ORH
Worcester Regional
$326 Roundtrip, found 11 hours ago
$326
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Jul 16 from Jacksonville Intl. to Worcester Regional, returning Tue, Jul 21, priced at $326 found 11 hours ago
American Airlines
Tue, Sep 1 - Tue, Sep 15
TPA
Tampa Intl.
ORH
Worcester Regional
$332 Roundtrip, found 12 hours ago
$332
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Tue, Sep 15, priced at $332 found 12 hours ago
Delta
Tue, Sep 1 - Tue, Sep 15
TPA
Tampa Intl.
ORH
Worcester Regional
$337 Roundtrip, found 12 hours ago
$337
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Sep 1 from Tampa Intl. to Worcester Regional, returning Tue, Sep 15, priced at $337 found 12 hours ago
American Airlines
Sat, Aug 1 - Mon, Aug 10
JFK
John F. Kennedy Intl.
ORH
Worcester Regional
$360 Roundtrip, found 14 hours ago
$360
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Aug 1 from John F. Kennedy Intl. to Worcester Regional, returning Mon, Aug 10, priced at $360 found 14 hours ago
JetBlue Airways
Sat, Aug 1 - Mon, Aug 10
JFK
John F. Kennedy Intl.
ORH
Worcester Regional
$408 Roundtrip, found 14 hours ago
$408
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Sat, Aug 1 from John F. Kennedy Intl. to Worcester Regional, returning Mon, Aug 10, priced at $408 found 14 hours ago

Cheap Flights to Winchendon

Fall in love at first flight with your vacation to Winchendon by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winchendon on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winchendon, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winchendon

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchendon with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ORH airport.

What is the cheapest month to fly to Winchendon?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winchendon are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchendon?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winchendon.

What airport is best to fly into Winchendon?

When you’re planning your trip to Winchendon, convenience is the name of the game. Luckily, Winchendon Nashua Municipal Airport is nearby so you can deplane and get going on checking off everything on your Winchendon must-do list.

How much are flights to Winchendon?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchendon on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $274, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winchendon?

The trick to saving a stack of cash on your flight to Winchendon? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $274 right now, why wait?

Winchendon Flight Information
Destination airport
Worcester Regional
Destination airport IATA code
ORH
Roundtrip price
$274

Last Minute Hotel Deals in Winchendon

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Book a stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,011 reviews)
"It was frustrating trying to use the Wolf Pass. Everytime we went to line up for an attraction at the indoor adventure area, we had to get out of line to get someone at a register to print a receipt so we could use the pass, which was inconvenient and time consuming"

Reviewed on Jun 29, 2026

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Great Wolf Lodge Boston / Fitchburg, MA
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,004 reviews)
"For people visiting in the Gardner area, the Colonial is the perfect location! The front desk staff are so welcoming and attentive."

Reviewed on Jun 27, 2026

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The Colonial Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,007 reviews)
"It was clean staff was nice friendly and dressed in uniforms breakfast nice breakfast area was clean i would stay at ascend collection hotel again.. i wish would have done so near bar harbor area but didnt"

Reviewed on Jun 29, 2026

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Keene Elm City Hotel, an Ascend Collection Hotel
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

4 out of 5
99 Erdman Way Leominster MA
Book a stay at this business-friendly hotel in Leominster. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,002 reviews)
"Good, standard hotel. Nice staff."

Reviewed on Jun 29, 2026

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Doubletree by Hilton Hotel Leominster
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,006 reviews)
"Room had duct tape on the floor holding the carpet down, bathroom door had holes in it where hooks use to be, room was damp and musty, chair was in disrepair, call from front desk at 11pm stating smoking was occuring in the room (malfunctioning fire protection equipment), outlets intermittently ..."

Reviewed on Jun 28, 2026

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Best Western Plus Keene Hotel
Motel 6 Leominster, MA

Motel 6 Leominster, MA

2 out of 5
48 Commercial Rd Leominster MA
Stay at this motel in Leominster. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (1,002 reviews)
"Typical Motel setting. Lots of long term residents. This means that doors are open, people are smoking outside the rooms, camp chairs outside of rooms and lots of people activity (changing clothes in the parking lot, socializing etc). The room itself was poor. The bathroom door wouldn't close due ..."

Reviewed on Jun 29, 2026

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Motel 6 Leominster, MA
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
7.2/10 Good! (27 reviews)
"Unfortunately the room we booked (Kingsize Bed) had no place to hang any clothing!!🤔🤔🤔. No clothing rack!!!"

Reviewed on Jun 29, 2026

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Gardner Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (1,003 reviews)
"We stayed that this hotel for a last minute sports competition. The hotel was terribly outdated. The room seamed not very clean (dust in corners), with old worn linens (which did seem clean/ washed). The hallway smelled musty and the carpet was outdated and worn. In some places where the carpet had ..."

Reviewed on Jun 29, 2026

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Days Inn by Wyndham Keene NH
See all 232 properties in Winchendon
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.