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Pittsford Vacations

Pack those stellar shades. We have Pittsford vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Pittsford – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pittsford vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Pittsford

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Pittsford vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Pittsford well.

Top Hotel Deals

See all 394 Hotels in Pittsford
The Inn at Logan's Run

The Inn at Logan's Run

2636 US Route 7, Pittsford
4.0 out of 5.0

Situated in the mountains, this bed & breakfast is close to New England Maple Museum and Dorset Quarry. Area attractions also include Hathaway Farm and Rutland ...

Vermont Log Cabin Brandon by RedAwning

Vermont Log Cabin Brandon by RedAwning

82 Whistle Stop Ln, Pittsford
3.5 out of 5.0

Situated in Pittsford, this cabin is close to New England Maple Museum and Otter Valley Winery. Area attractions also include Brandon Museum and Neshobe River ...

Days Inn Rutland/Killington Area

Days Inn Rutland/Killington Area

401 Us Route 7 S, Rutland
3.0 out of 5.0

Situated in Rutland, this hotel is 0.9 mi (1.4 km) from Rutland Country Club and within 3 mi (5 km) of Hathaway Farm and Paramount Theater. Pine Hill Park and ...

$85

$85
Hillside Inn at Killington

Hillside Inn at Killington

375 Killington Rd, Killington
2.5 out of 5.0

Conveniently near skiing facilities, this Killington motel is located in the mountains, within 3 mi (5 km) of Gifford Woods State Park and Pico Mountain at Killington ...

$79

$79
Chalet Killington

Chalet Killington

2685 Killington Rd, Killington
2.5 out of 5.0

Conveniently near skiing facilities, this Killington hotel is within 3 mi (5 km) of Killington Golf Course and Killington Resort and close to winter sports such ...

Cortina Inn Hotel and Resort

Cortina Inn Hotel and Resort

103 US Route 4, Killington
3.5 out of 5.0

Situated in the mountains, this hotel is 2 mi (3.2 km) from Pico Mountain at Killington Ski Resort and within 6 mi (10 km) of Gifford Woods State Park and Norman ...

Mountain Green Ski & Golf Resort

Mountain Green Ski & Golf Resort

133 E Mountain Rd, Killington
3.5 out of 5.0

Located near the slopes, this Killington condo resort is in the mountains and within 1 mi (2 km) of Killington Golf Course, Killington Resort, and Killington ...

$289

$289
Middlebury Inn

Middlebury Inn

14 Court Square, Middlebury
3.0 out of 5.0

Located in the heart of Middlebury, this historic hotel is steps from Town Hall Theater and National Museum of the Morgan Horse. Henry Sheldon Museum of Vermont ...

$118

$118
Killington Mountain Lodge, BW Signature Collection

Killington Mountain Lodge, BW Signature Collection

2617 Killington Rd, Killington
4.0 out of 5.0

Conveniently near skiing facilities, this Killington hotel is located in the mountains, within 3 mi (5 km) of Killington Golf Course and Killington Resort, and ...

$139

$139
The Trailside Inn

The Trailside Inn

115 Coffee House Road, Killington
3.5 out of 5.0

Situated in Killington, this guesthouse is 1.6 mi (2.6 km) from Green Mountain National Golf Course and 2.4 mi (3.8 km) from Gifford Woods State Park. Killington ...

Top Flight Deals

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