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Windsor Vacations

Pack those stellar shades. We have Windsor 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 Windsor – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Windsor 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 Windsor

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 Windsor 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 Windsor well.

Top Hotel Deals

See all 639 Hotels in Windsor
Windsor Mansion Inn

Windsor Mansion Inn

153 Pembroke Road, Windsor
4.0 out of 5.0

Situated in Windsor, this bed & breakfast is within 2 mi (3 km) of Old Constitution House, South Congregational Church, and American Precision Museum. Cornish-Windsor ...

Snapdragon Inn

Snapdragon Inn

26 Main Street, Windsor
4.0 out of 5.0

Situated in Windsor, this bed & breakfast is within a 10-minute walk of Old Constitution House and South Congregational Church. American Precision Museum and ...

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
3.0 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 ...

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

2940 State Route 103, Proctorsville
4.0 out of 5.0

Situated in a rural location, this spa hotel is within 9 mi (15 km) of Dorsey Park, Okemo Mountain Resort, and Buttermilk Falls. Camp Plymouth State Park is ...

$116

$116
Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green, Woodstock
4.0 out of 5.0

Situated in Woodstock, this resort is within a 5-minute walk of Woodstock Town Hall Theatre and Dana House Museum. Billings Park and Trail and Mount Tom Peak ...

$249

$249
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 ...

$399

$399
Killington Mountain Lodge

Killington Mountain Lodge

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 ...

$154

$154
Holiday Inn Express Hotel & Suites White River Junction

Holiday Inn Express Hotel & Suites White River Junction

121 Ballardvale Dr, White River Junction
3.0 out of 5.0

Situated in White River Junction, this hotel is within 2 mi (3 km) of Upper Valley Aquatic Center, Briggs Opera House, and Main Street Museum. New England Transportation ...

$101

$101
Six South St Hotel

Six South St Hotel

6 South Street, Hanover
3.0 out of 5.0

Situated in Hanover, this hotel is within a 10-minute walk of Hopkins Center for the Arts, Hood Museum of Art, and Dartmouth College. Baker-Berry Library and ...

$154

$154

Top Flight Deals

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