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Main Street Vacations

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

Hotwire can help you find your travel bliss with Main Street 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 Main Street

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 Main Street 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 Main Street well.

Main Street Flight + Hotel packages

Top Hotel Deals

See all 3,352 Hotels in Main Street
Main Street Station by Wyndham Vacation Rentals

Main Street Station by Wyndham Vacation Rentals

505 S. Main Street, Breckenridge
4.0 out of 5.0

On the Blue River at the end of Breckenridge's Main Street, this hotel lies across from the Blue River Boardwalk, adjacent to Maggie Pond, and two blocks from ...

$269

$269
Water House on Main Street by Wyndham Vacation Rentals

Water House on Main Street by Wyndham Vacation Rentals

600 Columbine Road, Breckenridge
4.5 out of 5.0

Conveniently near skiing facilities, this Breckenridge condo resort is located in the mountains, within 3 mi (5 km) of Riverwalk Center and Breckenridge Ski ...

$389

$389
Park Avenue Lofts by Great Western Lodging

Park Avenue Lofts by Great Western Lodging

500 Park Avenue, Breckenridge
3.0 out of 5.0

Conveniently near skiing facilities, this Breckenridge condo resort is located in the mountains, within 3 mi (5 km) of Edwin Carter Museum and Breckenridge Ski ...

Chimney Ridge by Ski Village Resorts

Chimney Ridge by Ski Village Resorts

109 N. Main Street, Breckenridge
3.5 out of 5.0

Conveniently near skiing facilities, this Breckenridge condo building is located in the mountains, within 3 mi (5 km) of Edwin Carter Museum and Breckenridge ...

Cimarron by Ski Village Resorts

Cimarron by Ski Village Resorts

305 South Park Avenue, Breckenridge
3.5 out of 5.0

Conveniently near skiing facilities, this Breckenridge condo building is within 3 mi (5 km) of Edwin Carter Museum and Breckenridge Ski Resort and close to winter ...

Los Pinos by Ski Village Resorts

Los Pinos by Ski Village Resorts

43 Snowflake Drive, Breckenridge
3.5 out of 5.0

Conveniently near skiing facilities, this Breckenridge condo building is located in the mountains, within 3 mi (5 km) of Edwin Carter Museum and Breckenridge ...

Main Street Retreat - Gondola to Lifts by RedAwning

Main Street Retreat - Gondola to Lifts by RedAwning

302 North Main Street, Breckenridge
4.0 out of 5.0

Situated in Breckenridge, this condo building is close to Edwin Carter Museum, Breckenridge Ski Resort, and Barney Ford House Museum. Also nearby are Riverwalk ...

Trails End Condominiums by Great Western Lodging

Trails End Condominiums by Great Western Lodging

455 Village Road, Breckenridge
3.5 out of 5.0

Located in the mountains, this Breckenridge condo resort offers ski-in/ski-out access within 3 mi (5 km) of Edwin Carter Museum and Breckenridge Ski Resort and ...

Sawmill Creek Condominiums by Great Western Lodging

Sawmill Creek Condominiums by Great Western Lodging

105 South Park Avenue, Breckenridge
3.5 out of 5.0

Located in the mountains, this Breckenridge condo building offers ski-in/ski-out access within 3 mi (5 km) of Edwin Carter Museum and Breckenridge Ski Resort ...

Sawmill Creek Condos

Sawmill Creek Condos

105 South Park Avenue,, BRECKENRIDGE

Situated in Breckenridge, this hotel is close to Edwin Carter Museum, Breckenridge Ski Resort, and Barney Ford House Museum. Also nearby are Riverwalk Center ...

Top Flight Deals

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