Main Street Vacation Deals: Main Street, Castine Vacations

Main Street vacation package deals

Price found within the past 48 hours. Click for updated prices.

Captain Sweetser's Inn

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Rockland (RKD)

A garden, a fireplace in the lobby, and a communal living room are available at this bed & breakfast. Enjoy the free cooked-to-order breakfast each morning. A picnic area is also provided.

Glen Cove Inn & Suites

per person

Jul 17 - Jul 22

found 1 day ago

Roundtrip flight included

Louisville (SDF) to Rockland (RKD)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace and a garden are also provided.

Harborline Hotel

per person

Jun 20 - Jun 27

found 19 hours ago

Roundtrip flight included

Harrisburg (MDT) to Rockland (RKD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out, luggage storage, and laundry facilities are also on offer.

Trade Winds on the Bay

per person

Jul 17 - Jul 22

found 1 day ago

Roundtrip flight included

Louisville (SDF) to Rockland (RKD)

This aparthotel features an indoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and laundry facilities are also provided.

The Craignair Inn & Restaurant

per person

Jul 17 - Jul 22

found 1 day ago

Roundtrip flight included

Louisville (SDF) to Rockland (RKD)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Homeport Inn and Tavern

per person

Jun 14 - Jun 21

found 8 hours ago

Roundtrip non-stop flight included

Harrisburg (MDT) to Rockland (RKD)

A restaurant and a bar/lounge are featured at this inn. A terrace, a garden, and a library are also on offer.

Frequently asked questions

How much are vacation packages to Main Street?

Exciting adventures await you in Main Street, with Travelocity vacation packages from as low as $554. Including both flights and hotels, these incredible deals make it simple to explore more of our beautiful planet.

Where can I get the best vacation package deals for Main Street?

With around 400 air carriers and 1,000,000 hotels across the world, it’s tough to beat Travelocity. Look through our impressive range and create the perfect Main Street package deal. Isn’t it great when planning a trip is that easy?

Why should I book my Main Street vacation package with Travelocity?

Travel is all about making fantastic new memories and forgetting all your worries — which is why we provide you with a team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our huge range of vacation destinations. So what are you waiting for? There’s no time like the present to lock in the vacation of a lifetime.

Top Main Street hotel deals

Waterfront views steps from yacht club in idyllic Castine

This vacation home features laundry facilities.

Kitchen

Washer

Friendly home with our separate condos & free WiFi in the heart of downtown

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach

This condo features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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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.