---
title: "South Shaftsbury Vacation Packages & Trips 2026 | Expedia"
description: "FREE cancellation on select hotels Bundle South Shaftsbury flight and hotel to build your own South Shaftsbury vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of South Shaftsbury holiday trips & travel deals."
canonical: "https://www.expedia.ca/South-Shaftsbury.d553248634999160873.Destination-Travel-Guides"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-13T11:06:59Z
---

# South Shaftsbury Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ## Plan, book, travel with confidence
- ### Better together
Save up to CA $4,200 when you book a flight and hotel together\*
- ### Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ### Rest easy
Plan, book, and manage your trip all in one place

#### Your South Shaftsbury Vacation

Enjoy unforgettable adventures when you reserve a vacation package to South Shaftsbury. Whether you're a history buff, foodie or just a traveler who loves experiencing new places, there's something for everyone in this exciting city. In the mood for a bit of sightseeing? A trip to South Shaftsbury wouldn't be complete without visiting [Lake Shaftsbury State Park](https://www.expedia.ca/Lake-Shaftsbury-State-Park-Shaftsbury.d553248621551385179.Vacation-Attraction), [Robert Frost Stone House Museum](https://www.expedia.ca/Robert-Frost-Stone-House-Museum-Shaftsbury.d6330804.Vacation-Attraction) and other major attractions. Whatever your travel plans or budget, organizing your ultimate tailored South Shaftsbury vacation is a cinch with Expedia.

## Discover the most popular places to visit in South Shaftsbury

### Robert Frost Stone House Museum

Rating: 9.0/10 (12 reviews)

You can spend time browsing the exhibits at Robert Frost Stone House Museum during your trip to South Shaftsbury. Discover the mountain views and coffeehouses in this relaxing area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6330804)

## South Shaftsbury Hotel Deals

### [New Englander Inn Bennington](https://www.expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information)

![A hotel reception area with a modern design, featuring a reception desk, seating area, and artwork on the walls.](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/d072eff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 220 Northside Drive, Bennington, VT, 05201, US
- Location: 4.8 km from South Shaftsbury
- Star rating: 2.5/5
- Guest rating: 7.6/10 (Good, 1000 reviews)
- Price: CA $115, CA $125 total, includes taxes & fees, Nov 15 - Nov 16

### [Hampton Inn Bennington](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information)

![A hotel room with two beds, a desk with a television, and a window with a mountain view.](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/c7a3db42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 51 Hannaford Square, Bennington, VT, 05201, US
- Location: 4.2 km from South Shaftsbury
- Star rating: 2.5/5
- Guest rating: 8.6/10 (Excellent, 1001 reviews)
- Price: CA $197, CA $215 total, includes taxes & fees, Nov 22 - Nov 23

### [Knotty Pine](https://www.expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information)

![A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/3d1e6eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 130 Northside Dr, Bennington, VT, 05201, US
- Location: 5 km from South Shaftsbury
- Star rating: 2.5/5
- Guest rating: 8/10 (Very good, 192 reviews)
- Price: CA $139, CA $151 total, includes taxes & fees, Nov 15 - Nov 16
- Review: Clean

### [Hotel Vervana, Trademark Collection by Wyndham](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information)

![A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/0d5e7c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 141 West Main Street, Bennington, VT, 05201, US
- Location: 6.9 km from South Shaftsbury
- Star rating: 2.5/5
- Guest rating: 8.2/10 (Very good, 1001 reviews)
- Price: CA $120, CA $131 total, includes taxes & fees, Nov 22 - Nov 23
- Review: staff was very helpful. room was good and comfortable. ice machine was in another building , but not too inconvenient. waffle machine was broken, a bit disappointing. but not horrible.

### [Bennington Motor Inn](https://www.expedia.ca/Bennington-Hotels-Bennington-Motor-Inn.h1522906.Hotel-Information)

![A hotel room with a bed, desk, chair, television, and a mirror.](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522906/eae9ebc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 143 West Main Street, Bennington, VT, 05201, US
- Location: 6.9 km from South Shaftsbury
- Star rating: 2/5
- Guest rating: 7.6/10 (Good, 512 reviews)
- Price: CA $107, CA $117 total, includes taxes & fees, Nov 15 - Nov 16

### [South Shire](https://www.expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information)

![A room with wooden paneling, a piano, a chair, and a door leading to another room.](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/2785b1e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 124 Elm St, Bennington, VT, 05201, US
- Location: 7.3 km from South Shaftsbury
- Star rating: 4/5
- Guest rating: 9/10 (Wonderful, 141 reviews)
- Price: CA $214, CA $249 total, includes taxes & fees, Nov 16 - Nov 17

### [The Four Chimneys Inn](https://www.expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information)

![A large, two-story house with a covered porch and multiple chimneys.](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/e72452e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 21 West Road, Bennington, VT, 05201, US
- Location: 6.9 km from South Shaftsbury
- Star rating: 4/5
- Guest rating: 9.6/10 (Exceptional, 291 reviews)
- Price: CA $319, CA $348 total, includes taxes & fees, Nov 23 - Nov 24
- Review: Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar

### [Starlight Inn](https://www.expedia.ca/Bennington-Hotels-Starlight-Inn.h1507889.Hotel-Information)

![A hotel room with a wooden headboard, a large bed with red bedding, two red armchairs, a small table, and a window with a view of greenery.](https://images.trvl-media.com/lodging/2000000/1510000/1507900/1507889/f803720c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 357 Us Route 7 S, Bennington, VT, 05201, US
- Location: 9 km from South Shaftsbury
- Star rating: 2/5
- Guest rating: 6.8/10 (235 reviews)
- Price: CA $141, CA $154 total, includes taxes & fees, Nov 17 - Nov 18
- Review: Very nice old school Vermont motor inn. Dated decor, but all clean and well maintained. Except the shower. The shower was clean, but even with only a few people in the motel getting consistent hot/cold water was difficult. Literally our only complaint. Very good location to downtown, too. Only about 4 1/2 miles from Bennington College if you are visiting.

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.

[See all properties in South Shaftsbury](https://www.expedia.ca/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=553248634999160873&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Frequently Asked Questions

### How much does a South Shaftsbury vacation package cost?

You'll find cheap prices on Expedia for your South Shaftsbury escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to South Shaftsbury costs.

### What are the cheapest months to go to South Shaftsbury?

January, February and March are the best times to look for cheap South Shaftsbury vacation packages. Travelling in quieter periods means you can typically find better prices on flights and accommodations.

### How many days is enough for South Shaftsbury?

With a well-organized schedule, you can easily hit the top South Shaftsbury attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, consider booking your South Shaftsbury vacation for longer.

### How to find the best South Shaftsbury package deals?

Finding a cheap South Shaftsbury package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly South Shaftsbury package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.

### Is it cheaper to book a South Shaftsbury vacation as a package?

An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your South Shaftsbury escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.

### When to book a vacation package to South Shaftsbury?

If you've got your South Shaftsbury vacation dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for travelling on a whim.

### How to plan a trip to South Shaftsbury?

1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit South Shaftsbury.
2. Plan your budget wisely: On top of the price of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to South Shaftsbury.
3. Decide how long to go for: Now that you're more familiar with South Shaftsbury, you can figure out the ideal length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored South Shaftsbury vacation package.

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.