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A lake with a tree in the foreground, a forested shoreline, and distant mountains under a partly cloudy sky.

Fair Haven Vacations from $904

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The Latest Fair Haven Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 7 - Oct 10

    Holiday Inn Club Vacations Mount Ascutney Resort by IHG + Flight

    Brownsville
    3 nights
    3.0 star property
    9.0/10 - Wonderful (862 reviews)
    Roundtrip • New York (EWR) - Rutland (RUT)
    EWR - RUT • 1 stop RUT - EWR • 1 stop
    $1,074
    $904
    per traveler
    found 14 hours ago
    Holiday Inn Club Vacations Mount Ascutney Resort by IHG
  • Breakfast and dinner served
    Sep 8 - Sep 14

    The Mountain Inn at Killington + Flight

    Killington
    6 nights
    2.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "The carpet was filthy. Looked like it hadn't been vacuumed in weeks. The bedding was dirty - a brown spot and it was off putting."
    Reviewed July 31, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - RFD • 2 stops
    $1,296
    $1,087
    per traveler
    found 1 day ago
    The Mountain Inn at Killington
  • Lobby
    Sep 8 - Sep 14

    Days Inn by Wyndham Rutland/Killington Area + Flight

    Rutland
    6 nights
    2.5 star property
    6.8/10 - (1,001 reviews)
    "."
    Reviewed August 1, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - RFD • 2 stops
    $1,144
    $967
    per traveler
    found 1 day ago
    Days Inn by Wyndham Rutland/Killington Area
  • Lounge
    Sep 8 - Sep 14

    Greenbrier Inn + Flight

    Killington
    6 nights
    2.0 star property
    9.4/10 - Exceptional (685 reviews)
    "The hotel was very nice, quaint and clean. It is in a great location just prior to the entry of the access road. Large room. Small hotel with only about 20 rooms. Breakfast included. I would recommend a stay."
    Reviewed July 16, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - RFD • 2 stops
    $1,190
    $1,010
    per traveler
    found 1 day ago
    Greenbrier Inn
  • Front of property
    Sep 8 - Sep 14

    Ski in & out Spruce Glen Townhomes on Great Eastern Trail + Flight

    Killington
    6 nights
    3.0 star property
    9.0/10 - Wonderful (64 reviews)
    "Townhouse was clean and had comfortable beds, which are rare to find. Great for families and allows dogs. There is a nice front and back yard to walk the dogs on leash. Host, Ryan, was very attentive and gets back to you quickly with any questions or concerns. Close to restaurants (recommend the Look Out -best Brussels sprouts!, Sushi Yoshi and the Mad Hatter for ice cream. Close drive to Thundering Brook Falls a short walking distance (deck type path) to falls. Look forward to going back."
    Reviewed July 26, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - RFD • 2 stops
    $1,186
    $1,009
    per traveler
    found 1 day ago
    Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Discover the most popular places to visit in Fair Haven

Half Moon Pond State Park

Tucked within Bomoseen State Park, Half Moon Pond offers waterfront campsites and cozy cabins on a serene woodland lake. Rent a canoe to explore its calm waters or fish for largemouth bass from your cottage dock.

Fair Haven Hotel Deals

Interior detail

The Trailside Inn

The Trailside Inn
3.0 star property
23.4 mi from Fair Haven
9.2 out of 10, Wonderful, (156 reviews)
"Great room - very clean and comfortable. Helpful and welcoming staff - even left out breakfast for our early departure."
$151 nightly
The price is $166
Aug 3 - Aug 4
Total with taxes and fees
The Trailside Inn
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 Fair Haven

Frequently Asked Questions

How much does a Fair Haven vacation package cost?

You'll find cheap prices from $904 on Expedia for your Fair Haven escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Fair Haven costs.

What are the cheapest months to go to Fair Haven?

April, May and October are great times to search for cheap Fair Haven vacation packages. Opting to travel in quieter months means you can typically find reduced prices on accommodations and flights.

How many days is enough for Fair Haven?

The ideal length of your Fair Haven vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to hit all the top sights and discover some hidden gems along the way.

How to find the best Fair Haven package deals?

Begin your search for a Fair Haven package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Fair Haven package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Fair Haven adventure off to a flying start.

Is it cheaper to book a Fair Haven vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Fair Haven vacation by choosing your favorite type of stay, airline and car class.

When to book a vacation package to Fair Haven?

If you're considering an impromptu Fair Haven getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking well in advance.

Does Expedia offer Book Now, Pay Later Fair Haven vacation packages?

Your Fair Haven break is meant to be an escape from your busy life, not a source of money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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