Easily book a unique space in Canaan, CT | Peerspace

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Canaan Event Spaces

From rooftop parties to private dining, explore event spaces in Canaan built for any occasion.

1740 Litchfield Luxury Farmhouse

5.0 (1)

12 guests

…3 fireplaces and a massive eat in kitchen with Viking appliances! 2 large outdoor dining

From

$799

/hr

2 hr min

Litchfield Estate: 1800s House, Cottage, Red Barn on a Pond

50 guests

A country place gathered around water, about two hours from Manhattan and twenty minutes

From

$500

/hr

8 hr min

Family farm with pasture views in the hills of the Berkshires

Great Barrington, HOUSATONIC, MA

50 guests

North Plain Farm sits just outside of Great Barrington, in the hills of the Berkshires.

From

$125

/hr

4 hr min

Chic Woodside Cottage in Hudson Valley Woods

Gallatin, Ancram, NY

15 guests

…is also ideal for brand activations, product shoots, creative pop-ups, and art

From

$175

/hr

4 hr min

Historic Lakeside Boutique Bar, Restaurant, & Event Space in Upstate NY

100 guests

…one flight up an antique staircase. The grassy outdoor space can suit anything from a

From

$920

/hr

5 hr min

Barns, country setting, pond and Turn of the century larg home

Stanford, Stanfordville, NY

60 guests

We have a large barn with indoor and outdoor arena and a large viewing room looking out

From

$300

/hr

1 hr min

Rustic and homey Pub nestled in a beautiful upstate New York village

Claverack, PHILMONT, NY

50 guests

My building was constructed in 1898. I am the 5th owner who purchased the property in

From

$150

/hr

4 hr min

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Canaan Creative Spaces

Find Canaan studios and creative spaces built for photo shoots, video production, content creation, and more.

Private & Charming Country House

12 guests

Set on a private 2-acre lot, this 2500sq house is perfect for photoshoots and video

From

$200

/hr

4 hr min

Historic Country Farmhouse on 13 Acres

14 guests

A beautifully restored 1790 Connecticut farmhouse on 14 completely private acres -

From

$400

/hr

2 hr min

Upstate NY Lakehouse with Incredible Sunset Views

Copake, Craryville, NY

10 guests

A unique and picturesque two-dwelling property on Copake Lake, offering stunning

From

$400

/hr

1 hr min

Contemporary Cabin in the Woods

12 guests

Small in size but big in design, this off-grid cabin is the perfect setting for

From

$200

/hr

4 hr min

Downtown Turn-of-Century Theater

Great Barrington, MA

5.0 (2)

20 guests

The theater marries the beauty, warmth and intimacy of a turn-of-the-century proscenium

From

$400

/hr

5 hr min

Pine cabin in Berkshire Mountains on 6 acres of woods with pond.

30 guests

Rustic-meets-modern, four bedroom cabin with kids bunk room and playroom, TV room,

From

$99

/hr

6 hr min

Active farm with pasture views in the Berkshire hills

Great Barrington, HOUSATONIC, MA

25 guests

North Plain Farm sits just outside of Great Barrington, in the hills of the Berkshires.

From

$100

/hr

5 hr min

Light Airy Glass Cabin | 5244

5.0 (1)

25 guests

Book our beautiful light airy glass cabin conveniently located in Hillsdale, New

From

$575

/hr

8 hr min

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Popular Activities

Featured activities in Canaan, CT

Updated February 19, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.