29 Best Tiny Houses for Rent in Woodbury, CT | Peerspace

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Popular tiny houses

Middlebury Countryside With Elegant Light-Filled Home and Breathtaking Scenic Outlook

20 guests

From

$190

/hr

2 hr min

Center of rural town

20 guests

From

$100

/hr

3 hr min

Beautiful 6 bedroom home in country setting only 90 minutes from NYC.

75 guests

From

$195

/hr

4 hr min

charming, cozy two-story house near Candlewood lake

30 guests

From

$150

/hr

5 hr min

Architectural Mid Century Modern Lakefront Property

Lakeside Woods, Sherman, CT

30 guests

From

$850

/hr

5 hr min

Lake House with Natural Light + Multiple Shoot Spaces

18 guests

From

$100

/hr

3 hr min

70's Time Capsule! Unique Mid-Century Full House/Private

5.0 (13)

150 guests

From

$145

/hr

4 hr min

Cozy modern one acre home with loft style livingroom

125 guests

From

$600

/hr

10 hr min

Suburban luxury townhome, walking distance to lake

25 guests

From

$500

/hr

4 hr min

Cozy and Beautiful Retreat Getaway Basement Apartment

9 guests

From

$150

/hr

4 hr min

Downtown Studio with Hardwood Floors + High Ceilings

5.0 (2)

15 guests

From

$80

/hr

4 hr min

Enchanted First Period Country Estate Surrounded by Lakes & Great White Pines

30 guests

From

$180

/hr

2 hr min

Stylish, modern country house in Dutchess County idyllic setting. Owned by Director of Design, thoughtfully curated!

15 guests

From

$300

/hr

2 hr min

Luxury French Colonial Home with Picturesque Lake Views

30 guests

From

$500

/hr

4 hr min

Historic Country Farmhouse on 13 Acres

14 guests

From

$400

/hr

2 hr min

Midcentury home w/ pool + tennis court in Hudson Valley

5.0 (1)

15 guests

From

$150

/hr

3 hr min

Cool, Quirky Historic House Built in 1719 on 11 Acres

40 guests

From

$150

/hr

1 hr min

Private Multi-Use Event & Meeting Space – Parking for 20 | Quiet Neighborhood

5.0 (1)

50 guests

From

$75

/hr

3 hr min

Apartment in Artsy Westville New Haven.

Amity, New Haven, CT

5.0 (1)

20 guests

From

$65

/hr

3 hr min

Contemporary Cabin in the Woods

12 guests

From

$200

/hr

4 hr min

Sage Haven: Elegant, Comfortable, Close to Yale & Downtown New Haven

Prospect Hill Historic District, New Haven, CT

5.0 (1)

8 guests

From

$100

/hr

4 hr min

Starlight: Beautiful third floor apartment. Tons of natural light!

Prospect Hill Historic District, New Haven, CT

5.0 (2)

8 guests

From

$100

/hr

4 hr min

Modern Open-Concept Gem on 7 Private Acres with Camp Site + Forest

25 guests

From

$250

/hr

6 hr min

Loft style vibe with exposed brick in urban downtown area

Wooster Square, New Haven, CT

10 guests

From

$65

/hr

2 hr min

The Pearl, New Have

Fair Haven, New Haven, CT

5.0 (6)

6 guests

From

$130

/hr

4 hr min

Modern Luxury Home in Milford, CT – Perfect for Events & Productions

20 guests

From

$100

/hr

5 hr min

Coastal New England Historic Home

40 guests

From

$150

/hr

4 hr min

4 mins from Yale | 4BD | Fire Pit | Outdoor dining

West River, New Haven, CT

20 guests

From

$150

/hr

4 hr min

Light filled intimate studio just outside a busy upscale town

8 guests

From

$150

/hr

2 hr min

Similar searches in Woodbury, CT

Updated October 25, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.