Holiday houses in Monroe

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Value · Family · Biking

Cozy, updated single family in Fairfield County

Welcome to your home away from home! Thoughtfully furnished with comfort, style, and convenience, this cozy retreat is perfectly situated for your next Fairfield County visit. Located just one minute from SHU and the Merritt Parkway, you're ideally placed to explore local parks, beaches, shopping, and delicious restaurants. Having personally enjoyed living here, we've crafted a welcoming space with special touches that we’re excited to share with you. Relax, settle in, and feel right at home!

Location · Value · Heating

Enchanting Guest Cottage

Your own cozy cottage nestled away in the most charming, historical part of Fairfield. Where the sounds of the babbling brook lull you to sleep and baby deer peek from behind the lush trees. Serene and enchanting, this 1940s bungalow is bursting with original details and warmth. A one minute drive to the most divine chocolatier, as well as fine dining at Bonda, all your snack needs at the Corner Market. Perfect for a quiet retreat when coming back to nature and beauty fills your soul.

Family · Location · Decor

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Value · Location · Pets

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm, a one bedroom, one bath cottage located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two. **Access to the 2nd floor bedroom is a steep and open staircase** (see interior photo listed under Laundry)

Value · Family · Walkability

Rustic farmhouse in the country, walk to village!

Charming 1830s country farmhouse in the heart of Sandy Hook village. This stylish home features original red oak floors and decorative brick fireplaces that add timeless character. Enjoy a walkable lifestyle with restaurants, coffee shops, bars, liquor stores, and everyday amenities just steps away. Rocky Glen State Park and a nearby Aquilla Nest and Mclaughlin vineyard offer scenic escapes just minutes from home. A perfect blend of historic charm and village convenience.

Value · Location · TV

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Family · Location · Accuracy

Serenity Haven: A Modern Retreat

Escape to a newly renovated private guest house in peaceful Monroe, CT. Set in a lush, tree-lined backyard with its own entrance and spacious deck, it’s an inviting retreat for families, business travelers, or a quiet getaway. Just steps away, explore the scenic, mostly flat Housatonic Valley Rail Trail for walking, jogging, and biking. Nearby Wolfe Park and Great Hollow Lake offer a seasonal sandy swimming beach, fishing, non-motorized boating, and picnic areas.

Family · Location · Hiking

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Location · Value · Walkability

Sunny Private Suite

Bright and private furnished 1-bedroom, 1-bath in-law apartment with separate entrance in Huntington section of Shelton. Features a sunny living area with sofa bed, full bath, and well-equipped kitchenette. Ideal for professionals or traveling nurses. Minutes to Shelton corporate offices and local businesses, and close to major hospitals. Located in a quiet residential setting with convenient access to shopping, dining, and major highways.

Location · Value · Getting around

Midcentury Lakeside Guest Suite

Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.

Value · Location · TV

Mid-Century Modern House - Ciela Haus

IG: @cielahaus A mid-century modern home with cathedral ceilings, carefully curated interiors and a warming indoor charcoal BBQ. It is the perfect getaway for a group of friends or family to explore the outdoors, farms, wineries or to simply enjoy tranquility. I hope you enjoy staying here as much as I loved renovating, curating and styling it!

Family · Value · Nearby