Vacation rentals in Aspetuck River

The Cozy Little Cottage

Charming guest apartment on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.

Value · Location · Bathroom

Weston Escape, Fire Pit, Gym, Jacuzzi Tub

Welcome to your Weston retreat, a haven where time slows and memories bloom amid nature. Luxury hand-built furniture and original paintings wrap every room in tasteful creativity. Enjoy a coffee in the garden encircled gym, or sink into the jacuzzi tub under skylit stars, or circle the fire pit with marshmallows and family stories. Hike Devil’s Den or Aspetuck Trails in minutes; feed friendly goats nearby. Exclusive Westport dining, shops, and beaches are a short drive away, 90 minutes from NYC.

Location · Family · Kitchen

3‑Acre Weston Retreat w/ Pool & Basketball Court

Escape to an elegant 3-acre private retreat in Weston, CT, just minutes from Westport. Surrounded by nature, this spacious estate offers a heated pool (in season), full basketball court, gas fire pit, and a stunning double-height great room designed for effortless relaxation. Enjoy inviting spaces indoors and out, creating the perfect setting for a refined getaway with family and friends. Please note: This is a private residential property. No parties, events, gatherings, or unregistered guests.

Value · Family · Sleep quality

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

Location · Family · Condition

Garden Level 2 Bedroom Suite 5 Min to Westport

Welcome to your private garden-level retreat in Weston CT. An artfully designed, cozy, 2 bedroom suite. With its own entrance, secluded patio with wooded and peaceful surroundings, this curated space blends comfort, style, and serenity. Just minutes from Westport, it offers an award-winning mattresses, a cozy lounge area, organic coffee bar, high-speed WiFi, and more. Calm, clean, and thoughtfully designed. Guests describe it as peaceful, beautifully styled, and full of thoughtful touches.

Family · Location · Beach

Private Studio Apartment Kitchen Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)

Family · Location · Breakfast

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.

Location · Family · Solo travel

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Location · Value · Decor

Nama-stay: sweet Saugatuck Shores beach cottage

Escape to our beautifully curated pink beach cottage in the exclusive Saugatuck Shores neighborhood of Westport, Connecticut. Located on a scenic peninsula and just 150 steps from the water, this charming retreat offers the perfect blend of coastal relaxation and convenience. Watch spectacular sunrises over the water and end the day with breathtaking sunsets. Our neighborhood is ideal for walking, running, biking, paddle boarding, kayaking, and other water activities.

Location · Family · Outdoor spaces

Stareway to Heaven

Welcome to your ideal beachside retreat in Fairfield, CT. This fully furnished 4-bedroom, 3 1/2 bath home offers an open-concept living space, a chef’s kitchen, and a private rooftop deck with stunning coastal views. Just steps from the beach and close to downtown shops and dining, it provides the perfect blend of luxury and convenience. Optional beach cruiser rentals and paddleboards are available. Flexible rental terms are offered for both short- and long-term stays.

Family · Location · Nearby

Villa Après Sea

Get ready to play with the whole family at this stylish/private/gated 1-acre Gold Coast house equipped w/ a ping-pong table, fire-pit, grill, swing-set, yard games, & outdoor furniture. Grand great room is adorned w/ an 85” TV & a piano. Stocked kitchen & well-appointed dining room is an entertainer's delight. What vacay would be complete w/o a playroom decked w/ toys? Minutes to: 10: Downtown Westport 14: Compo Beach 15: FairfieldU 39: Yale 70: NYC

Location · Family · Indoor spaces

River Cottage in Weston, CT

Welcome to “River Cottage”, our enchanting private guest cottage in the picturesque town of Weston, CT, nestled on a riverfront property. Located about 45 miles from NYC, and 10 minutes from the lively town of Westport, our two-bedroom cottage is the ideal location for a relaxing few days, a business trip in the area or visiting family and friends. Perched near the tranquil Saugatuck River, the immediate area is a haven for hiking and trout fishing.

Location · Family · Decor