House holiday rentals in Deep River

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Beauty and the Beach!

Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Shore Drive - 2 Bedroom/2 Bath/Bunk/Queen Oasis

Stay with us for a relaxing, family beach experience! This is a newly remodeled (2022) home with a spacious patio, seating w/table for 6 and large backyard. Walking distance to Waterford & Ocean Beach, Waterford Beach Park, Eugene O'Neill Theater and Harkness State Park. 15-20 min drive to Mystic, Stonington, Vineyards, 25 min to Mohegan Sun & Foxwoods. Close to the Lawrence + Memorial Hospital, Pfizer, GD (EB), CT College, Mitchell, USCGA US Navy Base Groton.

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: Apr 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

The Cozy Nook

Our Cozy Nook is a comfortable and spacious apartment with an open floor plan. Nestled in a peaceful country neighborhood makes it a relaxing get away. Nearby we have endless hiking trails, beaches, the Connecticut River and cozy villages with delicious dining, two professional theaters, galleries and one of a kind shops. The Nook offers a warm and welcoming place to stay while enjoying the surrounding area.