Waterfront vacation rentals in Middlesex County

Cottage in Deep River

Serene Waterfront Cottage

Welcome to Smuggler’s Cove Cottage. Rumor has it that this quaint cottage was once the scene of infamous rum running. Today, it’s our little slice of heaven away from the chaotic city life. It’s the perfect place to curl up and read a book by the fire when it’s chilly out. During the warmer months, take full advantage of the spacious waterfront patio & docks. Whether you’re sunbathing or having a drink watching the local geese and ducks float by, this tranquil cottage has everything you need.

Nov 2 – 9

Home in East Hampton

Lake Fun: PingPong, Pool Table, Slide, EV Charger

Fun on Lake Pocotopaug - Fun on the water with swimming, kayaks, rowboat, and paddle boards; fun on land with ping pong, pool table, puzzles, and many games. Gather around the fire pit at night & roast marshmallows. In central CT with easy day trips to Mystic Seaport & Aquarium, Gillette Castle, Mark Twain House and so much more. Close to renowned musical theater at Goodspeed Opera House. Hiking and mountain biking possibilities galore at close by state parks. EV CHARGER FOR YOUR USE IN GARAGE

Jan 5 – 12

Apartment in Branford

Stony Crk Studio ideal for trvl nurses…

Peaceful shoreline studio/retreat for trvl nurses, grad students etc near New Haven. Single occupancy studio comprises upper east-wing of our home—has its own entrance up the exterior stairway with a dbbl-locked interior door and soundproofing for your privacy. Enjoy the balcony views and sunny chaise lounge chairs in rear-garden. Kick off your shoes and totally RELAX in our sleepy niche called Stony Creek, where the beach and harbor, food and shops & historic Thimble Islands are steps away.

Oct 20 – 27

Apartment in Chester

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

Dec 17 – 24

Vacation home in Guilford

Spacious Oceanfront Getaway with Spectacular Views

Perfect summer getaway! Awaken to the sun rising over Long Island Sound! Panoramic views from 70 ft of waterfront windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, hike, fish, read a book, or watch sailboats go by! (Not suitable for children/pets.)

Jan 25 – Feb 1

Home in Old Lyme

Relax & Rejuvenate in this 1920s Riverfront Estate

Enjoy your time away by the river in this Old Lyme Estate; where artists lived and loved on the CT Shoreline a century ago. 7 acres of riverside land and privacy, unparalleled bird watching, and a home that is completely set up for your Vacation. Situated on the Lieutenant River with access to LI Sound; fish off the dock, explore in canoes, play piano, workout in the home gym; beaches, tennis, golf. Central A/C, hi-speed WIFI. Nespresso pods included! Come enjoy the peace and tranquility!

Oct 23 – 30

Cottage in Chester

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Feb 6 – 13

Home in Lyme

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature

Guest suite in Portland

Cozy waterview in-law apartment

Take it easy at this tranquil getaway. This inlaw apartment offers beautiful views overlooking the CT river. Featuring its own separate entrance the house has a two story patio, outdoor seating, and fire pit. Next to a marina for easy access to water sports. Location is conveniently between both downtown Middletown and south Glastonbury (about a five min drive either way) and offers a wide variety of restaurants and entertainment. 25 yo age minimum.

Oct 14 – 21