Pet-friendly vacation rentals in Middlesex County

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

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.

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Seagrass Bungalow

🌾Seagrass Bungalow is a sun filled, romantic, peaceful, back to nature, mini-home, that is exactly where you are meant to be! Private & surrounded by seagrass blowing in the breeze & cheerful birds waking you with the sunrise. Seagrass Bungalow is the perfect getaway for two & their small pup. Do yoga on the private deck, shower outdoors in the sunlight, grill local corn, have a cocktail by the firepit, or get out & walk to the cutest town green, shops, restaurants, & beach! ☀️

Hot Tub & Cloud Ceiling House 5 min to Mohegan Sun

Stay at a one-of-a-kind house located 5 minutes from Mohegan Sun and several other attractions close by. Our house is conveniently located close to Foxwoods, Mystic, vineyards, Navel Submarine Base, Ct College, USCG Academy and several beaches. Enjoy our game room where you can play arcade games, pool, foosball, giant connect 4, hooky, board games and sing karaoke all under a light up cloud ceiling. Relax in the hot tub or by the gas fire pit in our private backyard.

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Lakeside Getaway Tiny House

Welcome to the Lakeside Getaway! This cozy tiny home offers the perfect mix of relaxation and convenience. Enjoy all the comforts of home in a small, well though out space set in nature with a huge picture window showcasing stunning views of Pattagansett. This tiny house features a full-size shower, heat, hot water, flush toilet, full-size fridge, and a 2-burner cooktop. Your serene escape awaits!

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

1 Bed Cabin - Postcard Cabins Machimoodus

Welcome to Postcard Cabins, your picture-perfect nature destination. A scenic two-hour drive from the city, our collection of design-forward tiny cabins is set across acres of private woodlands, offering space to slow down and immerse yourself in nature—while still enjoying the comforts of a boutique stay.