
Guesthouse holiday rentals in Middlesex County
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Top-rated Guesthouses in Middlesex County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County guesthouses
Family-Friendly guesthouses

Quiet setting for this guesthouse with pool.

Charming Post and Beam cottage (near Foxwoods)

Cozy Guest House on 15 Acres

Cozy private one bedroom guest apt suite

Sleek and Chic cottage/Pool House

Chez Nanou- Above the Barn Charm

Flip-flop

True Artist Loft, 5 minutes to downtown Mystic
Guesthouses with a patio

A Little House by the sea

Brand new & close to casinos with HOT TUB

Cozy Private Guest Suite

The Rising Tide Cottage

The Nest. Large studio in the Woods.

Cottage in Quiet Corner. Four miles from town.

Guesthouse at Bantam Woods - 2 bedrooms

Clinton's hidden secret, a Distillerie until 1926
Guest house rentals with a washing machine and dryer

Chic Coastal Retreat: Modern Apt Steps from Beach

Camellia Springs - Solace & Rest

The Creekside Cottage

Mystic Cottage - walk to downtown

59 Old Maids Lane pool house

Private studio guesthouse

The Hospitable Homestead-Kid Friendly & Pets too!

The Gardener's Cottage Dog friendly/weekly/monthly
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Family-friendly rentals Middlesex County
- Rentals with pools Middlesex County
- House rentals Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with a hot tub Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with a fire pit Middlesex County
- Beachfront rentals Middlesex County
- Rentals with lake access Middlesex County
- Fitness-friendly rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with an EV charger Middlesex County
- Private suite rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a patio Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Rentals with a fireplace Middlesex County
- Bed and breakfasts Middlesex County
- Apartment rentals Middlesex County
- Rentals with beach access Middlesex County
- Guesthouse rentals Connecticut
- Guesthouse rentals United States
- Yale University
- Charlestown Beach
- Fairfield Beach
- Foxwoods Resort Casino
- Southampton Beach
- Cooper's Beach, Southampton
- Six Flags New England
- Ocean Beach Park
- Mystic Seaport Museum
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- TPC River Highlands
- Groton Long Point Main Beach
- Brownstone Adventure Sports Park
- Cedar Beach
- Woodmont Beach
- Silver Sands Beach
- Jennings Beach
- Sandy Beach
- Ninigret Beach
- Wildemere Beach
- Seaside Beach