
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

Beautiful Airy Barn in Springs

Farmington River Carriage House Pleasant Valley CT

Hidden Haven

Entire Guest House at Fox Pond Farm.

Historic Railroad Caboose - Unique CT Farm Escape

The Pool Cottage at Narrow Valley Estate

Charming Post and Beam cottage (near Foxwoods)

Waterfront Guesthouse
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

Cottage in Quiet Corner. Four miles from town.

Guesthouse at Bantam Woods - 2 bedrooms

Clinton's hidden secret, a Distillerie until 1926

Studio Cottage
Guest house rentals with a washing machine and dryer

Chic Coastal Retreat: Modern Apt Steps from Beach

Camellia Springs - Solace & Rest

The Creekside Cottage

The Nest. Large studio in the Woods.

Super Adorable Cottage + Fire pit + King Bed!

Southold- Adorable 1 Bedroom Cottage

59 Old Maids Lane pool house

Private studio guesthouse
Destinations to explore
- Plainview Holiday rentals
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- Cottage rentals Middlesex County
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- Guesthouse rentals Connecticut
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- 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
- Napeague Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Cedar Beach
- Brownstone Adventure Sports Park
- Groton Long Point Main Beach
- Silver Sands Beach
- Woodmont Beach
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Seaside Beach