
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
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Vacation rentals for every style
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Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals

Chic Coastal Retreat: Modern Apt Steps from Beach

Montauk Heaven, Beach & Woods

Beautiful Airy Barn in Springs

House on Little River / Writer Retreat

59 Old Maids Lane pool house

Waterfront carriage house studio

Charming 2BR Cottage, Walk to Town

Amadeus "English Garden Studio"
Guest house rentals with a patio

The Creekside Cottage

Cottage in Quiet Corner. Four miles from town.

Guesthouse at Bantam Woods - 2 bedrooms

Merry Hall Farmhouse

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT

Bayfront 1BR/2BR detached guesthouse with pool

Page Guest House

Cozy remodeled Cottage
Guest house rentals with a washer and dryer

The Blacksmith Cottage

Brand new & close to casinos with HOT TUB

The Barn by the Sound

Ocean Shire Coastal Retreat + Beach Pass

Entire Guest House at Fox Pond Farm.

Tranquil getaway cottage in charming neighborhood

Super Adorable Cottage + Fire pit + King Bed!

Fishing Lodge on Large Country Estate
Destinations to explore
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Six Flags New England
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Woodmont Beach
- Amagansett Beach
- Quotonset Beach
- Ocean Beach Park
- Giants Neck Beach
- Jennings Beach
- Seaside Beach
- Blue Shutters Beach
- Silver Sands Beach
- Bayview Beach
- South Jamesport Beach
- Attawan Beach
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes