Top Winter Vacations - Vacation Rentals in North Madison Shopping Center

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From US $504

         

10.0 (53 Reviews)

Cabin

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Killingworth

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From US $331

         

|

9.8 (99 Reviews)

Bed & Breakfast

The Homestead

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Madison Center

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From US $368

         

|

10.0 (89 Reviews)

Bed & Breakfast

The Homestead

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Madison Center

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From US $305

         

10.0 (14 Reviews)

House

Enjoy a taste of New England in Historic Guilford Ct

• Air Conditioner
• Parking
• Pet Friendly

• New Haven
• Guilford

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From US $258

         

|

9.5 (43 Reviews)

Bed & Breakfast

Scranton Seahorse Inn

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Madison Center

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From US $108

         

8.8 (61 Reviews)

Hotel

Spark by Hilton Guilford

• Air Conditioner
• Parking
• Pool

• New Haven
• Guilford

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From US $238

         

10.0 (14 Reviews)

House

Cozy Coastal Getaway

• Air Conditioner
• Parking
• TV

• New Haven
• Guilford

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From US $681

         

|

New

House

Cozy Woodland Home! Ski and Hike Coastal Connecticut

• Parking
• Pet Friendly
• Pool

• Old Saybrook
• Killingworth

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From US $103

         

7.4 (233 Reviews)

Hotel

Tower Inn And Suites Of Guilford - Madison

• Air Conditioner
• Parking
• TV

• New Haven
• Guilford

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From US $201

         

10.0 (13 Reviews)

Apartment

Quiet Killingworth Rental w/Deck & Grill!

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Killingworth

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From US $1,267

         

10.0 (7 Reviews)

House

Luxury One-of-a-kind Waterfront Estate w/Pool, Spa, Tennis & Pond Access

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Killingworth

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From US $758

         

10.0 (3 Reviews)

House

Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

• Air Conditioner
• Parking
• TV

• New Haven
• Guilford

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From US $191

         

10.0 (2 Reviews)

House

Charming In-Law Apt with independant entrance in Guilford

• Air Conditioner
• Parking
• TV

• New Haven
• Guilford

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From US $233

         

10.0 (1 Review)

Cottage

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Killingworth

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New

From US $177

         

10.0 (1 Review)

Apartment

Fully equipped studio in the center of town near train, beach and town green

• Air Conditioner
• Security/Safety
• Bedding/Linens

• New Haven
• Guilford

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From US $357

         

9.6 (9 Reviews)

House

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Killingworth

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From US $576

         

9.2 (5 Reviews)

House

Cozy Woodland Home! Ski & Hike Coastal Connecticut

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Killingworth

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From US $1,033

         

New

Cabin

Spectacular Lake Front Cabin close to CT shoreline

• Air Conditioner
• Parking
• Security/Safety

• New Haven
• Guilford

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From US $390

         

New

Cottage

Available July 1, 2025 2 week or monthly.

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Madison

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From US $293

         

New

Apartment

Beautiful Beachy Guesthouse, Antiques & Charm, 5 Min to Beach & Town

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Madison Center

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From US $242

         

New

Cottage

WITH INN —Charming 2-bedroom cottage in Guilford with WiFi and AC

• Air Conditioner
• Security/Safety
• Bedding/Linens

• New Haven
• Guilford

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From US $191

         

10.0 (86 Reviews)

Apartment

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Madison

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From US $504

         

10.0 (41 Reviews)

House

Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Madison

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From US $350

         

10.0 (26 Reviews)

House

Quiet 2 bedroom summer haven overlooking beautiful West River

• Air Conditioner
• Parking
• Pet Friendly

• New Haven
• Guilford

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