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Family-friendly vacation rentals in Madison

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Top-rated family-friendly rentals in Madison

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Rental unit in East Haddam

4.78 out of 5 average rating, 274 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

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”.

Rental unit in Middletown

4.94 out of 5 average rating, 756 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Home in East Haven

4.88 out of 5 average rating, 216 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Home in North Fork

4.95 out of 5 average rating, 334 reviews

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Cottage in Middlefield

4.92 out of 5 average rating, 244 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Loft in Essex

4.94 out of 5 average rating, 429 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Guest suite in North Fork

4.88 out of 5 average rating, 638 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Home in Cheshire

5 out of 5 average rating, 128 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

Guest suite in New Haven

4.99 out of 5 average rating, 176 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Vacation rentals for every style

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Stylish accommodations and amenities

Popular amenities for Madison family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in North Fork

4.97 out of 5 average rating, 201 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Home in Sag Harbor

4.96 out of 5 average rating, 91 reviews

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

Home in East Hampton

4.94 out of 5 average rating, 72 reviews

Family Friendly Springs Beach House

Home in Shippan Point

4.94 out of 5 average rating, 113 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

Farm stay in Kent

4.88 out of 5 average rating, 293 reviews

(°) The Wandering Peacock (°)

Home in North Fork

4.96 out of 5 average rating, 52 reviews

Mattituck Dream House - Summer Rental Opportunity

Villa in Norwich

4.89 out of 5 average rating, 383 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

Home in Shelter Island

4.9 out of 5 average rating, 79 reviews

Shangri-la Cedar Cottage on Shelter Island

Family- and pet-friendly home rentals

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Cabin in New Milford

4.84 out of 5 average rating, 128 reviews

A-Frame Cottage off Candlewood Lake

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Cottage By The Sea

Guest suite in Waterbury

4.94 out of 5 average rating, 263 reviews

Private 1 bedroom apartment in central Connecticut

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 reviews

Quiet 2 bed room apt w/ private entrance.

Home in Litchfield

4.93 out of 5 average rating, 177 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Home in Montauk

4.88 out of 5 average rating, 198 reviews

Studio MTK Bungalow. Short Walk to Beach & Town!

Family-friendly home rentals with a pool

Home in Montville

4.91 out of 5 average rating, 254 reviews

Casino Wine Down House***

Home in New London

4.91 out of 5 average rating, 175 reviews

Sunset Oasis @ Ocean Beach: $1Mil View w/ 6 Queen

Barn in Bethel

4.98 out of 5 average rating, 222 reviews

Escape to a Restored New England Antique Milk Barn

Home in East Hampton

4.93 out of 5 average rating, 107 reviews

Private & Pristine with Pool and Kid’s Playard

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Home in East Hampton

4.89 out of 5 average rating, 109 reviews

Gorgeous East Hampton Getaway

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Cottage in Montauk

4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

Quick stats about vacation rentals that are family-friendly in Madison

Total rentals
80 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.6K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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