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Chatham Family Retreat w/ Heated Pool

Outdoor swimming pool and paved patio adjacent to a shingle-style house with an elevated deck and barbecue grill.Kitchen with white cabinetry, light countertops, wood flooring, a central island with sink, and a skylight overhead.Exterior view of a multi-section shingle and siding home with a paved driveway in the foreground.Dining room with a long wooden table, white chairs, light blue walls with white wainscoting, and wood flooring.Living room with a large gray sectional sofa, a coffee table, a mounted flat-screen TV over a white media console, and wood flooring.Sunlit outdoor deck with outdoor dining table, chairs, and wicker seating against a shingled house.Outdoor swimming pool bordered by blooming pink and purple hydrangeas and lounge chairs on the patio.Bright kitchen featuring white cabinetry, light countertops, an island with an integrated sink, vaulted ceilings, and a skylight.Outdoor swimming pool illuminated with blue and purple lighting at night, flanked by lounge chairs and pool floats.An outdoor swimming pool bordered by stone pavers and blooming hydrangea bushes.Nighttime view of an outdoor swimming pool illuminated with blue and green underwater lights, surrounded by blooming hydrangea bushes and string lights.Outdoor swimming pool bordered by blooming pink and purple hydrangeas with lounge chairs on the patio.Exterior rear view of a multi-story shingled home with a fenced yard and grassy lawn under a blue sky.Outdoor wood dining table and chairs set on a grey deck beside a shingled house.Bright kitchen featuring a granite-topped island with wooden barstools, white cabinetry, stainless steel appliances, and a skylight.A kitchen with white cabinets, stainless steel appliances, a center island with a stool, and a vaulted ceiling with a skylight.Dining room with light blue walls, white wainscoting, wood flooring, a central dining table with white chairs, and a corner built-in cabinet.Living room with yellow walls, wood flooring, a brick fireplace, a dark leather sofa, and two armchairs.Exposed red brick fireplace with a thick wooden mantel, mesh screen, and nautical decor in a room with yellow walls.Sunlit sitting room with a brown sofa, a wooden rocking chair, built-in bookshelves, and a telescope facing the windows.Bedroom with sloped ceiling, wood flooring, a made bed, white dressers, a rocking chair, and two windows.Bedroom with a bed made with a blue comforter and stacked towels, flanked by white nightstands and bedside lamps under a sloped ceiling.Nautical anchor lamp glowing on a white dresser in an indoor room with a window and round mirror.A white wicker armchair with a patterned cushion sits on carpet next to low shelving under a sloped ceiling.Bedroom featuring a daybed with seashell bedding, hardwood floors, a coastal-patterned area rug, and a white dresser set between two windows.Bedroom featuring wood flooring, a patterned coastal area rug, a white dresser, and a bed under a sloped ceiling.Bathroom with dark blue square floor tiles, a toilet, a vanity counter with a large mirror, and an overhead skylight.Bathroom with light blue walls, white wainscoting, a vanity with large mirror, and a toilet next to a window.Bathroom featuring a bathtub and shower combination enclosed by sliding glass doors with white subway tile surround.Bedroom with wood-paneled walls, hardwood floors, a skylight, a bed with a white headboard, and track lighting.Bedroom with vaulted ceiling, skylights, wood-paneled walls, hardwood floors, a main bed with blue-and-white striped bedding, and an additional daybed.Bedroom with vertical wood paneling, a bed beneath a skylight, a bedside table with lamp, and track lighting.Bedroom with wooden paneled walls, wood flooring, a bed positioned under a skylight, and an adjacent open doorway.Bedroom with blue striped bedding, a rocking chair, hard-surface floors, and a blue area rug.Bedroom with a striped bedspread, white nightstands, and a wooden rocking chair set beside bay windows.Bathroom with white vanity, light countertop, large mirror, and toilet beside beige walls and tiled floor.Bathroom showing a white toilet, tiled flooring, vanity counter edge, towel ring, and a walk-in shower with a coastal-themed curtain.Close-up of a hanging pendant light with an illuminated vintage-style bulb, with an out-of-focus dining room and rocking chair in the background.A brightly lit entryway hallway with light wood floors, a runner rug, closet doors, and wall decorations leading to an open living area.Entryway with light hardwood floors looking past a small counter peninsula into a bright kitchen with white cabinetry.Sunlit open living and dining area featuring hardwood floors, a wooden rocking chair, a dining table with chairs, and a wall-mounted TV.Dining area with light wood floors, a wooden dining table and chairs, a three-light chandelier, and windows looking out to the yard.Close-up of a green metal compass rose wall decoration, with a dining table and chairs visible in the blurred background.Bathroom with white vanity, toilet, seashell mirror, and a window.A small dormer alcove featuring a turquoise desk, a white wooden chair, carpeted flooring, and a window overlooking outdoor greenery.Bedroom with a blue upholstered bed, sloped ceiling, windows with curtains, and a side chair.Spacious bedroom with carpet flooring, a large blue upholstered bed, white dresser with mirror, and multiple windows.Bathroom with white tiled floor, long blue double vanity, and a separate doorway leading to a toilet area.Bathroom with white tiled flooring, a long double vanity with teal-blue cabinetry, large mirrors, and an open doorway leading to a carpeted room.Bathroom with white subway tile floor, a toilet beside a window, and a glass-enclosed shower beneath a skylight.A wooden platform tree fort built between trees in a wooded area with fallen autumn leaves.Outdoor yard play area with a boat-shaped sandbox, a mesh hammock, and a tree swing.Nighttime outdoor view of a covered swimming pool illuminated by string lights along a garden bed with blooming hydrangea bushes under a dark sky.Exterior front view of a two-story white house with green shutters, a porch, a lawn, and an asphalt driveway under a twilight sky.Exterior of a multi-story home with wood shingle and white siding, green shutters, front porch, and paved driveway.Front exterior of a two-story white house with green shutters, a bay window, and a covered porch.Front porch of a house with decorative posts, green shutters, white rocking chairs, and dried hydrangea bushes alongside the mulched garden bed.Exterior view of a multi-story home with shingle siding, a front porch, and a large deciduous tree in the yard.An outdoor swimming pool bordered by blooming purple, pink, and white hydrangeas, with lounge chairs in the background.Exterior covered porch with decorative white columns, green shutters, and outdoor chairs.Exterior of a white two-story house with green shutters, a covered porch, and cornhole boards set up on the front lawn.Front-loading metallic washer and dryer set placed side by side beneath built-in shelving holding laundry baskets.
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House in Chatham, Massachusetts

12 guests • 5 bedrooms • 9 beds • 3 full baths • 2 half baths
Chatham Retreat with Heated Pool, Spacious Deck & Direct Rail Trail Access Welcome to your Chatham getaway—an updated, two-story 5BR/3.5BA home designed for effortless Cape Cod living. Set on a generous lot with a private heated pool and direct access to the Old Colony Rail Trail, this inviting retreat puts you minutes from Chatham’s beaches, charming Main Street, and favorite local eateries. Bike downtown for seafood at the iconic Chatham Squire, then grab ice cream on your way back. Relax outdoors on the expansive deck overlooking the pool, gather for alfresco meals, or enjoy a friendly game of bocce in the backyard. With the bike path right at your doorstep, adventure begins the moment you head outside. Perfect for families and groups, this home features three comfortable living areas: Main living room: Spacious sectional with seating for 10 and a flat-screen TV. Cozy lounge: Seating for four—ideal for quiet mornings or evening wind-downs. Sunlit sitting room: Comfy sofa with peaceful views of the pool and backyard. The fully equipped kitchen features warm wood cabinetry, granite countertops, skylights, and a full suite of stainless steel appliances—including a double-door fridge with ice and water dispenser. Formal dining room with seating for 8, plus a kid's table for 4. Additional Casual dining area for 6 and Kitchen island seating for 3. This spacious home sleeps up to 12 guests across five bedrooms: Primary Suite: King bed, large walk-in closet, and en-suite bath with double vanity and walk-in shower. Bedroom 2: Queen bed and private en-suite bath with walk-in shower. 1st floor in separate wing of the house. Bedroom 3: Queen bed with sliding-door access to Bedroom 4 (connected): Twin bed with pull-out trundle and a private half bath—great for kids. (Upstairs.) Bedroom 5: Queen bed plus two twin beds (convertible into a full). (Upstairs) A guest bathroom with a tub/shower combination serves the upper level, and an additional half bath adds convenience. Outdoors The property’s outdoor amenities are ideal for summer fun: Private heated salt-water pool (open Memorial Day–Labor Day) Large deck with dining and lounging space Refreshing outdoor shower Spacious yard with room to play - fort, sandbox, playhouse, swing Extras Complimentary Wi-Fi, cable TV & Netflix Washer/dryer Driveway parking for 4 cars Heat pump Air throughout home with separate Air conditioners in two bedrooms + multiple fans Chatham’s best attractions are right at your fingertips. Direct access to Old Colony Rail Trail—bike or walk to town 1.5 miles to Chatham’s Main Street shops, galleries & restaurants 1.2 miles to Oyster Pond 2.2 miles to Lighthouse Beach 1 mile to Veteran's Field for Chatham A's games, part of the famed Cape Cod Baseball League Close to Hangar B Eatery, freshwater ponds, and the Monomoy National Wildlife Refuge (3.5 miles) Easy walking distance to two coffee shops and four restaurants Whether you're gathering for a family vacation or a coastal getaway with friends, this sunlit, activity-filled home offers the perfect backdrop for your Chatham escape.
What this place offers
  • Kid-friendly dishes
  • Bathtub
  • Shower
  • Hair dryer
  • Outdoor shower
  • Board games
  • Books
  • TV
  • Air conditioning
  • Baking sheet
Where you'll sleep
Bedroom 1
1 queen
Bedroom 2
1 queen
Bedroom 3
1 trundle bed (2 twins)
Bedroom 4
1 queen, 2 twins
Bedroom 5
1 king
Library
1 full
Chatham, MA, USA
House rules
  • Check-in after 4:00 PM
  • Check-out before 10:00 AM
  • 12 guests maximum
Safety & property
  • Exterior security cameras on property
  • Carbon monoxide alarm installed
  • Fire extinguisher
Cancellation policy
Add your trip dates to get the cancellation details for your stay.

This property is managed through Fairly. It is also available on sites like Airbnb and Vrbo, but the lowest price is always at Fairly.com. Avoid service fees by booking direct.

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