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Results: 135 Rentals

  • Cape Escape - Family-Friendly Chatham Retreat
    From $422 per night (USD)

    VRBO

    Cape Escape - Family-Friendly Chatham Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...

    From $422 per night (USD)

    VRBO

    Details
  • Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach
    From $483 per night (USD)

    Expedia

    Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...

    From $483 per night (USD)

    Expedia

    Details
  • Chatham Cape Cod Near Bike Trail, 1 Mile to Beach!
    From $384 per night (USD)

    VRBO

    Chatham Cape Cod Near Bike Trail, 1 Mile to Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps f ...

    From $384 per night (USD)

    VRBO

    Details
  • Home near beach & tennis/basketball court with firepit, grill, & patio
    From $429 per night (USD)

    Expedia

    Home near beach & tennis/basketball court with firepit, grill, & patio

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Sea Star Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...

    From $429 per night (USD)

    Expedia

    Details
  • Dogs welcome, huge yard right next to Rail Trail!
    From $617 per night (USD)

    VRBO

    Dogs welcome, huge yard right next to Rail Trail!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Summary: 17745 - Happy Tails: Dogs welcome, huge yard right next to Rail Trail! The Space: Discover Coastal Elegance in ...

    From $617 per night (USD)

    VRBO

    Details
  • Roof Deck, Walk to Forest Beach, Fire Pit!
    From $679 per night (USD)

    Expedia

    Roof Deck, Walk to Forest Beach, Fire Pit!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit! The Space: Inn Bloom is perched on a small hills ...

    From $679 per night (USD)

    Expedia

    Details
  • Movie Theater Room, Direct Access to Bike Trail!
    From $475 per night (USD)

    VRBO

    Movie Theater Room, Direct Access to Bike Trail!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Summary: 16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail! The Space: Escape to this charming Chatham ...

    From $475 per night (USD)

    VRBO

    Details
  • Walk to Private Beach on Buck's Pond!
    From $211 per night (USD)

    Expedia

    Walk to Private Beach on Buck's Pond!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Summary: 17721 - Float On: Walk to Private Beach on Buck's Pond! The Space: Welcome to your dream vacation home nestled ...

    From $211 per night (USD)

    Expedia

    Details
  • Waterfront home with lovely lake views, great deck, sun porch & fireplace
    From $786 per night (USD)

    VRBO

    Waterfront home with lovely lake views, great deck, sun porch & fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Mill Pond Vista Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...

    From $786 per night (USD)

    VRBO

    Details
  • Let your Chatham traditions begin here!
    From $356 per night (USD)

    VRBO

    Let your Chatham traditions begin here!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    From the moment you walk into our charming single floor cottage you are invited to relax and unwind. Whether it is coffe ...

    From $356 per night (USD)

    VRBO

    Details
  • Affordable Family Getaway Sleeps 7, Near Bike Path, Beach, Golf, Harwich Center
    From $407 per night (USD)

    VRBO

    Affordable Family Getaway Sleeps 7, Near Bike Path, Beach, Golf, Harwich Center

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Cape-style home in a family-friendly neighborhood. Open floor plan with large living room and dining room (seating for 6 ...

    From $407 per night (USD)

    VRBO

    Details
  • Chatham Home w/ Spacious Deck: 2 Mi to Beaches!
    From $372 per night (USD)

    VRBO

    Chatham Home w/ Spacious Deck: 2 Mi to Beaches!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Experience beachside bliss in Cape Cod when you stay at this 4-bedroom, 3-bath South Chatham vacation rental! This home ...

    From $372 per night (USD)

    VRBO

    Details
  • Walk to Pleasant St Beach!
    From $381 per night (USD)

    VRBO

    Walk to Pleasant St Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable and Charming Cottage, on a beautifully landscaped, private lot and walkable to one of Chatham's beautiful be ...

    From $381 per night (USD)

    VRBO

    Details
  • Chatham Tails & Trails!
    Click For Pricing

    Expedia

    Chatham Tails & Trails!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Charming three-bedroom home in quiet neighborhood! One floor living, this home offers a queen bed in each of the three ...

    Click For Pricing

    Expedia

    Details
  • Chatham EsCAPE: Pet Friendly!
    From $478 per night (USD)

    VRBO

    Chatham EsCAPE: Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This charming 3-bedroom, 2-bathroom home is ideally situated between the tranquil Ridgevale Beach and the vibrant Chatha ...

    From $478 per night (USD)

    VRBO

    Details
  • Two-story dog-friendly retreat with enclosed yard, playset, W/D, & firepit
    From $367 per night (USD)

    Expedia

    Two-story dog-friendly retreat with enclosed yard, playset, W/D, & firepit

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Sand Dollar Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $367 per night (USD)

    Expedia

    Details
  • Waterfront Home With Dock and Two Water Facing Decks! (2372)
    From $529 per night (USD)

    VRBO

    Waterfront Home With Dock and Two Water Facing Decks! (2372)

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of ...

    From $529 per night (USD)

    VRBO

    Details
  • Peaceful Patio near Beach!
    Click For Pricing

    Expedia

    Peaceful Patio near Beach!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Great for two families and near Ridgevale Beach! This house is located in a quiet neighborhood on a cul-du-sac. A perf ...

    Click For Pricing

    Expedia

    Details
  • Renovated Chatham Compound on Bike Path, Less Than a Mile to the Beach
    From $1022 per night (USD)

    VRBO

    Renovated Chatham Compound on Bike Path, Less Than a Mile to the Beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    This newly designed charming Chatham compound can sleep over 10 guests with 2 bedrooms in the main house, 2 bedrooms in ...

    From $1022 per night (USD)

    VRBO

    Details
  • Cozy Chatham Getaway- minutes to all things Cape Cod- New listing!
    From $535 per night (USD)

    VRBO

    Cozy Chatham Getaway- minutes to all things Cape Cod- New listing!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to your perfect beach getaway in beautiful Chatham! This charming four-bedroom, two-bathroom cottage is just 2 m ...

    From $535 per night (USD)

    VRBO

    Details
  • Beautiful Chatham,  Sun Sand & Surf.  8/10 mile to  beaches ,pet friendly home
    From $537 per night (USD)

    VRBO

    Beautiful Chatham, Sun Sand & Surf. 8/10 mile to beaches ,pet friendly home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Island view is a beautiful Chatham beach house Located in a quite cul- de- sac , think about the warm tranquil mornings ...

    From $537 per night (USD)

    VRBO

    Details
  • Rhododendron Cottage – Walk to Cockle Cove
    From $605 per night (USD)

    Expedia

    Rhododendron Cottage – Walk to Cockle Cove

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...

    From $605 per night (USD)

    Expedia

    Details
  • “Mermaid’s Rest” Quiet South Chatham 2-Bedroom House, Close To Beaches
    From $419 per night (USD)

    VRBO

    “Mermaid’s Rest” Quiet South Chatham 2-Bedroom House, Close To Beaches

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    “Mermaid’s Rest” is a well kept 2 bedroom Chatham home just a short drive from popular Rigdevale, Cockle Cove, and Hardi ...

    From $419 per night (USD)

    VRBO

    Details
  • New 2025 Chatham Hideaway - Peaceful Woodland Overlooking Minister's Pond
    From $739 per night (USD)

    VRBO

    New 2025 Chatham Hideaway - Peaceful Woodland Overlooking Minister's Pond

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Welcome to Chatham Hideaway! This sprawling estate, surrounded by woodland and lush gardens, offers a private setting fo ...

    From $739 per night (USD)

    VRBO

    Details
  • Secluded, Walk to Rail Trail, Dog-Friendly Oasis
    From $409 per night (USD)

    VRBO

    Secluded, Walk to Rail Trail, Dog-Friendly Oasis

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to a secluded Cape Cod oasis we call the Hidden Hollow. This beautiful, family-friendly home features a cozy fire ...

    From $409 per night (USD)

    VRBO

    Details
  • Cozy Retreat in South Chatham (2374)
    From $466 per night (USD)

    Expedia

    Cozy Retreat in South Chatham (2374)

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our cozy single-family home located in beautiful South Chatham. This property features 3 comfortable bedrooms ...

    From $466 per night (USD)

    Expedia

    Details
  • Cozy cottage in delightful country side neighborhood!
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    VRBO

    Cozy cottage in delightful country side neighborhood!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to this cozy three-bedroom, two-bath cottage nestled in a peaceful countryside neighborhood. With central air, hi ...

    Click For Pricing

    VRBO

    Details
  • Half Mile Walk to Beach, Dog Friendly!
    From $368 per night (USD)

    Expedia

    Half Mile Walk to Beach, Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: 16691 - Seaside: Half Mile Walk to Beach, Dog Friendly! The Space: Located in the coveted Ridgevale Beach area ...

    From $368 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom house in fabulous Harwich 1 mile from Red River Beach
    From $307 per night (USD)

    VRBO

    Charming 3-bedroom house in fabulous Harwich 1 mile from Red River Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Consider this house your home away from home while you visit Harwich. With 3 bedrooms, 2 bathrooms, and essential amenit ...

    From $307 per night (USD)

    VRBO

    Details
  • NEW LISTING! Northside Dennis 4BD--A/C, Close to Popular Dennis Beaches
    From $595 per night (USD)

    VRBO

    NEW LISTING! Northside Dennis 4BD--A/C, Close to Popular Dennis Beaches

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    NEW LISTING! Large 4 Bedroom, 3 Bath Northside Dennis home. A comfortable Cape escape offering spacious rooms and a conv ...

    From $595 per night (USD)

    VRBO

    Details
  • Family Tides Ridgevale Beach Getaway!
    Click For Pricing

    VRBO

    Family Tides Ridgevale Beach Getaway!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Short walk to Ridgevale Beach! This 3 bedroom house (king, 4 twins) and 2 full baths allows plenty of space for the enti ...

    Click For Pricing

    VRBO

    Details
  • Porch, Paws and Sandy Beaches
    Click For Pricing

    Expedia

    Porch, Paws and Sandy Beaches

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Spacious Farmer's Porch and close to Forest Beach!! Cozy 4BR (Queen, King, 4 Twins) 1.5 Bath in South Chatham! Grab the ...

    Click For Pricing

    Expedia

    Details
  • Waterfront 3-BR House w Hot tub: kayak/canoe up the tidal river to Pleasant Bay!
    From $436 per night (USD)

    VRBO

    Waterfront 3-BR House w Hot tub: kayak/canoe up the tidal river to Pleasant Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Get ready to relax in this 3-bedroom house in Chatham. This wonderful riverfront property features a 7-person hot tub wi ...

    From $436 per night (USD)

    VRBO

    Details
  • Chatham Vineyard View
    From $511 per night (USD)

    Expedia

    Chatham Vineyard View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Escape to this cozy three-bedroom, two-bath cottage nestled on a private cul-de-sac. A bright and sunny sunroom adds ter ...

    From $511 per night (USD)

    Expedia

    Details
  • Mooncusser Cottage on Taylor's Pond!
    From $598 per night (USD)

    VRBO

    Mooncusser Cottage on Taylor's Pond!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Mooncusser! Fabulous two bedroom (1 king, 2 doubles) with a den (sleep sofa) waterfront cottage on saltwater ...

    From $598 per night (USD)

    VRBO

    Details