Goose Pond Rentals
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
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
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
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
From $514 per night (USD)VRBO
Poppy's Place: Cape Escape for Family & Friends
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $514 per night (USD)VRBO
Click For PricingExpedia
3-bedroom house in charming Chatham with WiFi, fitness room, AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
Click For PricingExpedia
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
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
Click For PricingVRBO
Chatham Gem with Pool & High-End Style RPAM104
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NEW FOR THE 2025 SEASON! Welcome to your perfect Cape Cod getaway in the heart of Chatham! This stunning 4-bedroom, 3.5- ...
Click For PricingVRBO
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
From $595 per night (USD)VRBO
Nautical Comfort near Rail Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Modern nautical-themed decor abounds in this newly renovated, freshly painted Cape located in West Chatham. On a quiet ...
From $595 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $687 per night (USD)VRBO
Elbow Inn: Private Retreat with Two Master Suites
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This spacious Chatham beach house comfortably sleeps 8, making it the perfect retreat for families or friends. With 4 be ...
From $687 per night (USD)VRBO
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
Click For PricingVRBO
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 PricingVRBO
From $369 per night (USD)VRBO
THREE BEDROOM--MINUTES TO GOOSE POND, PLEASANT BAY AND TOWN.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable home with quiet setting, just short drive to Downtown Chatham, Two Ponds and Beaches. * * * * See e ...
From $369 per night (USD)VRBO
From $480 per night (USD)VRBO
Coastal Comforts Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Create unforgettable memories with your loved ones at this peaceful and private retreat in West Chatham. This spacious t ...
From $480 per night (USD)VRBO
From $527 per night (USD)Expedia
41 Poolside: 041-CS Coastal Retreat in Chatham – Modern Comfort & New Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This property is professionally managed by Pretty Picky Properties. Sleeps 6 Linens included beds made Rents ...
From $527 per night (USD)Expedia
From $336 per night (USD)VRBO
Quintessential Cape Cod Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
My cottage is close to Harding's & Ridgevale beach, Chatham farmer market, convenience stores, restaurants and sandwich ...
From $336 per night (USD)VRBO
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
From $1023 per night (USD)VRBO
Unique Private Chatham Getaway with Lap Pool & Deck Lounge (2403)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your perfect Chatham retreat—new to the rental market and truly one-of-a-kind. Built right into a hillside, t ...
From $1023 per night (USD)VRBO
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
From $820 per night (USD)VRBO
Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to this delightful cottage nestled in picturesque Chatham—your perfect home base for Cape adventures! With 3 comf ...
From $820 per night (USD)VRBO
Click For PricingExpedia
Bright, dog-friendly property located close to Jackknife Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This bright, dog-friendly rental features a fenced yard and is conveniently located near Jacknife Beach. The property in ...
Click For PricingExpedia
Click For PricingVRBO
Charming 4-bedroom house with fresh water dock & shark-free swimming!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this enchanting house in Chatham. This phenomenal home has been completely renovated over the past few years ...
Click For PricingVRBO
From $524 per night (USD)Expedia
North Chatham Retreat – Renovated 3BR, 3.5BA + Bonus, 2900 Sq Ft
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Your North Chatham Retreat – A Perfect Cape Cod Getaway Located in scenic North Chatham and just minutes fro ...
From $524 per night (USD)Expedia