Vacation Rentals in Chatham, MA: Compare 10+ Sites & Save

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  5.  Chatham

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914 Best Vacation Rentals in Chatham (Starting from $318)

Walk to Main St and Oyster Pond in Chatham
Walk to Main St and Oyster Pond in Chatham
House
Chatham, MA, USA
0.2k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
7.0

Good

1 reviews

$318
Average price / night
Check Availability
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms12 Guests
10.0

Exceptional

18 reviews

$1709
Average price / night
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Walk to Oyster Pond and Main Street Chatham
Walk to Oyster Pond and Main Street Chatham
House
Chatham, MA, USA
0.2k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
8.0

Good

1 reviews

$1074
Average price / night
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Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Cottage
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$916
Average price / night
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32 Bearses By Way Chatham Cape Cod - - Chatterbox
32 Bearses By Way Chatham Cape Cod - - Chatterbox
House
Chatham, MA, USA
0.2k from Chatham center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom8 Guests
10.0

Exceptional

1 reviews

$1050
Average price / night
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Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$1018
Average price / night
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Centrally Located Home w Patio Fire Pit
Centrally Located Home w Patio Fire Pit
House
Chatham, MA, USA
0.3k from Chatham center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms9 Guests
9.0

Fabulous

2 reviews

$1183
Average price / night
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Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Hot Tub, Internet, Laundry, Microwave, No Smoking, Patio, TV

3 Bedrooms6 Guests
New to Booking
$845
Average price / night
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Oyster Beach Bungalow
Oyster Beach Bungalow
Apartment
Chatham, Massachusetts, USA
0.4k from Chatham center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Bungalows

1 Bedroom2 Guests
8.2

Very Good

14 reviews

$367
Average price / night
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22 Veterans’ Field Rd., Chatham, MA: Home Plate
22 Veterans’ Field Rd., Chatham, MA: Home Plate
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms12 Guests
9.8

Exceptional

14 reviews

$768
Average price / night
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Full Renovation Amazing Spot with Views
Full Renovation Amazing Spot with Views
House
Chatham, MA, USA
0.6k from Chatham center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms4 Guests
9.6

Exceptional

8 reviews

$593
Average price / night
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms9 Guests
10.0

Exceptional

29 reviews

$881
Average price / night
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B By the Sea
B By the Sea
House
Chatham, MA, USA
0.7k from Chatham center

Wheelchair Accessible, Security/Safety, Sports/Activities, Restaurant, Laundry, Barbecue/Outdoor Cooking, Air Conditioner

2 Bedrooms4 Guests
8.7

Fabulous

3 reviews

$456
Average price / night
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Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
10.0

Exceptional

15 reviews

$343
Average price / night
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40 Tip Cart Drive Chatham Cape Cod - The Hideaway
40 Tip Cart Drive Chatham Cape Cod - The Hideaway
House
Chatham, MA, USA
0.7k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom7 Guests
New to Booking
$894
Average price / night
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Carriage House with Beautiful Water View, Steps to Beach & Main Street
Carriage House with Beautiful Water View, Steps to Beach & Main Street
Cottage
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

26 reviews

$410
Average price / night
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Walk to Downtown Chatham Steps to Beach
Walk to Downtown Chatham Steps to Beach
House
Chatham, MA, USA
0.8k from Chatham center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$999
Average price / night
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Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
House
Chatham, MA, 02633, United States
0.2k from Chatham center

AC, Barbecue, Kitchen, Laundry, Microwave, No Smoking, Patio, TV, Washer

2 Bedrooms5 Guests
New to Booking
$1071
Average price / night
Check Availability
388 Main Street Chatham Cape Cod - - The Priscilla House
388 Main Street Chatham Cape Cod - - The Priscilla House
House
Chatham, MA, USA
0.8k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom18 Guests
New to Booking
$1711
Average price / night
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Walk to town and beach from this updated 3BR house in historic Chatham
Walk to town and beach from this updated 3BR house in historic Chatham
House
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$906
Average price / night
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Steps to Oyster Pond Private Dock!
Steps to Oyster Pond Private Dock!
House
Chatham, MA, USA
0.9k from Chatham center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1961
Average price / night
Check Availability
Charming house located in the heart of downtown Chatham!
Charming house located in the heart of downtown Chatham!
House
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Barbecue, Laundry, Microwave, No Smoking, Patio, TV, Washer

3 Bedrooms8 Guests
8.0

Good

2 reviews

$762
Average price / night
Check Availability
Blue water views and coral sunsets from every room in this beautifully appointed home.
Blue water views and coral sunsets from every room in this beautifully appointed home.
House
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Barbecue, Laundry, Microwave, No Smoking, Patio, Toys, TV, Washer

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1184
Average price / night
Check Availability
Wonderful cottage located in the heart of downtown Chatham......steps to everything.
Wonderful cottage located in the heart of downtown Chatham......steps to everything.
Cottage
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Barbecue, Laundry, Microwave, No Smoking, Patio, TV, Washer

2 Bedrooms6 Guests
9.8

Exceptional

11 reviews

$611
Average price / night
Check Availability
Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
House
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$1017
Average price / night
Check Availability
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio
Apartment
Chatham, MA, 02633, United States
0.3k from Chatham center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Toys

1 Bedroom2 Guests
10.0

Exceptional

19 reviews

$398
Average price / night
Check Availability
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
House
Chatham, MA, 02633, United States
0.4k from Chatham center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
9.8

Exceptional

76 reviews

$502
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chatham.

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Frequently Asked Questions

You can explore 914 verified vacation rentals in Chatham. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Chatham vary depending on the season, property size, and location. Rates typically start from around $318 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Chatham include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Chatham welcome pets. Currently, 39 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Chatham often include amenities such as Fireplace/Heating, View, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.