Best Chatham Vacation Rentals
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Top location
Oyster Beach Bungalow
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
Oyster Beach Bungalow Chatham offers proximity to nearby tourist spots, such as the Atwood House & Museum, situated merely 13 minutes' walk away.
Oyster Beach Bungalow
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
Oyster Beach Bungalow
Oyster Beach Bungalow Chatham offers proximity to nearby tourist spots, such as the Atwood House & Museum, situated merely 13 minutes' walk away.
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Beach access
Updated Beach House Deck Outdoor Shower!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Updated Beach House Deck Outdoor Shower! Chatham villa is located a 9-minute walk from the Forest Beach and offers guests to enjoy fishing. Located 4.6 km from the Cape Cod Lavender Farm, this holiday home provides high-speed Internet access and private car parking.
Updated Beach House Deck Outdoor Shower!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Updated Beach House Deck Outdoor Shower!
Updated Beach House Deck Outdoor Shower! Chatham villa is located a 9-minute walk from the Forest Beach and offers guests to enjoy fishing. Located 4.6 km from the Cape Cod Lavender Farm, this holiday home provides high-speed Internet access and private car parking.
Sea House
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
Sea House Villa Chatham entices guests to enjoy fishing and offers proximity to the Atwood House & Museum, located just an 8-minute stroll away. Offering high-speed Internet access, the Chatham holiday home is located within a 3-km distance of the Ridgevale Beach.
Sea House
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
Sea House
Sea House Villa Chatham entices guests to enjoy fishing and offers proximity to the Atwood House & Museum, located just an 8-minute stroll away. Offering high-speed Internet access, the Chatham holiday home is located within a 3-km distance of the Ridgevale Beach.
Cheap Chatham Vacation Rentals
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Guest favorite
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Beach access
Full Renovation Amazing Spot With Views
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
The 2-bedroom Full Renovation Amazing Spot With Views Villa Chatham, located merely a 6-minute walk from the Eldredge Public Library, can host up to 4 guests. This 1-bathroom villa features opportunities for fishing in the area, within easy reach of the Kate Gould Park.
Full Renovation Amazing Spot With Views
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Full Renovation Amazing Spot With Views
The 2-bedroom Full Renovation Amazing Spot With Views Villa Chatham, located merely a 6-minute walk from the Eldredge Public Library, can host up to 4 guests. This 1-bathroom villa features opportunities for fishing in the area, within easy reach of the Kate Gould Park.
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Beach access
Pond Front Home W Game Room Dog Friendly
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
The 4-bedroom Pond Front Home W Game Room Dog Friendly Chatham entices guests to enjoy fishing and is located 3.1 km from such natural sites as the Cockle Cove Beach. Providing guests with high-speed Internet access and private parking, this holiday home is around 15 minutes' drive from the Chatham Shark Center.
Pond Front Home W Game Room Dog Friendly
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Pond Front Home W Game Room Dog Friendly
The 4-bedroom Pond Front Home W Game Room Dog Friendly Chatham entices guests to enjoy fishing and is located 3.1 km from such natural sites as the Cockle Cove Beach. Providing guests with high-speed Internet access and private parking, this holiday home is around 15 minutes' drive from the Chatham Shark Center.
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Beach access
Walk To Beach: Chatham Gem W/ Ocean-View Sunroom!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
With the capacity to host 6 guests, the 3-bedroom Walk To Beach: Chatham Gem W/ Ocean-View Sunroom! villa is located around a 10-minute drive from such significant cultural landmarks as the Chatham Railroad Museum.
Walk To Beach: Chatham Gem W/ Ocean-View Sunroom!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
Walk To Beach: Chatham Gem W/ Ocean-View Sunroom!
With the capacity to host 6 guests, the 3-bedroom Walk To Beach: Chatham Gem W/ Ocean-View Sunroom! villa is located around a 10-minute drive from such significant cultural landmarks as the Chatham Railroad Museum.
Pet Friendly Vacation Rentals Chatham Massachusetts
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Beach access
Large Home W Fire Pit And Dogs Welcome
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
The 4-bedroom Large Home W Fire Pit And Dogs Welcome Chatham is located around 6 km from the Chatham Lighthouse and provides fishing for active guests. Providing guests with high-speed Internet access and private car parking, this holiday home is about 10 minutes by car from the family-friendly Oyster Pond Beach.
Large Home W Fire Pit And Dogs Welcome
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Large Home W Fire Pit And Dogs Welcome
The 4-bedroom Large Home W Fire Pit And Dogs Welcome Chatham is located around 6 km from the Chatham Lighthouse and provides fishing for active guests. Providing guests with high-speed Internet access and private car parking, this holiday home is about 10 minutes by car from the family-friendly Oyster Pond Beach.
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Beach access
Beautiful Home W Artistic Flair
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Accommodating up to 7 guests, the 3-bedroom Beautiful Home W Artistic Flair Chatham is situated within a 6-km distance of renowned cultural sites such as the Chatham Railroad Museum. This Chatham holiday home features opportunities for fishing in the area, around a 10-minute drive from the Cockle Cove Beach.
Beautiful Home W Artistic Flair
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Beautiful Home W Artistic Flair
Accommodating up to 7 guests, the 3-bedroom Beautiful Home W Artistic Flair Chatham is situated within a 6-km distance of renowned cultural sites such as the Chatham Railroad Museum. This Chatham holiday home features opportunities for fishing in the area, around a 10-minute drive from the Cockle Cove Beach.
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Great deal
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Beach access
1 Mile From Downtown Chatham Walk To Pier
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
The 4-bedroom 1 Mile From Downtown Chatham Walk To Pier villa is located 19 minutes' walk from the Eldredge Public Library and invites guests to join fishing. The holiday home hosts up to 10 guests and provides them with private car parking.
1 Mile From Downtown Chatham Walk To Pier
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
1 Mile From Downtown Chatham Walk To Pier
The 4-bedroom 1 Mile From Downtown Chatham Walk To Pier villa is located 19 minutes' walk from the Eldredge Public Library and invites guests to join fishing. The holiday home hosts up to 10 guests and provides them with private car parking.
Chatham Vacation Rentals Oceanfront
Ping-Pong & Backyard: Spacious Chatham Retreat
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Sun loungers
The 3-bedroom Ping-Pong & Backyard: Spacious Chatham Retreat villa hosts up to 8 guests and is nestled 2.6 km from natural sites such as the Ridgevale Beach. Located around 10 minutes' drive from the Chatham Shark Center, this property provides Wi-Fi and private parking.
Ping-Pong & Backyard: Spacious Chatham Retreat
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Sun loungers
Ping-Pong & Backyard: Spacious Chatham Retreat
The 3-bedroom Ping-Pong & Backyard: Spacious Chatham Retreat villa hosts up to 8 guests and is nestled 2.6 km from natural sites such as the Ridgevale Beach. Located around 10 minutes' drive from the Chatham Shark Center, this property provides Wi-Fi and private parking.
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Beach access
Cozy Cape Time
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Spa & wellness centre
- Garden area
Cozy Cape Time Villa Chatham is located approximately 10 minutes' drive from the family-friendly Oyster Pond Beach and provides horseback riding and fishing for active guests.
Cozy Cape Time
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Spa & wellness centre
- Garden area
Cozy Cape Time
Cozy Cape Time Villa Chatham is located approximately 10 minutes' drive from the family-friendly Oyster Pond Beach and provides horseback riding and fishing for active guests.
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Beach access
Charming Updated Home In Chatham
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
During the stay at Charming Updated Home In Chatham, guests can indulge in fishing or visit the Cockle Cove Beach, located 2.9 km away.
Charming Updated Home In Chatham
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Charming Updated Home In Chatham
During the stay at Charming Updated Home In Chatham, guests can indulge in fishing or visit the Cockle Cove Beach, located 2.9 km away.
Chatham Vacation Rentals with Private Pool
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Beach access
Wrap-Around Porch Mins To Beach
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
With the capacity to host 6 guests, the 2-bedroom Wrap-Around Porch Mins To Beach Chatham villa is located approximately a 15-minute ride from such significant cultural landmarks as the Atwood House & Museum. The accommodation features opportunities for fishing in the area, within a 6-km distance of the Chatham Railroad Museum.
Guests can benefit from barbecue offered in a private garden.
Wrap-Around Porch Mins To Beach
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Wrap-Around Porch Mins To Beach
With the capacity to host 6 guests, the 2-bedroom Wrap-Around Porch Mins To Beach Chatham villa is located approximately a 15-minute ride from such significant cultural landmarks as the Atwood House & Museum. The accommodation features opportunities for fishing in the area, within a 6-km distance of the Chatham Railroad Museum.
Guests can benefit from barbecue offered in a private garden.
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Beach access
Lucky Number Seven
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Spa & wellness centre
- Garden area
Lucky Number Seven Villa Chatham is located nearly a 25-minute walk from the family-friendly Oyster Pond Beach and provides fishing for active guests.
Lucky Number Seven
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Spa & wellness centre
- Garden area
Lucky Number Seven
Lucky Number Seven Villa Chatham is located nearly a 25-minute walk from the family-friendly Oyster Pond Beach and provides fishing for active guests.
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Beach access
Riviera Sunset
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Sun loungers
Riviera Sunset Villa Chatham is located about 25 minutes' walk from the Chatham Railroad Museum and provides fishing for active guests.
Riviera Sunset
- BBQ facilities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
- Sun loungers
Riviera Sunset
Riviera Sunset Villa Chatham is located about 25 minutes' walk from the Chatham Railroad Museum and provides fishing for active guests.
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Beach access
Lovely Home Near Bike Path Dog Welcome!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
The 4-bedroom Lovely Home Near Bike Path Dog Welcome! Chatham is located approximately a 25-minute walk from the Chase Park and provides fishing for active guests. Located 3.1 km from Chatham Light Beach, this 2-bathroom villa provides high-speed Internet access and private car parking.
Lovely Home Near Bike Path Dog Welcome!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Lovely Home Near Bike Path Dog Welcome!
The 4-bedroom Lovely Home Near Bike Path Dog Welcome! Chatham is located approximately a 25-minute walk from the Chase Park and provides fishing for active guests. Located 3.1 km from Chatham Light Beach, this 2-bathroom villa provides high-speed Internet access and private car parking.
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Beach access
Stellar Home With Hot Tub & Movie Room
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Jacuzzi
- Garden area
Located a mere 5 minutes' walk from the Maps of Antiquity, Stellar Home With Hot Tub & Movie Room Chatham is suitable for 10 guests and provides a Jacuzzi for a truly relaxing stay. This 4-bedroom villa features opportunities for fishing in the area, about 2 km from the Stage Harbor.
Stellar Home With Hot Tub & Movie Room
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Jacuzzi
- Garden area
Stellar Home With Hot Tub & Movie Room
Located a mere 5 minutes' walk from the Maps of Antiquity, Stellar Home With Hot Tub & Movie Room Chatham is suitable for 10 guests and provides a Jacuzzi for a truly relaxing stay. This 4-bedroom villa features opportunities for fishing in the area, about 2 km from the Stage Harbor.
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Beach access
Steps To Oyster Pond Private Dock!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Sun loungers
Steps To Oyster Pond Private Dock! Villa Chatham is located 3.5 km from the Cockle Cove Beach and provides fishing for active guests. Located just near the Oyster Pond, this 3-bathroom villa provides high-speed Internet access and private parking.
Steps To Oyster Pond Private Dock!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Sun loungers
Steps To Oyster Pond Private Dock!
Steps To Oyster Pond Private Dock! Villa Chatham is located 3.5 km from the Cockle Cove Beach and provides fishing for active guests. Located just near the Oyster Pond, this 3-bathroom villa provides high-speed Internet access and private parking.
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Beach access
Central Ac Close To Beach Dog Friendly!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Offering access to entertainment venues such as the Wharfinger Chatham Fish Pier, situated nearly a 10-minute drive away, the 3-bedroom Central Ac Close To Beach Dog Friendly! Chatham villa can host up to 8 guests. The Chatham holiday home features opportunities for fishing in the area, 3.1 km from the Ridgevale Beach.
Central Ac Close To Beach Dog Friendly!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
Central Ac Close To Beach Dog Friendly!
Offering access to entertainment venues such as the Wharfinger Chatham Fish Pier, situated nearly a 10-minute drive away, the 3-bedroom Central Ac Close To Beach Dog Friendly! Chatham villa can host up to 8 guests. The Chatham holiday home features opportunities for fishing in the area, 3.1 km from the Ridgevale Beach.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chatham, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Oyster Beach Bungalow |
8.1 / 10 (13 Reviews) |
From 125$ | |
| Updated Beach House Deck Outdoor Shower! |
9.8 / 10 (8 Reviews) |
From 678$ | |
| Sea House |
9.1 / 10 (13 Reviews) |
From 630$ | |
| Full Renovation Amazing Spot With Views |
9.6 / 10 (15 Reviews) |
From 782$ | |
| Pond Front Home W Game Room Dog Friendly |
9.2 / 10 (6 Reviews) |
From 357$ |
Frequently Asked Questions
Which vacation rentals in Chatham are pet-friendly?
You can find several pet-friendly options like the Central AC Close To Beach and Lovely Home Near Bike Path. These rentals welcome dogs and offer easy access to outdoor activities.
Book during weekdays to find the best rates, as many rentals offer discounts for extended stays.
What are the best vacation rentals near the beach in Chatham?
The Oyster Beach Bungalow and the Updated Beach House Deck Outdoor Shower! are both just a short walk from the beach. Enjoy the sun and surf while staying close to your rental.
Arrive early for beach access to avoid crowds, especially on weekends during summer.
Are there any vacation rentals in Chatham with a hot tub?
Stellar Home With Hot Tub & Movie Room offers a hot tub for relaxing after a day of fun. It's a great place to unwind.
Consider visiting during the off-season to benefit from lower prices and more availability.
Where can I find vacation rentals in Chatham with a view?
The Full Renovation Amazing Spot With Views offers stunning scenery. Enjoy watching the sunset from the comfort of your rental.
Book a few months in advance during peak season to secure a rental with the best views.
Which vacation rentals in Chatham are suitable for families?
Consider the Cozy Cape Time and the Wrap-Around Porch Mins To Beach for family-friendly amenities. Both rentals are spacious and close to family activities.
Plan activities around nearby attractions like the Chatham Lighthouse Beach for family fun.
What vacation rentals in Chatham have two bedrooms?
The Charming Updated Home In Chatham and the Pond Front Home W Game Room offer two-bedroom options. These are perfect for small families or groups.
Check availability before summer starts, as two-bedroom rentals often book quickly.
Are there all-inclusive vacation rentals in Chatham?
While typical vacation rentals do not offer all-inclusive packages, some may include amenities like breakfast. Look at options like the Stellar Home With Hot Tub & Movie Room for extra conveniences.
Confirm what's included in your rental to avoid surprises upon arrival.
What is the best time to visit Chatham for vacation rentals?
Late spring to early fall offers the best weather and many local festivals. Plan your vacation around events like the Chatham Fish Pier's annual fish fry to experience local culture.
Visit in early June for lower rental prices and fewer crowds while still enjoying pleasant weather.
How can I find the best deals on vacation rentals in Chatham?
Consider booking during the shoulder seasons, like before or after summer. After Labor Day, rates drop significantly and rentals are more available.
Stay mid-week to find better deals as it's less crowded on weekdays.
What activities should I plan while staying at vacation rentals in Chatham?
Chatham offers beautiful beaches, hiking trails, and local dining options. Visiting places like the Monomoy National Wildlife Refuge and enjoying a boat tour will enhance your visit.
Check out local events like the Chatham Harbor 5K for fun community involvement during your stay.