Chatham Vacation Rentals
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Chatham, MA
Book a vacation rental in Chatham that has the highest visitor rating. Here are 6 of the best vacation rentals in Chatham.
3-Bedroom Oceanfront Cottage with Private Beach
10
Excellent
·
Apartment
·
3 br
·
Sleeps 8
·
Beach · Roof Deck · Residents Lounge ·
From
$665/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Beach
Roof Deck
Residents Lounge
Ocean
Waterfront
Wifi
Furnished
Oven
Other spaces
Kitchen
Price drop
Oceanview Brewster Home
10
Excellent
·
House
·
4 br
·
Sleeps 10
·
Oven · High Ceilings · Air Conditioning ·
From
$431/nightProperty
House · 4 Beds · 4 baths
Amenities
Oven
High Ceilings
Air Conditioning
Hardwood Floor
In Unit Laundry
Furnished
Dishwasher
Wifi
Other spaces
Balcony, Kitchen
Booking Summer ‘23! Pvt rd. to Great Pond. Steps to bike path. 100% renovated!
10
Excellent
·
House
·
2 br
·
Sleeps 4
·
Furnished · Hardwood Floor · Kitchen ·
From
$213/nightProperty
House · 2 Beds · 1 bath
Amenities
Furnished
Hardwood Floor
Fitness Center
In Unit Laundry
Air Conditioning
Fireplace
Oven
Dishwasher
Other spaces
Kitchen
Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
10
Excellent
·
Apartment
·
2 br
·
Sleeps 5
·
Air Conditioning · Kitchen · Wifi ·
From
$150/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
Wifi
In Unit Laundry
Beach
Oven
Furnished
Fitness Center
Residents Lounge
Other spaces
Kitchen
Price drop
Steps to popular South Village Beach!! 5 Bedroom home sleeping 10!
10
Excellent
·
House
·
5 br
·
Sleeps 10
·
Wifi · Furnished · Dishwasher ·
From
$285/nightProperty
House · 5 Beds · 3 baths
Amenities
Wifi
Furnished
Dishwasher
Air Conditioning
Fitness Center
Oven
In Unit Laundry
Other spaces
Kitchen
Dog friendly home w/ deck and private gas grill - on the bay side of the Cape!
10
Excellent
·
House
·
3 br
·
Sleeps 8
·
Outdoor Space · Dishwasher · Furnished ·
From
$142/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
Furnished
In Unit Laundry
Air Conditioning
Free Parking
Oven
On Site Laundry
Wifi
Other spaces
Kitchen
Budget-Friendly Vacation Rentals in Chatham, MA
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chatham starting at $1. Use the price filter at the top of the page to search for more specific prices.
Price drop
This B-Style Billington Village townhouse has access to Golf and Pool. (Fees Apply)
No rating
·
House
·
1 br
·
Sleeps 6
·
Fitness Center · Kitchen · Wifi ·
From
$1/nightProperty
House · 1 Bed · 2 baths
Amenities
Fitness Center
Wifi
Furnished
Air Conditioning
Pool
Oven
In Unit Laundry
Swimming Pool
Other spaces
Kitchen
Price drop
14472: Cozy, Colorful Cottage, Perfect for 2! Near Drive-In Theater, 4 Mins to Bayside Beaches!
4
Good
·
Apartment
·
1 br
·
Sleeps 2
·
Air Conditioning · Kitchen · Furnished ·
From
$44/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Wifi
Residents Lounge
Other spaces
Kitchen
Price drop
Quaint condo near private beach access with fireplace - close to dining
10
Excellent
·
Condo
·
1 br
·
Sleeps 4
·
Air Conditioning · In Unit Laundry · Dishwasher ·
From
$49/nightProperty
Condo · 1 Bed · 2 baths
Amenities
Air Conditioning
In Unit Laundry
Dishwasher
Beach
Fireplace
Furnished
Wifi
Roof Deck
Other spaces
Kitchen
Price drop
Dreamy Cottage for Two! Close to Beaches!
10
Excellent
·
Apartment
·
1 br
·
Sleeps 2
·
Outdoor Space · Wifi · Furnished ·
From
$50/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Air Conditioning
Other spaces
Kitchen
Price drop
4 Min Drive to Bayside Beaches!
10
Excellent
·
Apartment
·
1 br
·
Sleeps 2
·
Kitchen · Wifi · Furnished ·
From
$53/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Residents Lounge
Air Conditioning
Other spaces
Kitchen
New August discounted rate -2 bed condo, private beach, pool, tennis, and dining
10
Excellent
·
Condo
·
2 br
·
Sleeps 4
·
Oven · Air Conditioning · Dishwasher ·
From
$59/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Oven
Air Conditioning
Dishwasher
Furnished
Assigned Parking
Waterfront
In Unit Laundry
Fitness Center
Other spaces
Kitchen
Vacation Rentals With A Pool in Chatham, MA
Want to relax by the pool? Book one of these Chatham vacation rentals with a pool.
Private Orleans resort with water views, heated pool/spa & fire pit: 009-O
10
Excellent
·
House
·
4 br
·
Sleeps 14
·
High Ceilings · Kitchen · Air Conditioning ·
From
$1,502/nightProperty
House · 4 Beds · 5 baths
Amenities
High Ceilings
Air Conditioning
Dishwasher
Fireplace
Residents Lounge
Hot Tub
Walk In Closets
Furnished
Other spaces
Kitchen, Balcony, Deck
Price drop
Bluebird Dennisport
7.9
Very good
·
Hotel
·
1 br
·
Sleeps 4
·
Furnished · Residents Lounge · Assigned Parking ·
From
$230/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Residents Lounge
Assigned Parking
Wheelchair Accessible
Air Conditioning
Storage
On Site Laundry
Swimming Pool
Price drop
Brand New Luxury Home with Heated Pool, Walk to Rock Harbor: 076-O
No rating
·
House
·
4 br
·
Sleeps 10
·
Residents Lounge · Garage Parking · Hot Tub ·
From
$965/nightProperty
House · 4 Beds · 5 baths
Amenities
Residents Lounge
Garage Parking
Hot Tub
Wifi
Pool
Private Pool
Swimming Pool
Fireplace
Other spaces
Kitchen
Vacation Rentals With AC and/or Heat in Chatham, MA
Whether you need air conditioning or central heating, these vacation rentals are for you.
Cape House in Yarmouth w/ Private Hot Tub + Kayaks
No rating
·
House
·
1 br
·
Sleeps 4
·
Air Conditioning · Kitchen · Outdoor Space ·
From
$216/nightProperty
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Central Heat
Hot Tub
In Unit Laundry
Oven
Furnished
Other spaces
Kitchen
Price drop
Scargo Vista ~ Professionally designed, Completely renovated craftsman home
10
Excellent
·
House
·
4 br
·
Sleeps 10
·
Furnished · Central Heat · Garage Parking ·
From
$475/nightProperty
House · 4 Beds · 5 baths
Amenities
Furnished
Central Heat
Garage Parking
Wifi
Fireplace
Dishwasher
Oven
Hot Tub
Other spaces
Kitchen
Price drop
Tranquil Cape house with private backyard, deck, grill, & enclosed porch
10
Excellent
·
House
·
4 br
·
Sleeps 8
·
Air Conditioning · Dishwasher · In Unit Laundry ·
From
$393/nightProperty
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
In Unit Laundry
On Site Laundry
Free Parking
Oven
Furnished
Central Heat
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals.
Updated: September 30, 2023
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