Chatham, MA holiday rentals

Vacation Rentals in Chatham, MA

1173 available vacation rental offers

2 1
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1173 Holiday rentals and Airbnb in Chatham, MA

Charming & Clean Chatham Guest Suite - Chatham, MA
9.9Excellent 54 reviews
Chatham, MA
2 1
A$449/nighttotal: A$1347 (3 )

Charming & Clean Chatham Guest Suite

studio
Chatham
About Charming & Clean Chatham Guest Suite

About: Holiday rental listing for up to 3 people with an excellent rating of 99% based on 54 reviews. You will be based in Chatham.

Facilities and services include a barbecue, a garden and a fridge.

Chatham Village - Center - Main Street Center Area - Chatham, MA
9.8Excellent 112 reviews
Chatham, MA
2 3
A$701/nighttotal: A$2103 (3 )

Chatham Village - Center - Main Street Center Area

apartment
Chatham
About Chatham Village - Center - Main Street Center Area

About: Apartment listing for up to 6 guests with an excellent rating of 98% based on 112 reviews. You will be in Chatham.

Facilities and services include a pool table, a fridge and a terrace.

Lovely Home Minutes From Beach In Chatham! - Chatham, MA
9.4Excellent 110 reviews
Chatham, MA
2 3
A$735/nighttotal: A$2205 (3 )

Lovely Home Minutes From Beach In Chatham!

apartment
Chatham
About Lovely Home Minutes From Beach In Chatham!

About: Holiday rental listing for 6 guests with an excellent rating of 94% based on 110 reviews. You will stay in Chatham.

Services and facilities: a kitchen, an iron and free parking. This apartment in Chatham also has a garden!

South Chatham Sunshine - Chatham, MA
9.5Excellent 141 reviews
Chatham, MA
2 3
A$640/nighttotal: A$1920 (3 )

South Chatham Sunshine

house
Chatham
About South Chatham Sunshine

About: Accommodation from 192 dollars per night for up to 6 people with an excellent rating of 95% based on 141 reviews. This accommodation is located in Chatham.

Services and facilities include a washing machine, a garden and a fridge. Take advantage of the terrace in this house in Chatham.

Pleasant Bay Village Resort - Standard Room - Chatham, MA
9.4Excellent 516 reviews
Chatham, MA
2 1
A$510/nighttotal: A$1530 (3 )

Pleasant Bay Village Resort - Standard Room

B&B
Chatham
About Pleasant Bay Village Resort - Standard Room

About: B&B with an excellent rating of 94% based on 516 reviews. Your accommodation will be located in Chatham.

Services and facilities: a ping pong table, a business center and air conditioning. This accommodation in Chatham also has a gym!

Chatham 3 Bedroom/2 Bath Retreat - Chatham, MA
8.8Very good 78 reviews
Chatham, MA
2 3
A$705/nighttotal: A$2115 (3 )

Chatham 3 Bedroom/2 Bath Retreat

apartment
Chatham
About Chatham 3 Bedroom/2 Bath Retreat

About: Holiday rental listing with an excellent rating of 88% based on 78 reviews. You will be located in Chatham.

Facilities and services include a kitchen, a dish washer and a terrace. This apartment also has a garden!

Wrap-around Porch Mins. To Beach! - Chatham, MA
9.7Excellent 67 reviews
Chatham, MA
2 2
A$563/nighttotal: A$1689 (3 )

Wrap-around Porch Mins. To Beach!

apartment
Chatham
About Wrap-around Porch Mins. To Beach!

About: Apartment for 6 people with an excellent rating of 97% based on 67 reviews. You will be based in Chatham.

Facilities and services include a freeze, a terrace and a fridge. Take advantage of the garden in this apartment!

Charming Walk To Beach Chatham-bayview Beach House--central A/c; Wi-fi - Chatham, MA
9.8Excellent 86 reviews
Chatham, MA
2 3
A$689/nighttotal: A$2067 (3 )

Charming Walk To Beach Chatham-bayview Beach House--central A/c; Wi-fi

house
Chatham
About Charming Walk To Beach Chatham-bayview Beach House--central A/c; Wi-fi

About: Accommodation with an excellent rating of 98% based on 86 reviews. You will be located in Chatham.

Services and facilities: a fitness center, air conditioning and a child space. This house in Chatham also has a garden!

Kid-friendly Ridgevale Beach Is An Easy Stroll From This Comfy Beach House! - Chatham, MA
10Excellent 5 reviews
Chatham, MA
2 3
A$662/nighttotal: A$1986 (3 )

Kid-friendly Ridgevale Beach Is An Easy Stroll From This Comfy Beach House!

house
Chatham
About Kid-friendly Ridgevale Beach Is An Easy Stroll From This Comfy Beach House!

About: Holiday rental from 362 dollars per night for 7 guests with an excellent rating of 100% based on 5 reviews. Your accommodation will be located in Chatham.

Services and facilities: free parking, a washing machine and air conditioning.

Renovated Cottage 1 Mile To Beach In Chatham! - Chatham, MA
9.7Excellent 66 reviews
Chatham, MA
2 2
A$552/nighttotal: A$1656 (3 )

Renovated Cottage 1 Mile To Beach In Chatham!

cottage
Chatham
About Renovated Cottage 1 Mile To Beach In Chatham!

About: Cottage at 321 dollars for 4 people with an excellent rating of 97% based on 66 reviews. This accommodation is based in Chatham.

Services and facilities: a fridge, air conditioning and free parking.

"Chatham Up" - Come Stay, Relax, Have Fun! - Chatham, MA
8.7Very good 56 reviews
Chatham, MA
2 2
A$610/nighttotal: A$1830 (3 )

"Chatham Up" - Come Stay, Relax, Have Fun!

apartment
Chatham
About "Chatham Up" - Come Stay, Relax, Have Fun!

About: Holiday rental for 5 people with an excellent rating of 87% based on 56 reviews. This accommodation is located in Chatham.

Facilities and services: a cleaning service, a kitchen and a washing machine. Take advantage of the gym in this apartment in Chatham.

The Captain Kimball House Of Christmas Joy - Chatham, MA
9.9Excellent 138 reviews
Chatham, MA
2 2
A$464/nighttotal: A$1392 (3 )

The Captain Kimball House Of Christmas Joy

Chatham
About The Captain Kimball House Of Christmas Joy

About:

Other types of accommodation in Chatham, MA

Best Chatham, MA holiday rentals with a pool

Among the 1173 accommodations in Chatham, MA, here are the 8 best rentals with a pool

Wequassett Resort and Golf Club - Chatham, MA
9.3Excellent 225 reviews
Chatham, MA
2 1
A$1428/nighttotal: A$4284 (3 )

Wequassett Resort and Golf Club

resort
Harwich
About Wequassett Resort and Golf Club

About: Vacation resort listing with an excellent rating of 93% based on 225 reviews. This accommodation is located in Harwich.

Services and facilities include newspapers, a cleaning service and a room service. This is a pet-friendly resort!

Updated Chatham Inn Home | Spacious Deck & Private Heated Pool - Chatham, MA
9.3Excellent 78 reviews
Chatham, MA
2 5
A$1062/nighttotal: A$3186 (3 )

Updated Chatham Inn Home | Spacious Deck & Private Heated Pool

hotel
Chatham
About Updated Chatham Inn Home | Spacious Deck & Private Heated Pool

About: Room with an excellent rating of 93% based on 78 reviews. This accommodation is based in Chatham.

Facilities and services include a dish washer, a washing machine and a terrace. Take advantage of the air conditioning in this hotel!

Updated Chatham Family Compound, Heated Pool & Hot Tub, 489-c - Chatham, MA
9.9Excellent 15 reviews
Chatham, MA
2 4
A$2658/nighttotal: A$7974 (3 )

Updated Chatham Family Compound, Heated Pool & Hot Tub, 489-c

apartment
Chatham
About Updated Chatham Family Compound, Heated Pool & Hot Tub, 489-c

About: Accommodation from 2544 dollars per night for 14 people with an excellent rating of 99% based on 15 reviews. This accommodation is located in Chatham.

Services and facilities include air conditioning, a washing machine and a barbecue. Enjoy a swimming pool in this apartment in Chatham!

Private Heated Pool! Pet Friendly, Sleeps 9 Near The Beach! - Chatham, MA
10Excellent 3 reviews
Chatham, MA
2 4
A$3235/nighttotal: A$9705 (3 )

Private Heated Pool! Pet Friendly, Sleeps 9 Near The Beach!

apartment
Chatham
About Private Heated Pool! Pet Friendly, Sleeps 9 Near The Beach!

About: Apartment listing with an excellent rating of 100% based on 3 reviews. You will be in Chatham.

Services and facilities: a terrace, a kitchen and an iron. Enjoy free parking with this accommodation in Chatham!

Luxury 7 Br, 4 Ba W/ Unique 60 Ft Pool, .4 Miles To Beach - Chatham, MA
9.8Excellent 73 reviews
Chatham, MA
2 7
A$2675/nighttotal: A$8025 (3 )

Luxury 7 Br, 4 Ba W/ Unique 60 Ft Pool, .4 Miles To Beach

apartment
Orleans
About Luxury 7 Br, 4 Ba W/ Unique 60 Ft Pool, .4 Miles To Beach

About: Holiday rental listing for 16 guests with an excellent rating of 98% based on 73 reviews. Your accommodation will be based in Orleans.

Services and facilities include a garden, a fridge and a fitness center.

Walk To Beach, Heated Pool, Ac, Wifi, Modern Coastal Decor, Dog Friendly - Chatham, MA
9.7Excellent 7 reviews
Chatham, MA
2 3
A$3959/nighttotal: A$11877 (3 )

Walk To Beach, Heated Pool, Ac, Wifi, Modern Coastal Decor, Dog Friendly

apartment
Chatham
About Walk To Beach, Heated Pool, Ac, Wifi, Modern Coastal Decor, Dog Friendly

About: Apartment listing from A$2847 for up to 10 people with an excellent rating of 97% based on 7 reviews. You will stay in Chatham.

Facilities and services: a washing machine, a tennis court and a fridge. This apartment in Chatham has a swimming pool!

Cape Springs Cottage - Chatham, MA
Chatham, MA
2 1
A$1465/nighttotal: A$4395 (3 )

Cape Springs Cottage

house
Chatham
About Cape Springs Cottage

About: Holiday house to rent. You will be located in Chatham.

Facilities and services include a swimming pool, air conditioning and a fridge. This house is ideal for families.

93 Bucks Creek Road Chatham Cape Cod - - Coastal Charm - Chatham, MA
Chatham, MA
2 4
A$4064/nighttotal: A$12192 (3 )

93 Bucks Creek Road Chatham Cape Cod - - Coastal Charm

house
Chatham
About 93 Bucks Creek Road Chatham Cape Cod - - Coastal Charm

About: House for up to 10 guests. Your accommodation will be located in Chatham.

Facilities and services include a dish washer, free parking and a barbecue. Take a dip in the pool of this house in Chatham!

Best family friendly Chatham, MA holiday rentals

Among the 1173 accommodations in Chatham, MA, here are the 8 best family friendly rentals

Chatham Beach Chic 5 ⭐ 5min's Walk To Private Beach-newly Renov'd Family Retreat - Chatham, MA
10Excellent 162 reviews
Chatham, MA
2 4
A$1191/nighttotal: A$3573 (3 )

Chatham Beach Chic 5 ⭐ 5min's Walk To Private Beach-newly Renov'd Family Retreat

apartment
Chatham
About Chatham Beach Chic 5 ⭐ 5min's Walk To Private Beach-newly Renov'd Family Retreat

About: Holiday rental listing for 10 people with an excellent rating of 100% based on 162 reviews. Your accommodation will be based in Chatham.

Facilities and services include air conditioning, a tennis court and a kitchen. Enjoy a gym in this apartment in Chatham!

Cape Cod Home with Fire Pit & Grills - Near Beaches! - Chatham, MA
9.4Excellent 67 reviews
Chatham, MA
2 1
A$1014/nighttotal: A$3042 (3 )

Cape Cod Home with Fire Pit & Grills - Near Beaches!

house
Chatham
About Cape Cod Home with Fire Pit & Grills - Near Beaches!

About: House rental listing from A$548 per night for up to 10 guests with an excellent rating of 94% based on 67 reviews. You will be based in Chatham.

Services and facilities include an iron, free parking and a dish washer. This is a pet-friendly accommodation!

5 Bed/2 Bath Sleeps 11. Walk To Restaurants, Town And More... - Chatham, MA
9.8Excellent 59 reviews
Chatham, MA
2 5
A$1359/nighttotal: A$4077 (3 )

5 Bed/2 Bath Sleeps 11. Walk To Restaurants, Town And More...

cottage
Chatham
About 5 Bed/2 Bath Sleeps 11. Walk To Restaurants, Town And More...

About: Cottage rental from 1001 dollars for 11 people with an excellent rating of 98% based on 59 reviews. This accommodation is based in Chatham.

Services and facilities include a kitchen, a washing machine and a fridge. Take advantage of the garden in this accommodation in Chatham.

Harwich Tranquility - Chatham, MA
9.3Excellent 61 reviews
Chatham, MA
2 1
A$548/nighttotal: A$1644 (3 )

Harwich Tranquility

house
Harwich
About Harwich Tranquility

About: House rental from A$352 for 6 people with an excellent rating of 93% based on 61 reviews. You will be based in Harwich.

Services and facilities include a wheelchair friendly access, a fridge and free parking. Take advantage of the air conditioning in this house!

Oyster Pond Newly Renovated Open Floor Plan - Chatham, MA
10Excellent 137 reviews
Chatham, MA
2 3
A$1388/nighttotal: A$4164 (3 )

Oyster Pond Newly Renovated Open Floor Plan

apartment
Chatham
About Oyster Pond Newly Renovated Open Floor Plan

About: Apartment with an excellent rating of 100% based on 137 reviews. This accommodation is based in Chatham.

Facilities and services include a garden, a child space and a fitness center. Take advantage of the terrace in this apartment in Chatham.

Chatham Preservation Award: Antique Cape In Chatham Center - Chatham, MA
10Excellent 18 reviews
Chatham, MA
2 3
A$953/nighttotal: A$2859 (3 )

Chatham Preservation Award: Antique Cape In Chatham Center

apartment
Chatham
About Chatham Preservation Award: Antique Cape In Chatham Center

About: Accommodation from 789 dollars for 6 people with an excellent rating of 100% based on 18 reviews. You will be in Chatham.

Services and facilities include a spa, free parking and a washing machine. Take advantage of the terrace in this apartment in Chatham.

Historic Waterfront Home With Sweeping Chatham Water Views! Pet Friendly! - Chatham, MA
10Excellent 72 reviews
Chatham, MA
2 4
A$1711/nighttotal: A$5133 (3 )

Historic Waterfront Home With Sweeping Chatham Water Views! Pet Friendly!

apartment
Chatham
About Historic Waterfront Home With Sweeping Chatham Water Views! Pet Friendly!

About: Holiday rental listing with an excellent rating of 100% based on 72 reviews. Your accommodation will be based in Chatham.

Services and facilities include a washing machine, a terrace and an iron. Take advantage of the garden in this apartment in Chatham.

Unique Family Gathering Place ,Bright, Spacious. Linens Included - Chatham, MA
9.9Excellent 95 reviews
Chatham, MA
2 5
A$1736/nighttotal: A$5208 (3 )

Unique Family Gathering Place ,Bright, Spacious. Linens Included

house
Chatham
About Unique Family Gathering Place ,Bright, Spacious. Linens Included

About: Holiday house rental for 10 people with an excellent rating of 99% based on 95 reviews. This accommodation is based in Chatham.

Services and facilities include air conditioning, a dish washer and a barbecue. This house in Chatham is ideal for families.

Frequently asked questions for the holiday rentals in Chatham, MA

Destinations nearby

Best pet friendly Chatham, MA holiday rentals

Among the 1173 accommodations in Chatham, MA, here are the 8 best pet friendly rentals

On Goose Pond Pet Friendly Wifi Water Views Private - Chatham, MA
10Excellent 14 reviews
Chatham, MA
2 1
A$712/nighttotal: A$2136 (3 )

On Goose Pond Pet Friendly Wifi Water Views Private

cottage
Chatham
About On Goose Pond Pet Friendly Wifi Water Views Private

About: Cottage listing from 426 dollars for 4 people with an excellent rating of 100% based on 14 reviews. You will be located in Chatham.

Services and facilities include a spa, free parking and a massage service.

This Lovely Condo Location In Town, Has Both A Brick Patio And Deck For You To Enjoy Your Morning Coffee On! - Chatham, MA
9.3Excellent 2 reviews
Chatham, MA
2 1
A$771/nighttotal: A$2313 (3 )

This Lovely Condo Location In Town, Has Both A Brick Patio And Deck For You To Enjoy Your Morning Coffee On!

apartment
Chatham
About This Lovely Condo Location In Town, Has Both A Brick Patio And Deck For You To Enjoy Your Morning Coffee On!

About: Apartment with an excellent rating of 93% based on 2 reviews. Your accommodation will be based in Chatham.

Services and facilities: a garden, a kitchen and a washing machine. Take advantage of the Free Parking with this accommodation.

Historic 1799 Retreat, Walk To Beach And Dining - Chatham, MA
9.5Excellent 164 reviews
Chatham, MA
2 2
A$469/nighttotal: A$1407 (3 )

Historic 1799 Retreat, Walk To Beach And Dining

apartment
Chatham
About Historic 1799 Retreat, Walk To Beach And Dining

About: Holiday rental listing for 5 guests with an excellent rating of 95% based on 164 reviews. You will be in Chatham.

Facilities and services: a garden, a washing machine and an iron. Take advantage of the air conditioning in this apartment in Chatham.

Deeded Rights To Emery Pond Fire Pit! - Chatham, MA
9.6Excellent 85 reviews
Chatham, MA
2 3
A$763/nighttotal: A$2289 (3 )

Deeded Rights To Emery Pond Fire Pit!

apartment
Chatham
About Deeded Rights To Emery Pond Fire Pit!

About: Holiday rental for 6 guests with an excellent rating of 96% based on 85 reviews. Your accommodation will be based in Chatham.

Facilities and services: an iron, a barbecue and a freeze. This apartment in Chatham also has a garden!

Chatham Hideaway Near Cockle Cove Beach! - Chatham, MA
10Excellent 43 reviews
Chatham, MA
2 1
A$632/nighttotal: A$1896 (3 )

Chatham Hideaway Near Cockle Cove Beach!

cottage
Chatham
About Chatham Hideaway Near Cockle Cove Beach!

About: Cottage listing for up to 7 guests with an excellent rating of 100% based on 43 reviews. You will be in Chatham.

Services and facilities: a garden, a washing machine and a fridge.

Beautiful Home W/ Artistic Flair! - Chatham, MA
9.6Excellent 10 reviews
Chatham, MA
2 3
A$861/nighttotal: A$2583 (3 )

Beautiful Home W/ Artistic Flair!

apartment
Chatham
About Beautiful Home W/ Artistic Flair!

About: Holiday rental for 7 guests with an excellent rating of 96% based on 10 reviews. You will stay in Chatham.

Services and facilities: free parking, a freeze and a washing machine. Take advantage of the terrace in this apartment!

Lovely Updated Cape Home 1 Mile To Beach! - Chatham, MA
9.2Excellent 42 reviews
Chatham, MA
2 2
A$536/nighttotal: A$1608 (3 )

Lovely Updated Cape Home 1 Mile To Beach!

apartment
Chatham
About Lovely Updated Cape Home 1 Mile To Beach!

About: Apartment to rent for 4 guests with an excellent rating of 92% based on 42 reviews. Your accommodation will be based in Chatham.

Services and facilities include a freeze, a barbecue and free parking. Take advantage of the air conditioning in this apartment!

Chatham Charmer - Chatham, MA
9.7Excellent 14 reviews
Chatham, MA
2 3
A$930/nighttotal: A$2790 (3 )

Chatham Charmer

house
Chatham
About Chatham Charmer

About: Holiday house rental for 7 people with an excellent rating of 97% based on 14 reviews. Your accommodation will be located in Chatham.

Services and facilities include a dish washer, a barbecue and an ATM. Take advantage of the Free Parking with this accommodation in Chatham!