Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.

Long-Term Vacation Rentals in Chatham

Rental homes are available for an extended stay of a month or more at a time. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring).

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 11

Chatham
True Waterfront 4 Bedrooms, 4 Acres on Nantucket Sound
4BR
2 baths
Sleeps 10

Possible. $3500 per month plus utilities

Contact: Harvey Ross, Property ID: 9648
Chatham Walk to Hardings Beach Spectacular Oceanview House
4BR
4 ½ baths
Sleeps 10

November, December, January, February, March, April. $6500 per month.

Contact: Wendy Gruenberg, Property ID: 16695
Secluded charming home off of Main Street/Walk to Beach
4BR
2 ½ baths
Sleeps 8

1 month or more $16,000

Contact: Courtney, Property ID: 39782
Ridgevale-Walk to Beach-pets considered-spacious home
3BR
2 baths
Sleeps 8

This house is available as a winter rental from mid October to mid May 2024, $1,650 per month plus utilities.

Contact: Paul K. McGrath, Property ID: 4560
Charming Family Cape, Impeccably Landscaped With Ocean Views
3BR
2 baths
Sleeps 8

$4000/mo. We welcome the opportunity to discuss off-season, long term rentals (October - May). Please reach out for more information should you be in...

Contact: Justin, Property ID: 38971
Value! Charming Chatham 3 Bedroom Home; Close to Town/Water
3BR
1 ½ bath
Sleeps 6

Sleeps 6 in 3 Bedrooms. Available approx November through May. $1400-$3500 monthly depending upon length of stay, plus utilities. Small pets considere...

Contact: Catherine Batcheller, Property ID: 20787
3BR nr Hardings Beach, 5 min walk Oyster River,see reviews!
3BR
2 baths
Sleeps 6

Available as a winter rental end of October to mid May. $1200-1500/ month plus utilities and security deposit.

Contact: Bob Sneden, Property ID: 23722
Newly Restored Cottage
3BR
2 ½ baths
Sleeps 6

The only months available for long term rents are Nov., Dec. Jan. Feb. March, April minimum rent $1600 month plus utilities

Contact: Joyce Anderson, Property ID: 25053
Location and View! Waterfront Cottage In Town
3BR
1 ½ bath
Sleeps 6

We would consider a 6 month rental (starting Oct/Nov). $20,000

Contact: Erin, Property ID: 28980
Chatham Charmer, Walk-to-Town & Beach!
2BR
1 bath
Sleeps 4

Off season in Chatham? Yes please! This cottage is a perfect fit for a single person or a couple looking to be in Chatham for the winter. $2,300/mo c...

Contact: Sean Pope, Property ID: 25326
Chatham Village cottage weekly summer rental 2nt off season
1BR
1 bath
Sleeps 3

The cottage is available for single occupancy only in the off-season Oct. - May as a monthly rental for $1200/mo. All utilities included.

Contact: Carol, Property ID: 30589