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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). Monthly prices may vary depending on the number in your party and length of stay.

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

# of Rentals: 10

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

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 or $1250-1500 weekly....

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