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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: 13

Chatham
Chatham Walk to Hardings Beach Spectacular Oceanview House
5BR
4 ½ baths
Sleeps 10

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

Contact: Wendy Gruenberg, Property ID: 16695
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
Ridgevale-Walk to Beach-pets considered-spacious home
4BR
2 baths
Sleeps 9

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
4 Bedroom Air Conditioned Home 1 Mile from Beach
4BR
3 ½ baths
Sleeps 8

September thru May is available

Contact: Ferraro Nancy, Property ID: 28617
Charming Family Cape, Impeccably Landscaped With Ocean Views
3BR
2 baths
Sleeps 8

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

Contact: Justin, Property ID: 38971
Blue Hydrangea Cottage
3BR
3 baths
Sleeps 6

Will rent monthly between September and May. Will discuss rate depending on number of occupants. Your range could be between 3,000-3,500.

Contact: Heather A. Dean, Property ID: 34674
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
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
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
Oceanfront Holiday Shores, Seaside Cottage, South Chatham MA
2BR
1 bath
Sleeps 5

Available off season for $1000 per week April 21 - June 16 September 5 - Nov. 17

Contact: Pam Parsons, Property ID: 13850
Charming Chatham Cottage w/AC - Walk to town and beach
2BR
1 bath
Sleeps 4

Winter rental! $2,150/mo This furnished cottage is available September through June! Perfect for a single person or a couple. Includes: heat, hot wate...

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

The cottage is available in the off-season Oct. - May as a monthly rental for $1000/mo. All utilities included.

Contact: Carol, Property ID: 30589