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Long-Term Vacation Rentals in Chatham

A long-term rental is considered to be an extended stay of more than 31 days. 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). Massachusetts Landlord Tenant Laws will apply.

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

# of Rentals: 18

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

Possible. $3500 per month plus utilities

Contact: Harvey Ross, ID: 9648
Hardings Beach Area Rental
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, ID: 16695
Chatham Rental
Windswept
4BR
2 baths
Sleeps 9

The rental can be rented for 32 nights or longer, if the calendar allows it... Stay longer and save the 14.45% rental tax!

Contact: Pine Acres Rentals, ID: 39991
Chatham Rental
Secluded charming home off of Main Street/Walk to Beach
4BR
2 ½ baths
Sleeps 8

1 month or more $16,000

Contact: Courtney, ID: 39782
Chatham Rental
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, ID: 38971
Chatham Rental
Spacious Family Home near Ridgevale Beach!
3BR
2 baths
Sleeps 8

Open to longer rentals, if the calendar allows.. Stay 32 nights or longer and save on the 14.45 rental tax!

Contact: Pine Acres Rentals, ID: 39993
Chatham Rental
Chatham Beach Chic 5 STAR Family retreat-5 min walk to Beach
3BR
2 baths
Sleeps 8

There is no 14.45% Lodging Tax for stays of 31 nights or more.

Contact: John Muldoon, ID: 24757
Chatham Rental
Views of Bucks Creek!
3BR
3 baths
Sleeps 8

If the calendar allows, the house can be rented for 32 nights or longer, book it and avoid the 14.45% short term rental tax

Contact: Karen at Pine Acres Rentals, ID: 40116
Chatham Rental
Private and Peaceful in the Heart of Chatham!
4BR
3 baths
Sleeps 7

Open to longer term rentals, if the calendar allows it.. Stay 32 nights or longer and save the 14.45% rental tax!

Contact: Pine Acres Rentals, ID: 39997
Chatham Rental
Charming Chatham Bungalow-Minutes to Downtown and Beaches
3BR
1 bath
Sleeps 7

We are always looking for off-season or longer term renters as well. Message us for longer term rentals so we can discuss the details. Average monthl...

Contact: Allison Warren, ID: 40064
S. Chatham Rental
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, ID: 25053
Chatham Rental
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, ID: 28980
Chatham Rental
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, ID: 20787
Chatham Rental
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, ID: 23722
Chatham Rental
Steps to Downtown Chatham and Lighthouse Beach
3BR
2 baths
Sleeps 5

The rental is open to rentals 32 nights or longer, if the calendar allows it. Save the Rental Tax and Stay Longer!

Contact: Pine Acres Rentals, ID: 39987
South Chatham Rental
OOHLAHLAH Charming, Cozy Cottage, Walk to Beach
2BR
2 baths
Sleeps 5

30-day minimum stay May 28-June 28, 2025 = $8000.00 June 28-July 26, 2025 = $10,000.00 July 26-August 30, 2025= $10,000.00 August 30-October 4 = $...

Contact: Allen, ID: 40037
Chatham Rental
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, ID: 25326
Chatham village Rental
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, ID: 30589