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Long-Term Vacation Rentals in Dennis

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: 13

Dennis
Dennis Port Rental
Main House and Adjoining Cottage - Great for Large Families
6BR
3 ½ baths
Sleeps 15

Available for Long-term winter rentals - Cottage is NOT included since it is not winterized Price range from $3,400 to 4,000

Contact: Kim, ID: 18302
Dennis Rental
Classic Cape Home. Walk to Mayflower & Bayview Beaches
4BR
2 baths
Sleeps 10

Available October - April $4,500-6,500/mo depending on length of stay

Contact: Leslie, ID: 41528
Dennis Rental
Pool + 4 Minute Walk to Beach in Heart of Dennisport!
4BR
1 ½ bath
Sleeps 10

We are open to long-term rental from October - May if interested! $3,000-$5000/mo

Contact: Regina, ID: 41772
Dennis Rental
Walk to Mayflower Beach & Restaurants
4BR
3 baths
Sleeps 9

Available from Oct 1st - May 31st 2027 - $3000 plus utilities - Ask about specifics

Contact: Joseph Boike, ID: 38453
Dennis Rental
Off season rental Oct - May also booking for summer 2027
4BR
1 ½ bath
Sleeps 8

10/2026 - 5/2027: Four-bedroom furnished home $2500/mo. Minimum 5 months. Dogs considered. I pay for internet & trash. You would be responsible for ga...

Contact: Marsha A., ID: 23933
Dennis Rental
New listing-Bright, sunny home 1.5 miles to Mayflower Beach
3BR
1 ½ bath
Sleeps 8

Off season monthly rental price is $1900/month. This property is available for off-season rentals and is ideal for those seeking a longer stay. We’re ...

Contact: Tracy Coughlan, ID: 24103
East Dennis Rental
E/Dennis 3Br Renovated Getaway, Close to top Beaches!
3BR
1 ½ bath
Sleeps 8

Offering monthly rentals during the off Season for $4500 per month with all utilities included. Inquire today with questions or bookings!

Contact: Matthew, ID: 40613
Dennis Port Rental
Charming Updated Home w/ Central A/C in Heart of Dennisport
3BR
1 bath
Sleeps 6

Available off-season 2026-2027, $2,000 per month, not including gas/electric with monthly availability November 2026 through May 2027 with First and ...

Contact: Rich, ID: 38206
Dennis Port Rental
Prime Cape Location: Golf, Dining, Drama, and Deep Blue Sea
3BR
2 baths
Sleeps 6

Special pricing available upon request $3,500-$4,000/mo negotiable

Contact: Jen, ID: 40898
Dennis Rental
10 minute walk Mayflower/Bayview Beach Clean
2BR
1 bath
Sleeps 5

contact if interested in a summer of extended stay on the Cape Summer - 8500 Sholder season - $6000 Winter - TBD

Contact: Fred, ID: 41952
East Dennis Rental
Bright & Breezy Bayside Condo
2BR
1 bath
Sleeps 4

Available Sept 2026 -May 2027 of fully furnished and well supplied unit for 1900/month including utilities.

Contact: Joanne Masone, ID: 38343
East Dennis Rental
Sesuit Neck Cottage Walk to Beach/Marina/Sesuit Harbor Cafe!
2BR
1 bath
Sleeps 4

Summer 2027 monthly rental is $22,500 per month. Must be 31 days or more to avoid lodging tax.

Contact: Nick, ID: 40747
Dennis Port Rental
Anchors Away Cottage/Bassett Lane
2BR
1 bath
Sleeps 4

Winter rental available October 17th, 2026 - May 15th, 2027. $1,800.00 - $2,000 per month, heat, hot water and electricity included.

Contact: Norman, ID: 39864