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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: 15

Dennis
Dennis Rental
Private Compound, Private Pool, Dennis Village, sleeps 12+
8BR
8 ½ baths
Sleeps 15

Please inquire for July and August monthly rentals! For either month $75,000.

Contact: Sally, ID: 39972
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
West Dennis Rental
Lazy Swan River Escape
4BR
2 baths
Sleeps 12

Upon request 10k per month

Contact: Allison, ID: 41324
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
Your Perfect Family Vacation Home!
4BR
1 ½ bath
Sleeps 8

Oct 2026 - May 2027. 4 Bedroom furnished home $2500/ mo. Less than 7 months negotiable. I pay for internet & trash. You would be responsible for gas ...

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
South Dennis Rental
East Dennis Bayside Gem
3BR
2 baths
Sleeps 7

Home is available for long-term off-season rental - September through May - please inquire.

Contact: Mariellen , ID: 22675
Dennisport Rental
Beautiful Getaway Close to Beaches, Restaurants
3BR
1 ½ bath
Sleeps 7

Long term winter rental. Available October 1st - April 1st $3000.00 per month includes all but trash and snow plowing

Contact: Martha, ID: 39173
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 October 2026 through May 2027 with First and L...

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 Port Rental
Modern 2 Bedroom Beach Cottage 100 yds to Beach
2BR
1 bath
Sleeps 5

Monthly rentals may be offered in the fall/winter 2025-2026 $2,500-$6,000/mo

Contact: Nancy, ID: 36167
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