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Long-Term Vacation Rentals in Dennis

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: 23

Dennis
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, Property ID: 18302
Beautiful Quiet Private East Dennis Home for Rent Sleeps 12
5BR
3 ½ baths
Sleeps 12

Available for monthly rentals from mid-september until thanksgiving week. And from mid-february until mid-may. Price range from $9000 to $12000

Contact: Jonathan , Property ID: 11848
Great Home and Location for 2 Families(Sleeps 12)
5BR
2 ½ baths
Sleeps 12

Winter rentals are considered. Price $3,500 per month including utilities. Please contact for further information. Thank you!

Contact: Allen & Tania, Property ID: 26759
Central Air/New kitchen/baths 4Bed/2.5Ba North of 6A
4BR
2 ½ baths
Sleeps 10

October through April or May. $3200-$6000/mo

Contact: Caitlin, Property ID: 29759
Perfect Cape Escape - Lovely 4 Bedroom Cape in East Dennis
4BR
2 baths
Sleeps 9

Available for winter rental December - mid-May, $1200 per month plus utilities.

Contact: Jeanine, Property ID: 23036
Walk to Beach Cape House with 4 Bedrooms/2 Baths and AC
4BR
2 baths
Sleeps 8

Long-term winter rentals available upon request. Please reach out for more information as pricing ranges from $2300 to $2500 per month in December, Ja...

Contact: Laura , Property ID: 32390
Swan River Retreat - 5 minute walk to the beach!
4BR
2 baths
Sleeps 8

Off-season winter rental available. $2500/mo plus utilities.

Contact: Geri, Property ID: 34493
Olivia Walker Way Cape Escape
3BR
2 baths
Sleeps 8

Available to rent for January, February, and March $2500 a month excluding utilities, Additional $2500 security deposit required

Contact: Michelle, Property ID: 35527
3 Bedroom, 2 Full Baths, Sleeps 8, Wifi, Ac.
3BR
2 baths
Sleeps 8

Winter rental, Oct - May,Utilities Not Included, 3 bedroom, 2 full Baths, Fully furnished, 1st floor laundry, Open spacious floor plan. Hardwood f...

Contact: Maryalice, Property ID: 20477
100 yards from Bayview Beaches on the North Side
3BR
2 baths
Sleeps 8

Sleeps 6 in 3 BR, 10/1 - 5/15, $2,000. per month plus utilities. Close to beach, golf and shopping. Great getaway house. 1 month security required.

Contact: Tony, Property ID: 10266
Mayflower Beach and Dennis Village
3BR
2 baths
Sleeps 8

Prices start at $3,800 per month. Winter rentals between late fall and early spring are available under a 1 or 2 bedroom modified floor plan configura...

Contact: James, Property ID: 29177
2 miles from Mayflower Beach - Olivia’s Cottage
3BR
2 baths
Sleeps 8

Fully Furnished. Utilities Included. Available November to April. $5000 per month

Contact: Robin, Property ID: 38663
Charming Updated Home w/ Central A/C in Heart of Dennisport
3BR
1 bath
Sleeps 6

Available off-season, $2,000/month, including utilities. Currently rented through June 2024, with monthly availability beginning in November 2024.

Contact: Rich, Property ID: 38206
A Cape Cod Retreat on Scargo Hill - Friday to Friday rental
3BR
2 ½ baths
Sleeps 6

This fully furnished house is available for long term off season rental. It is available October 15 - April 30th for 6000.00 monthly.Housekeeping serv...

Contact: Margaret & Fred Christen, Property ID: 5011
Get a “Wave From it All” at this charming W Dennis 3 bdr
3BR
1 bath
Sleeps 6

We are offering winter rental January - March for $1800 which includes utlities.

Contact: Linda , Property ID: 34337
3 Bedroom Ranch - Dennisport - Newly Renovated
3BR
1 bath
Sleeps 6

October through May - $1,750 a month - Utilities Included

Contact: Julie, Property ID: 28120
Sandcastle by the Sea
2BR
1 ½ bath
Sleeps 6

Long term rentals for October, November, December Weekly $3,750.00

Contact: John, Property ID: 36007
18th Century Cape Cod Cottage with Beach on Scargo Lake
2BR
1 bath
Sleeps 6

$1,200 a month until April 30. Utilities are extra.

Contact: Verity Bostick, Property ID: 19306
Large Saltwater Pool,2 Bdrm Condo 3 Blocks from Inman Beach
2BR
2 baths
Sleeps 5

Long term rental available for September. $750/week or $2200/month

Contact: Sandi, Property ID: 23828
Bright & Breezy Bayside Condo
2BR
1 bath
Sleeps 4

available Sept-May of fully furnished and well supplied unit for 1500/month plus utilities (heat, electricity and wifi).

Contact: Joanne Masone, Property ID: 38343
Walk to the Beach, Restaurants, Ice Cream and More
2BR
1 bath
Sleeps 4

AVAIL 9/15-6/15 $1800/mo including utils if rent for at least 8 months (preferred; up to 2 people). $1950/mo for less time. Ask me!

Contact: Denise, Property ID: 37217
Romantic Getaway * Walk to Beach, Restaurants & Ice Cream
1BR
1 bath
Sleeps 2

1-2 people. Small dog considered (no cats). Avail 10/15/24-5/15/25. $1650/mo for 6+ months (preferred). $1800/mo for less time. 1/2 mile to beach! Que...

Contact: Denise, Property ID: 38125
Neat As Pin East Dennis Efficiency Condo
1BR
1 bath
Sleeps 2

Looking for a long vacation (maybe mixed with some remote work) ... Rent 5 weeks in-season for $4125! Right now you can choose your weeks but that wil...

Contact: Steele Associates, Property ID: 36781