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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: 26

Dennis
Dennis Rental
Private and Magical Family Compound, Private Pool, Sleeps 15
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
Dennis Rental
Now renting through HomeLand Realty in Dennis 508-385-1331
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, ID: 26759
East Dennis Rental
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 , ID: 11848
East Dennis Rental
Walk to Corporation Beach; A/C; Close to Golf, Shops, Dining
4BR
2 baths
Sleeps 12

Long term rental is available for off-season. September 2024 thru June 2025. Price range ($2,300 monthly; long term rate available)

Contact: Moe, ID: 39497
East Dennis Rental
Quivet Neck Beauty - Walk to Sea Street/Cold Storage Beach
4BR
3 baths
Sleeps 10

$3500/month in off season, from roughly October-April

Contact: Billy Hartmann, ID: 38985
Dennisport Rental
Cape Charm with Spacious Yard, side patio and new firepit
4BR
1 ½ bath
Sleeps 10

Yes! In-Season $20,000/month Off Season - Negotiable

Contact: Colleen, ID: 36390
Dennis Village, North of 6A Rental
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, ID: 29759
East Dennis Rental
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, ID: 23036
Dennis Rental
Charming Cape Cottage w/central air, 4 bedrm, porch, patio
4BR
2 ½ baths
Sleeps 8

Available 10/1/2025: $2500/mo, including internet and trash service. The tenant is responsible for gas and electricity. I prefer a total 8-month winte...

Contact: Marsha A., ID: 23933
West Dennis Rental
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 , ID: 32390
West Dennis Rental
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, ID: 34493
Dennis Village Rental
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, ID: 29177
Dennis Rental
3 Bedroom, 2 Full Baths, Sleeps 8, Wifi, Ac.
3BR
2 baths
Sleeps 8

We have Summer Monthly rentals: Take 4-5 weeks During summer season Consecutive weeks at least 33 days: cost is cost is $8500- August weeks through l...

Contact: Maryalice, ID: 20477
Dennis, Scargo Lake Rental
18th Century Cape Cod House w/its own Beach on Scargo Lake
3BR
2 baths
Sleeps 8

$2,500 a month

Contact: Verity Bostick, ID: 9530
Dennis, North Side Rental
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, ID: 10266
Dennis Rental
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, ID: 38663
Dennis Port Rental
Bright & Updated Cottage
3BR
1 bath
Sleeps 7

Available Sept - May $3000/mo, contact for long term inquires and pricing

Contact: SusanneF, ID: 36496
East Dennis Rental
Secluded Family/Pet Friendly Home in E. Dennis, Near Beaches
3BR
2 baths
Sleeps 7

Available October through April as a monthly rental. $4,900 per month, includes all heat and utilities (electric, gas, internet, water).

Contact: Ron, ID: 37939
Dennis Port Rental
Charming Updated Home w/ Central A/C in Heart of Dennisport
3BR
1 bath
Sleeps 6

Available off-season 2024-2025, $1,900 per month, including utilities (gas/electric) with monthly availability Now through mid-June 2025 with a Securi...

Contact: Rich, ID: 38206
Dennisport Rental
3 Bedroom Ranch - Dennisport - Newly Renovated
3BR
1 bath
Sleeps 6

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

Contact: Julie, ID: 28120
Dennis Rental
3BR Ranch. Close to Popular Dennis Beaches with Central Air!
3BR
1 bath
Sleeps 6

$1900 plus utilities September-May or June

Contact: Sheila , ID: 32694
West Dennis Rental
Cape Cod Waterfront Gem w/AC, Boating from Back Yard to Sea
3BR
3 baths
Sleeps 6

Offered as 1 or 2 bedroom winter home from Nov - April for discount rate. Open 1 to 2 bedrooms for up to 2 occupancy. Rate from $1400 for Jan -Marc...

Contact: Nina, ID: 33495
Dennis Rental
Sandcastle by the Sea
2BR
1 ½ bath
Sleeps 6

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

Contact: John, ID: 36007
East Dennis Rental
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, ID: 38343
Dennis Port Rental
Anchors Away Cottage/Bassett Lane
2BR
1 bath
Sleeps 4

Available October thru May. $1,000 - $2,000 per month

Contact: Norman, ID: 39864