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Long-Term Vacation Rentals in Wellfleet

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: 35

Wellfleet

Waterfront Cape Cod Cottage with private beach 5 bedrooms
5BR
2 ½ baths
Sleeps 16

September and October weeks available 50% off($5000)

Contact: Robert Cutting, Property ID: 18627

Steps to Private Beach. Big Beach house. 5 Kayaks.
5BR
2 baths
Sleeps 11

December, January, February. $2,400/mo

Contact: Howard Feinstein, Property ID: 14678

Gorgeous newly renovated house, steps to downtown Wellfleet
5BR
3 ½ baths
Sleeps 10

Also available upon request and rates vary from 1,500 to 2,000 per month.

Contact: Fernanda, Property ID: 20707

Contemporary with Open Floor Plan 2 Blocks from Mayo Beach
5BR
3 ½ baths
Sleeps 10

Off Season September 30 to July 1 $5,500 a week.

Contact: Eve Lorenz, Property ID: 27256

Wellfleet Spacious Contemporary, Walk to Town & Bay Beaches
4BR
2 ½ baths
Sleeps 10

This home is available for a long-term winter rental November through March/April. Price negotiable.

Contact: Jessie , Property ID: 13026

A Charming Bayside Cottage With A Great Yard
4BR
2 baths
Sleeps 10

Hidden Hollow Cottage is available for month-long rentals from September to May. Please check the calendar for specific rates and availability. If i...

Contact: Tom or Angela Keer, Property ID: 16004

Impeccable 4BR Bayside Cottage
4BR
2 baths
Sleeps 10

If you are looking for a long term winter rental please call Sarah directly at 617-230-1413 to discuss pricing and availability.

Contact: Sarah, Property ID: 8717

Wellfleet Modern 3Br, Hot Tub, Game Room, Dog Ok, Near Ocean
3BR
2 baths
Sleeps 10

October through April with price based on occupancy. The house is heated and until recently occupied year round. The separate Game Room building has r...

Contact: Matt & Marie, Property ID: 31917

Spectacular home on Gull Pond. Short walk to beach
5BR
3 baths
Sleeps 8

Available upon request

Contact: Anne, Property ID: 33825

Bound Brook Island Paradise. Modernized Antique Cape.
4BR
2 ½ baths
Sleeps 8

n/a

Contact: Jared, Property ID: 31974

Chequessett Bluff Road, 4 BR w/AC, 200 yards to Mayo Beach
4BR
2 baths
Sleeps 8

.8 of a mile (3 minute drive) to Chequessett Yacht & Country Club for golf, tennis and sailing. .5 mile to public tennis courts, basketball court and ...

Contact: Richard, Property ID: 32933

Paine Hollow Pleasure: Water Views & Walk to Beach
4BR
2 baths
Sleeps 8

The house is fully winterized and has a wood burning stove in the living room. Off-season and long-term rentals are possible. $3500 - $2000 month. p...

Contact: Alison Landes, Property ID: 24751

Create memories here! Private, close to everything, TREES!
4BR
2 baths
Sleeps 8

No long term winter rental.

Contact: Rebecca Hansen, Property ID: 25891

Stunning Water Views from ''Windward'' on the Bay
4BR
2 ½ baths
Sleeps 8

Windward has been rented by artists and writers for up to 6 months. The fee is much dependent on number of people at the house and how the house is pl...

Contact: Windswept, Property ID: 3600

Waterfront.Walls of glass.Views surround.Walk to town.A/C
4BR
2 baths
Sleeps 8

Considered upon request.$6,000-$8,000. Non-refundable deposit required to secure rental, fully refundable damage deposit also required.

Contact: Kathy, Property ID: 5527

Winterwood - Walk to Dyer Pond and village
4BR
2 ½ baths
Sleeps 8

Monthly rates available - October 2020 ($4,500). Will consider 2020-2021 monthly off-season rentals. Please inquire.

Contact: Heidi Ganss Harris, Property ID: 23931

Not Your Average Beach House--Walk to Gull Pond
4BR
3 ½ baths
Sleeps 8

Our home combines the charm of a beach cottage with year round, cozy livability. Available off season mid-October through mid-June. Monthly rate $14...

Contact: Susan Robinson, Property ID: 11051

Secluded Gem in Village: 2021 Calendar now posted
3BR
2 baths
Sleeps 8

Monthly rental is available from Sept - May; see rates on the Pricing Calendar. Utilities are included except for trash collection (which is available...

Contact: Bob and Fran, Property ID: 8592

Charming Seaside Cottage in National Seashore
3BR
1 ½ bath
Sleeps 8

April and May, and also September and October are available for full time rental, at $1000/wk, 3000/mo

Contact: Pamela Blau, Property ID: 9299

Newly Renovated; 2.5 miles from Cahoon Hollow Beach
3BR
3 baths
Sleeps 8

Note: WiFi is on during July and August. If we know in advance that you would like WiFi off-season, let us know and we may be able to arrange it. Othe...

Contact: Deborah & Jeffrey Roth-Howe, Property ID: 22224

Wellfleet Gem – Close to Beaches and Town, Central A/C
3BR
2 baths
Sleeps 8

September and October monthly rentals available for $6000. Please contact for more details.

Contact: Sheldon, Property ID: 29425

Highland House-Pleasant Point: Peaceful Home w/Central AC
3BR
2 baths
Sleeps 8

The house is available off season. Monthly rate for offseason is $3000/month.

Contact: Ricki, Property ID: 31578

3 BR Cottage Near National Seashore and Rail Trail
3BR
3 baths
Sleeps 8

Nov-April, $3,300/month utilities included

Contact: Bill & Joy O'Connor, Property ID: 32564

Special Modern Home
2BR
1 ½ bath
Sleeps 8

Long-terms rentals welcome November-March; $2600 per month including garbage and recycling, cable, wifi, heat and electricity.

Contact: Susan and Clint, Property ID: 25150

Amazing and Convenient in the Heart of Wellfleet
4BR
1 bath
Sleeps 7

Home is Available for Long Term Rentals Starting at $1550/month Six Month Lease Required

Contact: Allen Dalby, Property ID: 13155

Beachside Home at LeCount Hollow Beach with A/C
3BR
2 baths
Sleeps 7

Two excellent golf courses nearby (Chequessett in Wellfleet and Highland in Truro).

Contact: John Regan, Property ID: 21479

Waterfront Beauty on Chipman's Cove - Steps from the Water
3BR
1 bath
Sleeps 7

Longer, off-season stays a possibility. Inquire w/owner. Perfect setting for writers/artists. One month minimum. November thru May only.

Contact: William P. Nicholson, Property ID: 2339

Spacious, Bright, & Clean w/ Screened Deck
3BR
2 baths
Sleeps 6

Off-Season - Long and Short term rentals are available.

Contact: Ted or Vanessa, Property ID: 34173

On gorgeous private beach, two kayaks
2BR
1 ½ bath
Sleeps 6

We regret that we are not able to accommodate long term rentals.

Contact: Sarah, Property ID: 15835

Indian Neck area - short walk to beach - private location
3BR
1 bath
Sleeps 5

Discounted monthly rate of $2,750 for September & October, 2018. Available starting Sept 2.

Contact: Heidi Ganss Harris, Property ID: 10233

2 BR Brick Cottage w heat & AC Steps from Mayo Beach
2BR
1 bath
Sleeps 4

This property is perfect for the academic or the artist in need of a peaceful, warm and cozy, getaway to complete academic work or artistic endeavors....

Contact: Rosemary, Property ID: 31649

2 BR Brick Bungalow - 35 Steps from Mayo Beach
2BR
1 bath
Sleeps 4

This property is perfect for the academic or the artist in need of a peaceful, warm and cozy getaway to complete academic work or artistic and Deavors...

Contact: Rosemary, Property ID: 31695

Sweet Serenity: Newly renovated, Next to Conservation Land
1BR
1 bath
Sleeps 4

Month-to-month rentals during off season. Please check with Owner. Monthly rates are $1400.

Contact: Lisa and Denise, Property ID: 34140

Private Apartment in Historic Home near Wellfleet Library
2BR
1 bath
Sleeps 2

Ask about availability and pricing.

Contact: Gail, Property ID: 10392

Charming Cottage Overlooking Wellfleet Harbor
2BR
1 bath
Sleeps 2

Sleeps 2 in 2 bedrooms. Discount is available for rentals longer than 1 month. $1,400 - 2,250 per week dependent upon season.

Contact: Joanne, Property ID: 17736