Welcome to Pretty Picky Properties

We specialize in vacation rentals only, and only premier homes and cottages on the Lower Cape, mostly on or very near the beach. Please click on any of the photos below to see more photos of each of these Pretty Picky Properties. Then click on the "Contact" link at the left to reach us with any questions. We're eager to help you experience the Cape Cod summer vacation of your life!

NOTE: Rates and availability subject to owner confirmation.

Sleeps up to 12

Check Property Availabilities!

Property ID: 083-B

BREWSTER

Rare beach front home with plenty of living space

Please ask about June & September rates

Sleeps: 12

Bedrooms: 4

Baths: 2 full baths plus shower/dressing room

Wireless Internet

Property ID: 076-B

BREWSTER

Vacation togetherness & privacy in one big

Bayside home

In-Season: $5,800

Off-Season: Please ask

Sleeps: 12

Bedrooms: 6

Baths: 4 full plus outdoor shower

Central air conditioning

Wireless Internet

Property ID: 270-B

BREWSTER

Living space to spare in big family home by beach

In-Season: $5,200

Off-Season: Please ask.

Sleeps:12

Central air conditioning

Property ID: 061-B

BREWSTER

Superb new custom built home by the Bay

In-season: $6,200

Off-season: Please ask

Sleeps: 10

Bedrooms: 4 plus queen convertible

Baths: 3 full plus outdoor shower

Central air conditioning

Property ID: 055-E

EASTHAM

Spacious Eastham house, three-minute walk to perfect, private beach

In-season: $5,300

Off-season: Pease ask

Sleeps: 10

Bedrooms: 5

Baths: 3 full plus outdoor shower

Property ID: 040-B

BREWSTER

Captivating property on Brewster beach

offers main cottage plus separate "4th

of July" house.

In-season: $5,500

Off-season: $4,500

Sleeps 10-11

Bedrooms: 6

Baths: 2 1/2 baths plus outdoor shower

Property ID: 590-O

ORLEANS

Exquisite Orleans summer home across the road from Pleasant Bay

beach

In-season: $4,800

Off-Season: Please ask.

Sleeps: 10

Air conditioning, wireless Internet

Property ID: 014-B

BREWSTER

Spacious new custom built home by the beach

In-season: $4,800

Off-season: Please ask

Sleeps: 10

Bedrooms: 4 plus extra room

Baths: 3 1/2

Central a.c., wireless Internet

Property ID: 037-O

EAST ORLEANS

Beachfront cottage, sweeping views of Nauset Beach

In-season: $5,000

Off-season: Please ask

Sleeps: 10

Bedrooms: 5

Baths: 2 full baths plus outdoor shower

Cable TV, high-speed Internet

Property ID: 012-B

BREWSTER

Sweeping Beach & Bay Views, Upscale Amenities Right on the Beach!

In-season: $6,500

Off-season: Please ask

Sleeps: 10

Bedrooms: 5

Baths: 2 plus outdoor shower

Washer/dryer, spare fridge,

multiple flat screen TVs, wi-fi

Property ID: 045-B

BREWSTER

Striking New Custom Built Home on the Beach

In-season: $6,500

Off-season: Please ask

Sleeps: 8-10

Bedrooms: 4

Baths: 3 1/2 plus outdoor shower

Property ID: 633-O

NORTH CHATHAM

Classic Renovated Sea Captain's Home Provides

the Perfect North Chatham Escape

In-season: $2,700

Off-season: Please ask

Sleeps 8-10

Bedrooms: 4

Baths: 2 1/2

Property ID: 047-B

BREWSTER

Roomy, bright vacation home sleeps 10, 4 minutes walk to beach.

In-season: $4,500

Off-season: Please ask

Sleeps 8-10

Bedrooms: 4

Baths: Three full, outdoor shower, hot tub

Wireless Internet, AC window units

Property ID: 046-O

EAST ORLEANS

5BR restored, tony Nauset Heights cottage overlooks the Atlantic.

In-season: $6,200

Off-season: $4,300

Sleeps 10-11

Bedrooms: 5

Baths: 2 1/2 plus outdoor shower

Central AC, wireless Internet

Page: 59 Locust

Property ID: 059-WB

WEST BARNSTABLE

Stunning architect-owned home with pool and sweeping views

of Sandy Neck

In-season: $4,200

Off-season: Please ask

Sleeps: 10

Bedrooms: 4

Bathrooms: 3 full

In-ground pool

Central air conditioning

Property ID: 045-E

EASTHAM

Large, premier quality Eastham home on private beach

In-season: $7,500

Off-season: Please ask

Sleeps 8

Bedrooms: 4

Baths: 3 full, 1 half bath

Property ID: 018-B

BREWSTER

Bayside gem with limited weeks,

unlimited quality.

In-season: $5000 - $7,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 Baths: 3 1/2

Property ID: 067-B

BREWSTER

Directly on the beach, with sweeping

Bay views from virtually every window!

In-season: $5,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Property ID: 117-B

BREWSTER

The beachfront vacation you've always

imagined.

In-season: $4,900

Off-season: Please ask

Sleeps: 8

Bedrooms: 5

Baths: 2 full plus outdoor shower

Property ID: 015-B

BREWSTER

Immaculate beach house just steps from

Cape Cod Bay

In-season: $4,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Wireless Internet, washer & dryer

Property ID: 090-B

BREWSTER

Sweeping Bay views from two-story cottage

directly on the beach.

In-season: $3,800

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 Baths: 1

Stackable washer/dryer

Property ID: 115-B

BREWSTER

Charm and privacy right on the beach

In-season: $4,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 1 full bath plus outdoor shower

Cottage-wide deck plus screened porch

Internet, Cable TV

Property ID: 222-B

BREWSTER

Pristine family cottage commands Bay

view

In-season: $4,400

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Property ID: 008-O

EAST ORLEANS

Idyllic vacation home just over the dunes from

secluded section of Nauset Beach.

In-season: $3,500

Off-season: $2,200

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Wireless Internet

Property ID: 068-B

BREWSTER

Roomy cottage directly on Cape Cod

Bay. Air conditioning.

In-Season: $3,500

Off-Season: Please ask

Sleeps: 8

Bedrooms: 4, air conditioning

Baths: 1 full plus outdoor shower

Property ID: 260-E

EASTHAM

Cheery Vacation Home, Under 4-Minute Walk To Stunning Eastham Beach

In-season: $4,400

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Some window air conditioners

Wireless Internet

Baths: 2 1/2 plus outdoor shower

Property ID: 105-B

BREWSTER

Light, bright vacation home on the Bay,

architect owned and renovated

In-season: $5,200

Off-season: Please ask

Sleeps: 8

Bedrooms: 3

Baths: 1 1/2 plus outdoor shower

Property ID: 030-O

EAST ORLEANS

Classic family summer beach house,

breathtaking views of Nauset Beach

and the Atlantic Ocean

In-season: $4,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 6

Baths: 2 full plus outdoor shower

Property ID: 280-B

BREWSTER

Immaculate beach front house overlooking Cape Cod Bay

In-season: $5,200

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 1/2 plus outdoor shower

Property ID: 116-B

BREWSTER

Family vacation home directly on Cape Cod Bay

offers stunning view and very private yard

In-Season: $5,500

Off-Season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 3 full plus outdoor shower

Wireless Internet

Window air conditioners

Property ID 101-B

BREWSTER

Pond view and access, walk to Bay beach

In-season: $4,200

Off-season: Please ask

Sleeps 8

Bedrooms: 3

Baths: 3 full plus outdoor shower

Central air conditioning

Wireless Internet

Property ID 375-C

CHATHAM

Large, pristine Chatham home, private

tennis court. Walk to beach, Town.

In-season: $8,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 5

Baths: 4 full

Air conditioning

Wireless Internet

Property ID 049-O

EAST ORLEANS

First time rental. As close as you can

get to Nauset Beach.

In-season: $5,000

Off-season: Please ask

Sleeps: 8-9

Bedrooms: 4

Baths: 2 full plus outdoor shower

Central air conditioning

Cable TV, wireless Internet

Property ID 013-O

ORLEANS

Pristine, secluded custom built home

includes heated pool.

In-season: $4,200

Off-season: Please ask

Sleeps 8

Bedrooms: 3

Baths: 3 1/2 plus outdoor shower

Central air conditioning

Cable TV, wireless Internet

Elevator from garage to main level

Property ID: 071-B

BREWSTER

Impeccably kept vacation beach house,

200 feet from the beach

In-season: $4,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 plus Family Room convertible

Baths: 2 full, 1 half bath, outdoor shower

Central air conditioning, wireless Internet, Cable TV

Property ID: 036-C

NORTH CHATHAM

Newly updated, secluded home in North Chatham

In-season: $2,500

Off-season: Please dask

Sleeps: 8

Bedrooms: 3

Bathrooms: 3 full plus outdoor enclosed shower

Central air conditioning

Property 015-E

EASTHAM

Pristine Eastham Bayside Home with Separate In-Law Apartment

In-season: $2,500 - $3,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 plus In-Law Apartment

Baths: 3 full, outdoor shower

Property ID: 078-B

BREWSTER

Classic Cape Beach Cottage on Cape Cod Bay

In-Season: $3,600

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full plus outdoor shower

Property ID: 074-B

BREWSTER

Cozy cottage on private Bayside beach

In-Season: $3,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full plus outdoor shower

Property ID: 089-B

BREWSTER

Spacious beach house nestled in dunes,

100 feet to private sandy beach

In-season: $2,900

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 1/2 plus outdoor shower

Property ID: 054-D

EAST DENNIS

Commanding Bay views & 100+ yards to sandy Dennis beach

In-season: $3,000

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full, 1 half bath

Property ID 260-B

BREWSTER

House on Beach with Extras

In-Season: $4,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 2 full plus outdoor shower

Window AC units throughout

Property ID: 326-C

CHATHAM

Impeccable Chatham vacation home

on Morris Island Road

In-Season: $5,200

Off-Season: Please ask

Sleeps 6

3 Bedrooms

3 Full baths, half bath plus outdoor shower

Property ID: 125-B

BREWSTER

Large, exquisite cottage, 300 feet from

perfect sandy beach on the Bay

In-Season: $4,200

Off-Season: Please ask

Sleeps: 6

Bedrooms: 4

Baths: 2 1/2 plus outdoor shower

Property ID: 063-B

BREWSTER

Spotless Brewster beach house with Bay views

In-Season: $4,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 3 full baths

Property ID: 051-O

ORLEANS

Spectacular water views of Nauset Beach from classic Cape cottage

In-season: $4,900

Off-season: Please ask

Sleeps: 6-7

Bedrooms: 3

Baths: 3 Full Baths, plus outdoor shower

Property ID: 239-C

CHATHAM

Classic Sea Captain’s home located in the heart of Chatham Village.

In-season: $3900 - $4500
Off-season: $ 3100 - $3500
Sleeps: 10
Bedrooms: 5
Bathrooms: 3 full

Property ID: 259-B

BREWSTER

Just renovated beach house on Cape Cod Bay

In-season: $4,500

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full plus outdoor shower

Cable TV, wireless Internet

Property ID 043-O

ORLEANS

Casual cottage elegance, directly

on Nauset Beach

In-season: $3,800 - $4,600

Off-season: $3,200

Sleeps: 6

Bedrooms: 2

Baths: 3 full plus two outdoor showers

Central air conditioning (new cottage)

Cable TV, wireless Internet

Property ID: 588-O

ORLEANS

Beautifully renovated home, across the

road from sandy Pleasant Bay beach.

In-Season: $3,800

Off-Season: Please ask

Sleeps 6

3 Bedrooms

2 1/2 baths plus outdoor shower

Property 071-O

ORLEANS

Secluded waterfront property between Skaket and Rock Harbor

In-season: $3,200 - $3,800

Off-season: Please ask

Sleeps: 8

Bedrooms: 4 plus 2 daybeds

Baths: 2 full plus outdoor shower

Property ID: 015-D

DENNIS

Views of the Bay and just steps from Mayflower Beach

In-season: $2,850

Off-season: $2,100

Sleeps: 6

Bedrooms: 3

Baths: 1 full, 2 half plus outdoor shower

Property 069-B

BREWSTER

Beach house with latest amenities, 200 feet from Bay beach

In-season: $$3,800 - $4,100

Off-season: Please ask

Sleeps: 8

Bedrooms: 3

Baths: 2 1/2 plus outdoor shower

Quick Links:

Sleeps up to 10

Sleeps up to 8

Sleeps up to 6

NEW! Pretty Picky Linen Service

Clean, fresh linens waiting at your property when you arrive. Click here for more information.

Property ID: 061-O

ORLEANS

Secluded cottage charm, four minutes to private Bay beach

In-season: $1,900

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full, outdoor shower

Property ID: 108-B

BREWSTER

Commanding Bay views from beach front two-story cottage

In-season: $4,200

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 2 full plus outdoor shower

Property 065-O

ORLEANS

Superb upscale home with acres of privacy directly on the Bay.

In-season: $6,785

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 3 1/2 plus outdoor shower

Central air conditioning

Wireless Internet

Property ID: 029-O

ORLEANS

Expansive views of Nauset Beach from this spacious beach-side home

n-Season:$4,950-5,200/week
Off-Season: $3,700
Sleeps: 8
Bedrooms: 5
Baths: 3 full 1 half bath

Property ID: 077-C

CHATHAM

In-Season: $4,000

Off-Season: Please ask

Sleeps: 6

Bedrooms: 4

Baths: Two full, two half -baths, outdoor shower

Custom kitchen, washer/dryer,
window air conditioners