See more homes in Massachusetts | Cape Cod

1/59

Massachusetts | Cape Cod

Camp Carlton

Name: Camp Carlton
Brand: KEY.co

6 bedrooms·5 bathrooms·16 guests

Views of the water

Beach access

Pool

Overlooking Little Pleasant Bay, this remarkable 2.4-acre waterfront compound brings together a spacious main house and private guest cottage with accommodations for up to 16 guests. Expansive interiors offer multiple gathering areas, a beautifully equipped kitchen with granite countertops, generous dining spaces with water views, a media room, and a classic pool table. The separate guest cottage adds its own full kitchen, living and dining areas, and private deck, providing additional space and flexibility for larger groups. Outdoor amenities create an exceptional Cape Cod retreat, highlighted by a large heated covered pool, private beach, and access to a tennis and pickleball court shared with just one neighboring property. Kayaks invite leisurely exploration of the bay, while spacious decks provide picturesque settings for outdoor dining and relaxation. A separate fitness space adds another thoughtful amenity, and the restaurants, shops, and entertainment of Orleans and Chatham are just a short drive away.

Our promise

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

KEY Curation Notes

Private beach on Little Pleasant Bay with kayaks provided for on-water exploration. The compound sits on 2.4 acres — formerly the Pleasant Bay Sailing Camp — at the end of a private road.

Heated and covered pool, open Memorial Day through Columbus Day — plus a private tennis/pickleball court shared with just one neighbor. The combination of bay beach, pool, and court on a single property is unusual at this market level.

Regulation pool table in the main house loft, with bay views — a genuinely entertaining secondary space alongside a dedicated media room on the lower level.

Two primary king suites in the main house, a full-kitchen guest cottage at the rear of the property, and a third structure with a gym — giving a group of 16 meaningful separation and independence.

10 minutes to Orleans center, 15 to Chatham — well-positioned for both casual and destination dining without being in the middle of either town.

Sonos sound system and per-room split AC throughout both structures for customized cooling. Linens included, beds made on arrival. KEY.co can arrange grocery delivery before you check in.

Amenities

Indoor

Air conditioning

Dryer

Fireplace

Entertainment room

Internet

Outdoor

Outdoor grill

Heated pool

Pool

Auto-retractable safety pool cover

Corn hole boards

Misc

Beach towels

Carbon monoxide detector

Fire extinguisher

Garage

Generator

Elevate your stay with add-on services

Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.

Private chef

In-home massage

Beach rentals

Pre-arrival groceries

Alcohol delivery

Private driver

Bedroom details

Bedroom 1 - Main Level: King

Bedroom 2 - Second Level: King

Bedroom 3 - Lower Level: Three Twins

Bedroom 4 - Lower Level: Three Twins

Loft Space - Second Level (Main House): Two Doubles

Bedroom 5 - Main Level (Guest Cottage): Queen

Bedroom 6 - Main Level (Guest Cottage): Two Twins

Location

Inside the destination

Neighborhood: East Egg - Just a 10-minute drive to Orleans Center, and 15 to Chatham, both offering destination dining, shopping, and entertainment, including Cape Cod League baseball.

Parking information

During peak hours at town beaches, parking stickers are required. Of course, most of our properties are directly on or within easy walking distance of private, neighborhood association beaches, so no pass is required. For those properties that aren’t right on or within walking distance a pass is necessary. You can stop by the town offices to pick up a weekly pass or pay per visit. Beach passes are issued by vehicle so are not transferable.

Reviews

Katie

The view was incredible and could be enjoyed both from the porch and the dining room table which was great for my parents with limited mobility. The pickle ball court and pool were absolutely amazing and kept the younger set busy. Loved it!

Policies

Check-in: 4:00 PM

Check-out: 10:00 AM

No smoking allowed

No events allowed

No pets

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

Full Refund: Receive a full refund (excluding credit card fees) when you cancel your reservation at least 120 days before check-in.

No Refund: Reservations canceled 119 days or less before check-in are not eligible for a refund.

Refunds subject to a 5% processing fee of the total.

Things you need to know

Self check-in / check-out

This property has a seven-night minimum during the peak season and rents Friday to Friday during peak weeks/summer.

Fresh sheets and bath towel sets for each guest are provided. A bath towel set includes a bath towel, hand towel and face cloth. Bed linens at the premises are provided – no need to pack them and bring them with you.

A “starter set” of cleaning/paper products is also provided. There will be paper towels and bath tissue to start off your week. Similarly, you will be provided with cleaning products like dish soap, laundry detergent, all-purpose cleaners, etc. Please replace what you use so the guests coming in after you can enjoy the same convenience. Some kitchen trash bags will also be provided.

Restrictions

Guests & Occupancy

No more than the number of guests listed on the lease may occupy the property at any time, including infants, children, and overnight visitors.
Guests are responsible for all damage, loss, or added expenses incurred during the stay (including pay-per-view charges). All known damage or loss must be reported before departure to remain eligible for accidental damage coverage.

Events & Noise

Weddings, receptions, reunions, or any gathering exceeding the approved occupancy are prohibited without prior written approval. Failure to obtain approval will result in a penalty equal to an additional full weekly rental rate.

Prohibited Activities

Pets: No animals, birds, or pets of any kind unless explicitly approved in the lease. Violation fee: $5,000.
Smoking/Vaping: Smoking or vaping is prohibited anywhere on the premises. Violation fee: $5,000.
Illegal Substances & Fireworks: Illegal activities and fireworks are strictly prohibited.
Security Cameras: Tampering with, disabling, redirecting, or obscuring exterior security cameras (e.g., Ring doorbell) is prohibited and may result in lease cancellation. No interior cameras are used.

Equipment & Amenities

Utilities are provided (electricity, water, gas if applicable, heat, trash). Guests must use utilities responsibly and avoid waste.
Appliances & Equipment _(if equipped)_: Appliances and equipment (HVAC, internet, cable TV, dishwasher, washer/dryer, gas grill) are maintained but not guaranteed. No refunds will be issued for outages or malfunctions.
Parking: The number of vehicles parked at the property may not exceed the number listed on the lease and must be parked only in assigned spaces. Camper vehicles or vehicles providing sleeping accommodations are not permitted without prior written approval.

Checkout & Care

Check-in: 4:00–6:00 PM (early arrival only if confirmed). Check-out: 10:00 AM. Guests must text upon departure to notify housekeeping. Late Checkout Fees: $500 per hour (or portion thereof) for up to two hours past checkout. After two hours, additional lease penalties apply. The property must be left clean and in good, habitable condition per the checkout checklist. Lost key fee: $25 per key.

Liability & Disclaimers

Not responsible for lost or stolen items. Guests must pay shipping and handling for any items requested to be returned after departure.
Guests assume all risk for injury, loss, or damage resulting from use or misuse of the property or its fixtures and agree to indemnify the landlord and agent.
May enter the property with reasonable notice to inspect, make repairs, or protect the premises.
Minor or non-material changes to furnishings, fixtures, equipment, or property details do not constitute liability.
Failure to comply with lease terms may result in eviction with as little as two hours’ notice and additional charges equal to a full weekly rental rate, plus legal fees if enforcement is required.
Not liable for additional losses if the property becomes unavailable or uninhabitable due to fire, casualty, or legal violation; rent will be prorated or refunded accordingly.