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Massachusetts | Cape Cod

Camp Carlton

6 bedrooms·5 bathrooms·16 guests
Views of the water
Lakefront
Pool table
Heated pool

Uncover a hidden gem as you step onto this expansive vacation haven, perfectly designed to accommodate up to 16 wanderlusters. Divided into two distinct dwellings, the property promises a mix of relaxation and recreation. Both the main house and the secluded guest cottage showcase vast decks with ample lounge seating. As the sun sets, gather at the main house deck, and delight in waterfront dining under umbrella-shaded tables. Enhancing the outdoor experience, an enclosed shower and a gas grill await those perfect barbecue evenings. Dive into the interiors of the main house to witness roomy spaces designed for memorable gatherings. A contemporary kitchen boasts top-tier appliances, crowned with a grand island and granite countertops. Adjacent to it, a dining area for ten invites guests to dine with an alluring water backdrop. For leisure, engage in the vast living room with plush sofas, or let the state-of-the-art smart frame TV captivate your senses. The house thoughtfully offers various levels with comfortable bedrooms, a pool table, and even a dedicated workspace for those blending leisure with work. Not to be overlooked, the lower level introduces additional bedrooms and a media room, ensuring everyone finds their cozy corner. Venture towards the back, and the guest cottage greets with serene privacy. A welcoming deck overlooks the tennis/pickleball court, setting the scene for thrilling matches. The cottage interior boasts a functional kitchen, a dining setup for six, and a spacious living area. For fitness enthusiasts, an exclusive third structure filled with workout gear ensures no break in routine. Throughout the property, enjoy seamless connectivity with high-speed Wi-Fi, immersive tunes via the Sonos® sound system, and state-of-the-art cooling with air-conditioned split units. Dive into this captivating oasis and craft memories that last a lifetime.

Our promise

Satisfaction Guarantee

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
Cornhole boards
Outdoor dining
Misc
WiFi
Beach chairs
Beach towels
Boogie boards

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

Private chef

In-home massage

In-home massage

Beach rentals

Beach rentals

Pre-arrival groceries

Pre-arrival groceries

Alcohol delivery

Alcohol delivery

Private driver

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
Bedroom 5 - Main Level: Queen
Bedroom 6 - Main Level: Two Twins
Loft Main House - Second Level: Two Doubles

Location

Inside the destination

Neighborhood: East Orleans - 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

Garage parking available

We're here to help

Whether you have questions on this home or want us to source other options, we're a message away!

Reviews

ILS

It's the nicest house I've ever rented. The owners thought of everything, they covered everything. It ticked every box. They even have a pizza cutter. Such a great place. Perfect for families.

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Quiet Hours: 8:00 PM - 8:00 AM
No smoking allowed
No events allowed
Pets welcome

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

75% Refund: Receive a 75% refund 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

Rents Friday to Friday in Peak Summer.

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

You will be provided with a “starter set” of cleaning/paper products. 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. We ask that you 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

  • No animals, birds, or pets of any kind unless explicitly approved in the lease. Violation fee: $5,000.
  • Smoking or vaping is prohibited anywhere on the premises. Violation fee: $5,000.
  • Illegal activities and fireworks are strictly prohibited.
  • 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 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.
  • 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

  • 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 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.