Guesthouse holiday rentals in Cape Cod Bay

Nautical loft guest house with hot tub and sauna

Keep it simple at this peaceful and centrally-located space. Walking distance to several downtown shops and restaurants, and only one mile from the beach, this loft boasts skylights, cedar hot tub and sauna, outdoor shower and full kitchen. If you are traveling through Sandwich, this loft is a must-see. We recommend this space for two people. While you can technically fit 4, it is quite crowded. If you plan to use the hot tub or sauna, please let us know in advance so we can set it up for you.

Location · Value · Hot tub

Charming Antique Cape Cod Cottage

Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure. Be sure to check out our fall and holiday specials. OCTOBER, NOVEMBER AND DECEMBER - BOOK 3 NIGHTS GET FOURTH NIGHT FREE!

Family · Location · Accuracy

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Family · Value · Condition

Abundant Blessings Cottage – Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

Location · Value · Bathroom

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

Family · Value · Walkability

Madaket Bright and Airy Guest Cottage

Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

Family · Value · Backyard

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Location · Family · Access

“The Pink Cottage” in Historic South Yarmouth

“The Pink Cottage” is a charming one-bedroom private building nestled into a beautiful historic property in South Yarmouth. Enter through the pergola patio, enjoy a spacious living space with dining and kitchen area. The one-bedroom with large closet is comfortably outfitted with all linen necessities, full bath with stand-up shower. Outdoor shower just off the patio, grill and more! Very quiet and private.

Value · Family · Wi-Fi

Bungalow by the Bay

Just a quick walk to Barrington town beach, you’re private space is nestled in a quaint 1920’s bungalow neighborhood. You have a gardened courtyard, access to outdoor shower and gas grill. Bring your bike and enjoy the bike path from Bristol to Providence. Shopping, dinning, all accessible by car, bike or public bus.

Location · Value · Access

Private Harbor Hideaway -walk Scituate to harbor!

Our Harbor Hideaway is located above the detached garage one block from Scituate's beautiful harbor shops, restaurants, and marina! Come enjoy our many beaches and relax in your private backyard! *Mini splits provide heat and A/C. *Cleanliness is a priority and have it professionally cleaned after each guest.

Location · Family · Walkability

Oak bluffs cottage Perfect place to honeymoon!

Cottage in a quiet part of Oak bluffs. 1/2 Mile from beaches, stores and restaurants. Close to bus lines.Our 2026 calendar now open If you’d like to book! We book up early so please Contact us early for your reservation. Fully heated And air conditioned. No BBQ d/t fire risk and insur. Policy.

Location · Family · Beach

Light-filled North Truro cottage-Lovely gardens

Open and airy cottage with lots of attention to detail. Peaceful setting, clean and comfortable. Beautiful view of undeveloped hillside from all three rooms. Quick walk to beach. Set back from the road, nestled amongst gardens for a private feel.

Family · Location · View