Bailey Island Rentals USA Maine Bailey Island

Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. | House in Harpswell

9.8 (58 Reviews) |   2 Bedrooms  2 Bathrooms  6 Guests  Stay&Play
Bailey Island House | Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views.

2 Bedroom House in Bailey Island, Harpswell

Located near the south end of Bailey Island, this comfortable custom-built year-round home sits along the coast with a western view of Casco Bay and the mouth of Mackerel Cove. You can enjoy spectacular sunsets from the house or down on the pier, where you may also see Mt. Washington on the horizon.
The home has two bedrooms. Upstairs, the master loft bedroom has a queen bed and ensuite bathroom with shower. The master loft bedroom also features a western facing private balcony to enjoy your morning coffee or an evening breeze with a glass of wine. The second bedroom, located on the main floor, has a queen size bed. A bathroom is located on the first floor featuring a deep tub and shower.
Providing a private room for additional 1 or 2 guests, there is a den with a double-sized sofa bed. The den also features a desk for remote work access (via wifi) with a beautiful view.
The home is open and airy, but does have air conditioning, if needed. The kitchen has all the utensils needed for cooking that lobster dinner and enjoying the quiet of Bailey Island. The living room features a propane fireplace to remove the chill on early mornings or rainy afternoons. From the living room enjoy stepping out onto the deck for relaxing, reading, or watching lobsterman haul their traps.
We recommend a car for your stay here in Harpswell, Rudman’s Retreat is located 25 minutes from major grocery stores and the town of Brunswick. We hope you will be able to enjoy exploring all the Maine coast has to offer. If you will be flying to Maine, we recommend Portland International Jetport (PWM). If assistance is needed for varying flight arrivals of your party, Safe Harbour Property Management offers concierge rides to and from PWM starting at $125.00.
Please note there is an automatic generator located at this property.
Kayak rental and rate inquiries may be found at:
Seaspray Kayaking 207-404-1100
RIngs Marine Service 207-865-6143

Rudman's Retreat Deep waterfront 2 Bedroom home with spectacular sunset views is located in Bailey Island. Rudman's Retreat Deep waterfront 2 Bedroom home with spectacular sunset views provides accommodation, featuring Sports/Activities, Child Friendly, Air Conditioner, among other amenities. This House features Sports/Activities, Child Friendly, Air Conditioner, to make your stay a comfortable one.

Rudman's Retreat Deep waterfront 2 Bedroom home with spectacular sunset views has 2 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Bailey Island has interesting places to visit. If you want to learn more about the House in Bailey Island, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 22
Check-out Check-out before 10:00 am contactless check-out available
Child Policy Children are welcome.
Pet Policy Note from host: owner allows no exceptions due to health reasons pets not allowed
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Harpswell, 04003, USA

What Our Guests say 500 + Reviews

May 1, 2025 02:07:15 AM
Summary: Overall, great property. Disappointed gas stove was not functional.
Bradford H. Bradford H.
Jan 20, 2025 03:51:52 AM
Summary: We had a great time observing the locals.Those that aren't catching lobsters are serving them in their local restaurants.
Eric M. Eric M.
Sep 4, 2024 03:31:45 AM
Summary: We enjoyed our stay! The property had a great view of the sunset.
Sarah C. Sarah C.
Aug 5, 2024 07:08:17 AM
Summary: I may have left behind (or didn't pack) a couple of men's linen shirts. We are still in the area Aug 3-10 so if you have them, we can arrange to pick them up. overall, we really enjoyed the property. either I didn't notice or it wasn't clear that the 2nd bedroom was in a loft with no ability to close it off. maybe that was my fault. otherwise, I really liked it. very very much. Mike 248-231-1093
michael u. michael u.
Aug 1, 2024 03:19:01 AM
Summary: There isn't much we can say other than what other reviewers have posted. We loved this property unabashedly and are hoping to return next summer (if not sooner!).
David S. David S.
Jun 2, 2024 09:26:17 PM
Summary: We loved our stay on Bailey Island! The views were spectacular! Having coffee by the water in the more was so peaceful. We will definitely go back!
Jennifer B. Jennifer B.
May 26, 2024 10:23:42 PM
Summary: Rudman's retreat isn't a basic cottage on a postage size lot, it is a beautiful, meticulously maintained, 4 season home VERY tastefully decorated with cherry furniture. The waterfront views of lobster boats coming and going was spectacular. Nearby we walked through the woods to an old WW II ocean observation tower and gun emplacements. David, the caretaker was super friendly, responsive, and easy to work with. As NH residents, we were impressed that our former US Senator's family owns this property, even displaying several items from his time as Senator. We will likely return, if they'll have us!
Peter B. Peter B.
Sep 6, 2023 12:00:10 PM
Summary: We had a wonderful stay at this beautiful house on the ocean. Everything was so perfect for our small work retreat. The only issue we had at all was the downstairs bed was very hard. A memory foam mattress added would fix it and make his house absolutely perfect! Thank you for sharing your beautiful home!
Karen H. Karen H.
Aug 13, 2023 03:52:45 AM
Summary: Rudman's Retreat provided the quintessential Maine vacation. This is what made it perfect: a bright comfortable house, with a fully stocked kitchen, a dock to watch the sunset over the cove, a 5 minute walk to the the beach, and a super friendly and attentive host. Of the many properties we have rented Rudman's Retreat is at the top of the list.
Jan O. Jan O.
Nov 23, 2022 01:00:30 PM
Summary: Amazing property. Enjoyed our stay.
Ben R. Ben R.

FAQ's

Is this Bailey Island house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Bailey Island house have a swimming pool?

No, this Bailey Island house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Bailey Island house?

Best-rates for the Bailey Island house starts from $335 per night with includes Laundry, TV, Balcony/Terrace, Bedding/Linens, Guest Services, Entertainment, Barbecue/Outdoor Cooking, Parking, Security/Safety, Fireplace/Heating, Internet, Sports/Activities, Child Friendly, Air Conditioner, Wellness Facilities, Kitchen StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Bailey Island house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Bailey Island house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Bailey Island house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Bailey Island house?

Based on the information reported by the owner or manager, the Bailey Island house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Bailey Island house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Bailey Island house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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