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Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views.

Photo gallery for Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views.

House view from the driveway.
Daily sunsets from the house, deck, balcony or pier.
Pathway to the pier over deep water frontage.
Kitchen looking at Master Bedroom Loft space and entrance to downstairs hall.
Livingroom from front entrance.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 61790 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Harpswell, ME
  • Place, Land's End Gift Shop
    ‪2 min walk‬
  • Place, Mackerel Cove
    ‪5 min walk‬
  • Place, LL Bean Flagship Store
    ‪47 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪71 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Downstairs Bedroom

1 Queen Bed

Office 1

1 Double Sofa Bed

Upstairs Bedroom

1 Queen Bed

2 bathrooms

Bathroom 1 Downstairs

Towels provided · Bathtub or shower · Toilet

Bathroom 2, Master Bedroom

Towels provided · Bidet · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views.

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

Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor Space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 22
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
Owner allows NO exceptions due to health reasons
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Smoking

Smoking is not permitted

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher

We should mention

This property does not have elevators

About the neighborhood

Bailey Island

Located in Bailey Island, this vacation home is on the waterfront. Maine Street and LL Bean Flagship Store are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Brunswick Town Commons and Casco Bay. Land's End Gift Shop and Paddleworks are also worth visiting. Sailing and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking/biking trails nearby.
View more Vacation Homes in Bailey IslandOpens in a new window
Map
Harpswell, ME

What's nearby

  • Land's End Gift Shop - 2 min walk - 0.2 km
  • Mackerel Cove - 5 min walk - 0.5 km
  • Bailey Island Bridge - 7 min drive - 4.3 km
  • Bowdoin College - 35 min drive - 30.0 km
  • LL Bean Flagship Store - 47 min drive - 53.0 km

Getting around

  • Brunswick Station - 34 min drive
  • Portland Intl. Jetport Airport (PWM) - 61 min drive

Restaurants

  • ‪Cook's Lobster & Ale House - ‬5 min drive
  • ‪Erica's Seafood & Lobster Shop - ‬35 min drive
  • ‪Dolphin Marina & Restaurant - ‬35 min drive
  • ‪B.I.G.S. Bailey Island General Store - ‬2 min drive
  • ‪Allen's Seafood - ‬22 min drive

Frequently asked questions

Is Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. ?

As of Mar 10, 2026, prices found for a 1-night stay for 2 adults at Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. on Apr 29, 2026 start from $301, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. ?

Check-in begins at 4:00 PM.

What time is check-out at Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. ?

Check-out is at 10:00 AM.

Where is Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views. located?

Situated on the waterfront, this vacation home is within a 5-minute walk of Land's End Gift Shop and Mackerel Cove. Casco Bay and Bailey Island Bridge are also within 3 mi (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 52 out of 58 reviews
Rating 8 - Good. 5 out of 58 reviews
Rating 6 - Okay. 1 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 0 out of 58 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Sarah C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Long weekend vacation

We enjoyed our stay! The property had a great view of the sunset.
Stayed 3 nights in Aug 2024

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Location

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!
Stayed 4 nights in May 2024

10/10 Excellent

Eric M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Remote and relaxing.

We had a great time observing the locals.Those that aren't catching lobsters are serving them in their local restaurants.
Stayed 6 nights in Dec 2024

6/10 Okay

Bradford H.

Liked: Cleanliness, check-in, communication, location

Review

Overall, great property. Disappointed gas stove was not functional.
Stayed 3 nights in Apr 2025

10/10 Excellent

Jeremy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and peaceful location

We spent a week in late May at the house. The house was clean and well stocked - nothing lacking. The location is perfect, at the tip of Bailey island - very quiet. Would return there again for relaxation or work from home-from-home.
Stayed 7 nights in May 2021

10/10 Excellent

Jan O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Maine Perfection

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.
Stayed 7 nights in Jul 2023

10/10 Excellent

Karen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Stay

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!
Stayed 3 nights in Aug 2023

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Didn't really want to leave

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!).
Stayed 14 nights in Jul 2024

8/10 Good

Maura T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Place but Construction Noise

The house is very nice and accurately represented by the photos. Very clean and well equipped and the view and sunsets were beautiful. However, the house next door is building an addition and the construction noise was pretty constant from 7:30 AM until about 5:00 PM.
Stayed 4 nights in Jun 2021

10/10 Excellent

Peter B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful 2nd time stay at a gorgeous property

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!
Stayed 7 nights in May 2024

10/10 Excellent

michael u.

Liked: Cleanliness, check-in, communication, location, listing accuracy

left behind?

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
Stayed 7 nights in Jul 2024

10/10 Excellent

Elizabeth N.

Gorgeous views from bright and spacious home

We loved our stay at Rudman's Retreat. David was a pleasure to deal with and just down the road for any questions. The house was very clean and comfortable and the views from almost every room were awesome. We loved watching the parade of fishing boats, sail boats and even a ferry going by while sitting out on the deck for breakfast and dinner. House has all the conveniences we wanted including a washer and dryer and WIFI. Having two bathrooms is really handy for getting ready in the morning. There's a great spot in the study to work at the desk overlooking the ocean should you need to. I admit to falling in love with the flock of turkeys that made daily appearances. Bailey Island has some great restaurants just a short drive away where you can eat in or do take away and eat on your deck. We did both. The strawberry shortcake at Cooks was amazing. It's the first I've had that I preferred to my homemade! We would happily recommend this place to others.
Stayed 7 nights in Sep 2018

10/10 Excellent

Ben R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Amazing property. Enjoyed our stay.
Stayed 6 nights in Oct 2022

8/10 Good

Keith H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good but some attention needed

Great location. In general the property is good but it is a little tired in a few respects.
Stayed 7 nights in Sep 2022

10/10 Excellent

Jill S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Seamless Stay

Location is lovely, home is clean and comfortable and rental process was easy.
Stayed 3 nights in May 2022

10/10 Excellent

suzanne s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just what the Dr ordered!

We arrived and it was instant balm for the soul, the water is closer than appeared. The home is open and airy and had all you could need. We enjoyed our winter break home away from home....Thank you.
Stayed 7 nights in Feb 2022

10/10 Excellent

Fiyel L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Cottage

Love this place. It was our second time staying here. It's well maintained, very clean and tidy, and incredibly cozy. Lovely for a winter week in nature.
Stayed 4 nights in Dec 2021

10/10 Excellent

Martin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bailey Island retreat is a perfect Christmas home

The serene and lovely views matched with just enough snow on Christmas Day to make everything a bit magical. The well supplied kitchen made our dinner a breeze.
Stayed 6 nights in Dec 2021

10/10 Excellent

Elizabeth Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rudman Review from BZ

This was Nirvana. Reserving this property next year. We didn’t want to leave. Perfect location. Peaceful, beautiful. Can’t say enough about how wonderful it is!
Stayed 6 nights in Oct 2021

10/10 Excellent

DIANE D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bailey Island beauty

The property was better than the pictures! Stocked with all the necessities, very clean and comfortable. So peaceful and relaxing. Loved the family of turkeys that visited every day. Will definitely rent this house again.
Stayed 7 nights in Sep 2021

10/10 Excellent

Jamie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Rudman’s Retreat

Second time we’ve rented Rudman’s Retreat… love the setting overlooking outer Mackeral Cove. House is well equipped, comfortable, and in a quiet area. Enjoy watching the lobsterman come out in am to pull traps.
Stayed 7 nights in Jul 2021

10/10 Excellent

Susan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Baileys Island

Wonderful stay.
Stayed 3 nights in May 2021

8/10 Good

Steve W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home, beautiful location

The process was smooth and simple, the property gorgeous. Our only complaint was that we were awakened by jack hammers next door each morning at 7:30. Not ideal, especially in coming from a western time zone.
Stayed 2 nights in Apr 2021

10/10 Excellent

Joel R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Retreat review

Everything we hoped for. Relaxing, quiet, sunsets and salt air. Well appointed, clean and comfortable.
Stayed 4 nights in Apr 2021

10/10 Excellent

Nancy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quintessential Maine

Nestled into a hill on the rocky coast of Maine made for a quiet and relaxing vacation. Wonderful views of the sea to watch the tides, gulls, and lobster boats go by. House was well-equipped with everything that we needed.
Stayed 7 nights in Apr 2021

About the host

Hosted by David Johnson

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