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Five Islands Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Five Islands vacation rentals

Outdoor dining

1. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is ￥16,448
￥26,507 total
includes taxes & fees
Aug 5 - Aug 6
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Terrace/patio

2. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is ￥20,399
￥31,327 total
includes taxes & fees
Aug 4 - Aug 5
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Desk, iron/ironing board, WiFi (free), bed sheets

3. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is ￥43,008
￥74,416 total
includes taxes & fees
Aug 31 - Sep 1
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Interior

4. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is ￥18,416
￥38,259 total
includes taxes & fees
Sep 2 - Sep 3
Modern style in historic building in downtown Bath
TV

5. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥28,922
￥47,620 total
includes taxes & fees
Aug 28 - Aug 29
Mid Coast Getaway w/ water views
Property grounds

6. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.8 out of 10, Good, (15 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is ￥22,430
￥27,881 total
includes taxes & fees
Aug 5 - Aug 6
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Property grounds

7. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is ￥21,249
￥32,426 total
includes taxes & fees
Sep 1 - Sep 2
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Exterior

8. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (158 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is ￥20,785
￥26,086 total
includes taxes & fees
Sep 2 - Sep 3
Large suite/private bath/private entrance on quiet street near Thomas Bay
Terrace/patio

9. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.4 out of 10, Very Good, (6 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is ￥23,453
￥35,171 total
includes taxes & fees
Aug 10 - Aug 11
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Property grounds

10. Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is ￥65,617
￥102,663 total
includes taxes & fees
Aug 30 - Aug 31
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Property grounds

11. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
The price is ￥37,776
￥66,053 total
includes taxes & fees
Aug 5 - Aug 6
Boothbay Harbor, 2-Story Cottage, downtown
Beach nearby

12. Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
The price is ￥30,300
￥53,273 total
includes taxes & fees
Aug 6 - Aug 7
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Outdoor dining

13. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is ￥14,638
￥34,223 total
includes taxes & fees
Aug 10 - Aug 11
Happy Cottage Near Everything 11
Coffee/tea maker, fridge, microwave, stovetop

14. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is ￥17,629
￥39,316 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 1 Bedroom Cottage Close to Everything 5
Terrace/patio

15. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
8.0 out of 10, Very Good, (2 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is ￥22,666
￥35,171 total
includes taxes & fees
Aug 10 - Aug 11
Renovated The Driftwood Cabin at White Anchor Inn
2 bedrooms, iron/ironing board, bed sheets

16. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is ￥19,360
￥41,374 total
includes taxes & fees
Aug 5 - Aug 6
Cheerful Cottage with Loft 9
Exterior

17. Historic Bath's, Home Away from Home

Historic Bath's, Home Away from Home
Bath
The price is ￥24,084
￥68,499 total
includes taxes & fees
Aug 7 - Aug 8
Historic Bath's, Home Away from Home
Exterior detail

18. Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
9.8 out of 10, Exceptional, (6 reviews)
"Nice tree surrounded property. We also woke up to snow which made the setting magical."
United States
lisa s.
The price is ￥30,300
￥66,998 total
includes taxes & fees
Aug 9 - Aug 10
Tiny A-Frame Romantic Getaway
Coffee/tea maker, fridge, microwave, oven

19. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (30 reviews)
"Close enough to BoothBay Harbour and Botanical Gardens but private and quiet get away. Very comfortable! Spacious, good appliances and bedding. I would guess very new. Loved it!"
United States
Judith
The price is ￥42,356
￥91,976 total
includes taxes & fees
Aug 4 - Aug 5
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Terrace/patio

20. Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
Tide Haven Cottage on Bay Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Five Islands Hotel Reviews

Smuggler's Cove Inn

Smuggler's Cove Inn

8/10 Good
"Clean room, pet friendly, breakfast good. Location great with lots of amenities. Beds comfortable"
Georgia 2-night trip
Posted less than an hour ago
Smuggler's Cove Inn

Find out more about Five Islands

Search for holiday rentals in Five Islands on Expedia! You can easily find your home rentals, villas, holiday apartments in Five Islands using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Five Islands while they last

Look no further and take a look at our great range of rental properties in Five Islands!

Frequently asked questions

Can I find a vacation rental in Five Islands?

Yes, you can find vacation rentals near well known attractions in Five Islands, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Five Islands?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: Visitors like this Five Islands vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Five Islands?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Five Islands stay.

What’s there to see and do in Five Islands?

Explore the area and family-friendly sights such as Boothbay Railway Village, or get out into nature at a spot like Coastal Maine Botanical Gardens. In the larger area, you’ll find Reid State Park and Hodgdon Island.

What’s a vacation rental in Five Islands like?

A vacation rental is a private property where you can stay for short or long periods in Five Islands. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.