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Waldoboro Vacation Rentals

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Bedrooms

Bathrooms

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Distance from

5 mi
36 rentals in Waldoboro.
Farmstay, 2 bedrooms with 2 private baths, private entrance., vacation rental in Waldoboro
Farmstay, 2 bedrooms with 2 private baths, private entrance., vacation rental in Waldoboro
Farmstay, 2 bedrooms with 2 private baths, private entrance., vacation rental in Waldoboro

Farmstay, 2 bedrooms with 2 private baths, private entrance.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront, Breathtaking Views, Patio Fireplace, Chefs Kitchen, HGTV remodel, vacation rental in Waldoboro
Waterfront, Breathtaking Views, Patio Fireplace, Chefs Kitchen, HGTV remodel, vacation rental in Waldoboro
Waterfront, Breathtaking Views, Patio Fireplace, Chefs Kitchen, HGTV remodel, vacation rental in Waldoboro

Waterfront, Breathtaking Views, Patio Fireplace, Chefs Kitchen, HGTV remodel

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Entire Waldoboro Inn, vacation rental in Waldoboro
The Entire Waldoboro Inn, vacation rental in Waldoboro
The Entire Waldoboro Inn, vacation rental in Waldoboro

The Entire Waldoboro Inn

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Waldoboro Inn Room 5, vacation rental in Waldoboro
The Waldoboro Inn Room 5, vacation rental in Waldoboro
The Waldoboro Inn Room 5, vacation rental in Waldoboro

The Waldoboro Inn Room 5

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Waldoboro Inn Room 3, vacation rental in Waldoboro
The Waldoboro Inn Room 3, vacation rental in Waldoboro
The Waldoboro Inn Room 3, vacation rental in Waldoboro

The Waldoboro Inn Room 3

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Waldoboro Inn Room 1, vacation rental in Waldoboro
The Waldoboro Inn Room 1, vacation rental in Waldoboro
The Waldoboro Inn Room 1, vacation rental in Waldoboro

The Waldoboro Inn Room 1

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly-built waterfront home with fast WiFi, furnished deck, & washer/dryer, vacation rental in Waldoboro
Newly-built waterfront home with fast WiFi, furnished deck, & washer/dryer, vacation rental in Waldoboro
Newly-built waterfront home with fast WiFi, furnished deck, & washer/dryer, vacation rental in Waldoboro

Newly-built waterfront home with fast WiFi, furnished deck, & washer/dryer

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Just steps to the water with beautiful sunsets! Now booking for 2025!, vacation rental in Waldoboro
Just steps to the water with beautiful sunsets! Now booking for 2025!, vacation rental in Waldoboro
Just steps to the water with beautiful sunsets! Now booking for 2025!, vacation rental in Waldoboro

Just steps to the water with beautiful sunsets! Now booking for 2025!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Small But Mighty (Elegant) Rural Retreat, vacation rental in Waldoboro
Small But Mighty (Elegant) Rural Retreat, vacation rental in Waldoboro
Small But Mighty (Elegant) Rural Retreat, vacation rental in Waldoboro

Small But Mighty (Elegant) Rural Retreat

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Dog Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy, vacation rental in Waldoboro
Charming Dog Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy, vacation rental in Waldoboro
Charming Dog Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy, vacation rental in Waldoboro

Charming Dog Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bdrm - Bird Song Retreat - Beach Days & Stargazed Nights!, vacation rental in Waldoboro
2 Bdrm - Bird Song Retreat - Beach Days & Stargazed Nights!, vacation rental in Waldoboro
2 Bdrm - Bird Song Retreat - Beach Days & Stargazed Nights!, vacation rental in Waldoboro

2 Bdrm - Bird Song Retreat - Beach Days & Stargazed Nights!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Waldoboro House Near Lakes, Boating, Etc!, vacation rental in Waldoboro
Historic Waldoboro House Near Lakes, Boating, Etc!, vacation rental in Waldoboro
Historic Waldoboro House Near Lakes, Boating, Etc!, vacation rental in Waldoboro

Historic Waldoboro House Near Lakes, Boating, Etc!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Come and relax in Mid Coast Maine. We are child and pet friendly., vacation rental in Waldoboro
Come and relax in Mid Coast Maine. We are child and pet friendly., vacation rental in Waldoboro
Come and relax in Mid Coast Maine. We are child and pet friendly., vacation rental in Waldoboro

Come and relax in Mid Coast Maine. We are child and pet friendly.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet quaint cape house nestled between two coves, vacation rental in Waldoboro
Quiet quaint cape house nestled between two coves, vacation rental in Waldoboro
Quiet quaint cape house nestled between two coves, vacation rental in Waldoboro

Quiet quaint cape house nestled between two coves

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Waterfront Cottage with Great Views, Sunsets, vacation rental in Waldoboro
Lovely Waterfront Cottage with Great Views, Sunsets, vacation rental in Waldoboro
Lovely Waterfront Cottage with Great Views, Sunsets, vacation rental in Waldoboro

Lovely Waterfront Cottage with Great Views, Sunsets

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private riverfront retreat with foosball & firepit - overlooks nature preserve, vacation rental in Waldoboro
Private riverfront retreat with foosball & firepit - overlooks nature preserve, vacation rental in Waldoboro
Private riverfront retreat with foosball & firepit - overlooks nature preserve, vacation rental in Waldoboro

Private riverfront retreat with foosball & firepit - overlooks nature preserve

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historical Retreat  in the heart of Midcoast Maine, vacation rental in Waldoboro
Historical Retreat  in the heart of Midcoast Maine, vacation rental in Waldoboro
Historical Retreat  in the heart of Midcoast Maine, vacation rental in Waldoboro

Historical Retreat in the heart of Midcoast Maine

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access, vacation rental in Waldoboro
Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access, vacation rental in Waldoboro
Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access, vacation rental in Waldoboro

Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3 Brdm - Easy Access to Explore all of Maine!, vacation rental in Waldoboro
3 Brdm - Easy Access to Explore all of Maine!, vacation rental in Waldoboro
3 Brdm - Easy Access to Explore all of Maine!, vacation rental in Waldoboro

3 Brdm - Easy Access to Explore all of Maine!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Idyllic Post & Beam Cottage On Quiet Fresh Water Lake, vacation rental in Waldoboro
Idyllic Post & Beam Cottage On Quiet Fresh Water Lake, vacation rental in Waldoboro
Idyllic Post & Beam Cottage On Quiet Fresh Water Lake, vacation rental in Waldoboro

Idyllic Post & Beam Cottage On Quiet Fresh Water Lake

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Wonderful Cape with Stunning Waterviews and Sunsets, vacation rental in Waldoboro
Wonderful Cape with Stunning Waterviews and Sunsets, vacation rental in Waldoboro
Wonderful Cape with Stunning Waterviews and Sunsets, vacation rental in Waldoboro

Wonderful Cape with Stunning Waterviews and Sunsets

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Idyllic waterfront home with furnished deck, grill, sweeping views & private, vacation rental in Waldoboro
Idyllic waterfront home with furnished deck, grill, sweeping views & private, vacation rental in Waldoboro
Idyllic waterfront home with furnished deck, grill, sweeping views & private, vacation rental in Waldoboro

Idyllic waterfront home with furnished deck, grill, sweeping views & private

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Setting with Water Front view and 5-star Amenities, vacation rental in Waldoboro
Private Setting with Water Front view and 5-star Amenities, vacation rental in Waldoboro
Private Setting with Water Front view and 5-star Amenities, vacation rental in Waldoboro

Private Setting with Water Front view and 5-star Amenities

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Water Front post and beam guest house "Thyme & Tide", on Muscongus Bay., vacation rental in Waldoboro
Water Front post and beam guest house "Thyme & Tide", on Muscongus Bay., vacation rental in Waldoboro
Water Front post and beam guest house "Thyme & Tide", on Muscongus Bay., vacation rental in Waldoboro

Water Front post and beam guest house "Thyme & Tide", on Muscongus Bay.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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5 Bdrm, 2+ Baths as of Feb 2025, C notes inside., vacation rental in Waldoboro
5 Bdrm, 2+ Baths as of Feb 2025, C notes inside., vacation rental in Waldoboro
5 Bdrm, 2+ Baths as of Feb 2025, C notes inside., vacation rental in Waldoboro

5 Bdrm, 2+ Baths as of Feb 2025, C notes inside.

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch, vacation rental in Waldoboro
Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch, vacation rental in Waldoboro
Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch, vacation rental in Waldoboro

Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch

Rental Home
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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7 BDRM - Spacious Hilltop Retreat for Unforgettable Gatherings, vacation rental in Waldoboro
7 BDRM - Spacious Hilltop Retreat for Unforgettable Gatherings, vacation rental in Waldoboro
7 BDRM - Spacious Hilltop Retreat for Unforgettable Gatherings, vacation rental in Waldoboro

7 BDRM - Spacious Hilltop Retreat for Unforgettable Gatherings

Condo/Apartment
7 bedrooms
4 bathrooms
Sleeps 19
Match: Sleeps
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Two wonderful homes on the river with fast WiFi, furnished decks, grills & W/D, vacation rental in Waldoboro
Two wonderful homes on the river with fast WiFi, furnished decks, grills & W/D, vacation rental in Waldoboro
Two wonderful homes on the river with fast WiFi, furnished decks, grills & W/D, vacation rental in Waldoboro

Two wonderful homes on the river with fast WiFi, furnished decks, grills & W/D

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Quiet & cozy ocean-side hideaway. Pet friendly!, vacation rental in Waldoboro
Quiet & cozy ocean-side hideaway. Pet friendly!, vacation rental in Waldoboro
Quiet & cozy ocean-side hideaway. Pet friendly!, vacation rental in Waldoboro

Quiet & cozy ocean-side hideaway. Pet friendly!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A Charming Getaway with Stunning Views and Modern Conveniences, vacation rental in Waldoboro
A Charming Getaway with Stunning Views and Modern Conveniences, vacation rental in Waldoboro
A Charming Getaway with Stunning Views and Modern Conveniences, vacation rental in Waldoboro

A Charming Getaway with Stunning Views and Modern Conveniences

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Thistledown Farm's Sheep Shed Cottage, vacation rental in Waldoboro
Thistledown Farm's Sheep Shed Cottage, vacation rental in Waldoboro
Thistledown Farm's Sheep Shed Cottage, vacation rental in Waldoboro

Thistledown Farm's Sheep Shed Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Thistledown Farm's Udder Heaven, vacation rental in Waldoboro
Thistledown Farm's Udder Heaven, vacation rental in Waldoboro
Thistledown Farm's Udder Heaven, vacation rental in Waldoboro

Thistledown Farm's Udder Heaven

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront, dog-friendly suite with Broad Cove access, firepit & sunrise view, vacation rental in Waldoboro
Waterfront, dog-friendly suite with Broad Cove access, firepit & sunrise view, vacation rental in Waldoboro
Waterfront, dog-friendly suite with Broad Cove access, firepit & sunrise view, vacation rental in Waldoboro

Waterfront, dog-friendly suite with Broad Cove access, firepit & sunrise view

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Sea Heather Cottage, beautiful Maine home on a peninsula surrounded by nature, vacation rental in Waldoboro
Sea Heather Cottage, beautiful Maine home on a peninsula surrounded by nature, vacation rental in Waldoboro
Sea Heather Cottage, beautiful Maine home on a peninsula surrounded by nature, vacation rental in Waldoboro

Sea Heather Cottage, beautiful Maine home on a peninsula surrounded by nature

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Creative winter and spring on a river in Maine, vacation rental in Waldoboro
Creative winter and spring on a river in Maine, vacation rental in Waldoboro
Creative winter and spring on a river in Maine, vacation rental in Waldoboro

Creative winter and spring on a river in Maine

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming Historic Loft Apartment in Waldoboro. Once an Army Post & Dance Hall., vacation rental in Waldoboro
Charming Historic Loft Apartment in Waldoboro. Once an Army Post & Dance Hall., vacation rental in Waldoboro
Charming Historic Loft Apartment in Waldoboro. Once an Army Post & Dance Hall., vacation rental in Waldoboro

Charming Historic Loft Apartment in Waldoboro. Once an Army Post & Dance Hall.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-36 of 36
Frequently Asked Questions about Waldoboro